THE 5 BEST Horseback Riding Tours in Hudson River Valley, NY

Horseback riding tours in hudson river valley.

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1. Westchester Trail Rides

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2. Mohonk Mountain House Hudson Valley Day Trips

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3. Ivy Rock Farms

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4. Friendship Equestrian Center

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6. Meadow Creek Farm

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15 Places to Learn to Ride a Horse in the Hudson Valley

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A lot of us will be looking for new adventures this summer. You may even be thinking that it is time to take something off your bucket list. If horseback riding is something you have been thinking about I have found some great places throughout the Hudson Valley that can get you started.

The Hudson Valley is rich with places that can teach you to ride if that's what you are looking to do. There are also many places that will take you out on trails if you think that horseback riding may just be a one-time thing for you and some friends. No matter what you are hoping to accomplish there is a good chance that one of the places I have listed below can help your horse wish list come true.

I grew up loving horses and was one of those kids who asked my parents for a horse every year until they finally broke down and got me one. They also finally realized that me having one and working at the barn where we boarded my horse was cheaper than me just taking lessons every week.

So whether you are looking for a trail ride with friends or you are hoping to get in the saddle and compete don't hold back on that dream any longer. There is a Hudson Valley horse waiting for you and ready to make your horseback riding dreams come true. Happy Trails.

Horseback Riding Facilities in the Hudson Valley

Mohonk Stables - High Falls 845 256-2784

Juckas Stables - Pine Bush 845 361 1429

Lucky C Stables - New Paltz 845 255 3220

Gardnertown Farms - Newburgh 845 564 6658

Crosswinds Equestrian Center - Lagrangeville 845 223 7433

Ashokan Horseback Riding Club  - Olivebridge: 845 657 8021

Westchester Trail Rides - Croton-on-Hudson: 914 539 2987

Netherwood Acres - Hyde Park: 845 392 5639

Mountain Valley Farm - Millerton 212 888 8545

Tullin Ranch - Saugerties 845 481 4321

Friendship Equestrian Center and Hudson on Horseback  - Hudson: 518 821 8555

Horses for a Change - Esopus 845 384 6424

Southlands Foundation - Rhinebeck 845 876 4862

Meadow Creek Farm - Pleasant Valley 845 363 6000

Ivy Rock Farms - New Windsor 845-534 0365

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Mountain Valley Farm

Millerton, New York. Western Horseback Riding Adventures

A unique horse farm that provides western horseback riding, AirBnB's, rustic events & skeet shooting located in a historic, vibrant Hudson Valley village, bustling with restaurants, cozy cafes and boutiques shops - Millerton, New York.

With access to more than 4000 acres of trails with sweeping vistas along the Hudson Valley and the Berkshires – whether you are a casual rider looking for a riding adventure, round pen lessons or skeet shooting, our services are available to you.

Come and visit the farm!

Experiences

What we offer, stay at the farm, see our stay offers, organize an event, trail riding.

Mountain Valley Farm - Millerton New York 223

Trail Riding | 1 Hour

If you’re looking for a fun day out in the Hudson Valley, with friends or family, our private horseback trail rides are a perfect adventure.

Mountain Valley Farm - Millerton NY Ranch Horse Riding

Trail Riding | 1.5 Hour

This private ride will take you on an extended adventure through the foothills of the Berkshires.

Mountain Valley Farm - Millerton New York 159

Trail Riding | 2 Hours

On our most popular private trail ride adventure. You’ll explore stunning nature, amazing views of the Catskills and Berkshires.

Special experiences

Mountain Valley Farm - Millerton NY Horseback Riding Lessons

Round Pen Lesson

Private Round Pen Lessons for kids and adults, offer a unique opportunity to connect with your horse and improve skills sets.

Mountain Valley Farm - Millerton New York 185

Skeet Shooting

There are very few sports in life as exciting as clay pigeon shooting! It is the perfect activity for all skill levels and ages!

Mountain Valley Farm - Sunset Horseback Trail Ride Millerton New York 02

Trail Riding | Sunset Ride

Expect spectacular lighting on this private adventure during the ‘golden hours’! Perfect date or bring the whole family. Please inquire for any special requests.

Mountain Valley Farm Ranch - NY Accommodation - The Ranch

City Slickers Dream Getaway! Large 3 bedroom Farm House nestled on a real working horse ranch. The property operates a western horseback riding & skeet shooting for Beginners to Experts on over 1500 acres of gorgeous trails which overlook the Catskills and the Berkshires.

The Stables & Barn are also available for corporate events, rustic events and weddings. The farm has many woodland creatures that pass through from wild turkeys, woodpeckers, owls & families of deer. Perfect for those who want to be surrounded in nature.

The Overlook

There is a large family room, full kitchen, two desks with office chairs, jetted spa for a luxurious soak. 1 Full Bath with separate shower.

The property has many amenities such as firepit, wifi, full kitchen, grill and plenty of parking.

Mountaina Valley Farm - Millerton NY - Accomodation - The Overlook

Best Horseback Riding Adventures

Skeet shooting is a sport that tests the marksmanship of a shooter. In skeet shooting a clay pigeon or target is flung through the air and the shooter attempts to hit it.

Mountain Valley Farm - Millerton New York Skeet Shooting

Things to Pack for a Horseback Trek

A good hat – riding in a helmet is always advised, but we know some people don’t. Especially on slower trails and riding Western, folks seem to think it’s less important, which is untrue.

Mountain Valley Farm - New York Milerton - Things To Pack For A Horseback Trek

Going on a trail ride is a popular way for both beginner and experienced riders to enjoy time out in nature on horseback. In this post, we explore the history…

Mountain Valley Farm New York - Millerton NY Trail Riding

Horseback Riding Essentials

You are high above the ground, astride a leather seat perched on a living, breathing animal. You’re not too sure how to control it – or whether it would even listen to you if you tried.

Mountain Valley Farm NY - Must Know Things Before Going Horseback Riding

Horseback Riding Adventures at Mountain Valley Farm – Millerton, New York

With access to more than 4000 acres of trails with sweeping vistas along the Hudson Valley and the Berkshires.  Whether you are a casual rider looking for horseback riding adventures, trail riding, round pen lessons or even skeet shooting, our services are available to you. Come and  stay at the farm  for the ultimate experience. See our  services for more information on what we can offer you.

+1 212 888 8545

OPEN YEAR ROUND

Juckas Riding Stables

  • Most Popular Ride!

45 Minute Trail Ride

Quick Details

Duration: 45 minute Schedule: Daily (some days require call-to-book) Time: If you don’t find the time you wanted on our schedule please call to book (845)-361-1429 Ages: 7+ Weight Limit: 250 lbs, For the safety of yourself, the group and our horses, please put an accurate, current weight. Experience: No prior riding experience necessary. What to bring: Closed-toe shoes, comfortable jeans, appropriate clothing for the season.

Saddle up and head out on our 45 Minute Trail Ride!

Planning on horseback riding New York? You’ve come to the right place! Juckas Stables is your premier Hudson Valley horseback riding location for experienced riders and beginners! Start off with our 45 minute trail ride, led by one of our experienced and friendly guides. Let us match you with the right horse and help you with everything from adjusting your saddle and stirrups to mounting and dismounting.

Our experienced wranglers begin the trail ride with a quick lesson to ensure a fun and safe trail ride. Follow your guide around our gorgeous farmlands, featuring 117 acres that wind through the peaceful and breathtaking Hudson Valley countryside. Ride with us as we traverse sunny fields and shaded woods, forests, and ponds. Look for wildlife like birds, snapping turtles and deer.

Our horses are gentle, responsive, and well-trained.  Join us for a the pleasure of horseback riding and a slice of nature. Reserve your horse today.

a person lying on the ground

Related Trail Rides

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  • Clock 75 minutes

75 Minute Trail Ride

Join us for a longer trail ride, the best option for those who want to spend more time on their horse and explore all the countryside and farmland we have to offer. Saddle up and join us!

TripAdvisor Rated #1 All-Inclusive Family Resort in the US

Reservations 800-647-2624 | View Your Reservation

All-Inclusive Senior Group Tours in the Historic Hudson Valley!

Autumn brings brilliant fall foliage, and partnered with our Fall Fest Wine and Cheese Parties, the combination will delight your senses. With Spring and Summer’s arrival comes our lush, award winning gardens. Take a stroll by our private lake, and take in the magnificent scenery we have to offer.

Horseback Riding

Our beautiful Riding Trails are open year-round. Each season offers its own unique beauty to discover! Horseback riding for beginners to the advanced, including riding demonstrations and instruction. Click here to see more horse activities.

Activities on our Private Lake

Our beautiful private lake provides a scenic backdrop for your group’s next big adventure. Start with some shuffleboard, bocce or simply stroll our award winning gardens. Then make your way to our tennis courts or hop on one of our paddle boats for a leisurely ride. Click here to see more outdoor activities.

Nightly Entertainment

Live performances in the Silverado Saloon will keep you dancing the night away. Enjoy our featured comedians and magicians from around the world. Click here to see all entertainment.

Tour the Historic Hudson Valley

Visit the Walkway Over the Hudson, with spectacular 360° panoramic views of the Hudson River and surrounding mountains, only minutes away with complimentary shuttle service. Click here to see more area attractions.

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Ready to book your senior group trip.

Contact Nikki, Group Sales Representative (800) 647-2624  Ext 1031 | nikki@rhranch.com

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Best places to ride a horse in the Hudson Valley

Delight the horse lover in your family.

Best places to ride a horse in the Hudson Valley

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Active Riding Trips

New York’s Training and Trail Riding in Hudson Valley

  • Jan - Feb - Mar - Apr - May - Jun - Jul - Aug - Sep - Oct - Nov - Dec
  • Breakfast Included

Ride Overview

Nestled in the rolling hills of hunt country in the Hudson Valley of NY, Rounded Crest Farm offers riders of all ages and abilities the chance to “have it all”. Set in a pastoral area, the farm has large indoor and outdoor arenas as well as a small field of natural obstacles. And for riders that want to get out of the arena, there are miles of wide open groomed trails for hacking. You’ll spend the week with Ericka Rose – the “Galloping Guru”, she is a true gem, and a fabulous resource on all matters related to riding and horsemanship.

Daily instruction is tailored to meet the goals of the rider and offered by both Ericka and her incredible team. A few days at Rounded Crest Farm find most riders happy, tired and with clear breakthroughs in their progress. Her group of 50+ horses are well schooled and fun

Ericka has over 30 years of professional riding, showing, foxhunting and working with clients and is a member of several hunts on the east coast. The program offers lessons in flatwork/dressage, jumping, XC and trail riding. Fox hunting – or learn to fox hunt programs are also available.

This program is offered on a 5 day basis: Monday-Friday; or on a 3 day basis: Friday-Sunday. Accommodations are not included but we are happy to help with recommendations!

Dates: Open all year

Rates: Daily – $570.00 USD includes 3-4 hours of lessons/hacking

Hunting can be arranged from Aug-Dec. 26 with Millbrook, Old Chatham and Windy Hollow hunts. And from January-March in South Carolina and Georgia. Formal attire required. Cap Fees range from $100.00-$250.00 USD.

  • Daily riding - lessons or trail riding
  • Horse and all tack
  • Instruction/guiding
  • Horse transport for some trails
  • All local taxes

Not Included

  • Accommodation
  • Travel Insurance
  • Transfers to/from the farm (rental car required)
  • Lunches and dinners
  • Gratuities for the team at the end of the stay

New-York-Hudson-Valley-map

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Horseback Riding at Schunnemunk Shadow Stables – Ivy Rock Farm

Our convenient locations between train stations and bus stops make us easily accessible to our Manhattan customers – only 60 miles North of NYC. Our local customers find our facilities ideal as we are within 10 minutes of major routes and highways like 17, 9W, 84 and the NYS Thruway. We even offer a Guest House for our traveling horses & owners or for vacation getaways. Come visit and experience Ivy Rock Farms for yourself…you won’t be disappointed!

Enjoy the Hudson Valley

riding tour hudson valley

Sunday, June 23, 2024

Check out Photo Highlights

Important details.

  • Rain or shine
  • This event takes place on streets open to traffic.
  • Helmets are required on all Bike New York rides.
  • New York State law requires that all cyclists have and use a bike bell or horn.
  • Proceeds from all Bike New York events help to fund our free bike education programs. Learn more .

Discover Hudson Valley Ride

All routes begin and end in Victor C. Waryas Park in Poughkeepsie, NY —right next to the Metro-North train station.

NEW FOR THIS YEAR :  The Walkway Over the Hudson and the Hudson Valley Rail Trail will be open to Discover Hudson riders only!

We strongly encourage you to start riding within the first 15 minutes of your route’s timeframe – the streets heading out of Waryas Park will be closed to vehicular traffic during the first 15 minutes of each start window to ensure your day starts smoothly:

  • 100 mile riders – 7:30-7:45AM
  • 75 mile riders – 8:00-8:15AM
  • 50 mile riders – 8:30-8:45AM
  • 33 mile riders – 9:15-9:30AM
  • 15 mile riders – 9:30-9:45AM

Please refer below for start time windows and route summaries. Be advised that you cannot join a route prior to the specific window opening or after it has closed.

NOTE : If you miss your intended timeframe, you must drop back to a shorter mileage. Timing is based on the availability of route support and services.

This family-friendly route option takes riders across the Hudson via the Walkway and onto the tranquil rail trail and scenic backroads of Ulster County before circling back over the river and into Waryas Park in Poughkeepsie, NY.

Elevation :  895 feet

Start time :  9:30AM – 10:15AM

Same as the 15-mile route with an additional 18-mile loop on the backroads of Dutchess County.

Elevation :  1,754 feet

Start time :  9:15AM – 10:15AM

The 55-mile route begins like the 15 and 33-mile but veers south after the first rest stop in Ulster County before returning to the Walkway Over the Hudson. It also includes an additional 18-mile Northern loop even deeper into the woods of Dutchess County toward the town of Clinton.

Elevation :  2,925 feet

Start time :  8:30AM – 9:30AM

The 75-mile routes starts out like the 55-mile, but includes an additional 20-mile northern loop through woods and farms.

Sunday morning Metro-North trains arrive after this route start time window has closed. Please make other travel arrangements from NYC.

Elevation :  4,196 feet

Start time :  8:00AM – 8:45AM

The 100-mile routes sets out like the 75-mile, but includes an additional 25-mile northern loop up through rolling hills to Elizaville.

Elevation :  5,822 feet

Start time : 7:30AM – 8:30AM

riding tour hudson valley

  • Cross the finish line and get your 2024 finisher medal and t-shirt, then head to the New Belgium Beer Garden for a free beer to celebrate! (Beer is for participants 21 and older only.)
  • Relax and recharge at the Finish Festival with live entertainment, photo ops, and activities for kids and the whole family, all while surrounded by the beautiful Hudson Valley greenery and spectacular views of the Hudson River.

All routes begin and end in Victor C. Waryas Park in Poughkeepsie, NY—right next to the Metro-North train station.

STAYING THE WEEKEND

Want to make a weekend out of it? Dutchess County Tourism has plenty of recommendations for where to stay  in the Poughkeepsie area.

There’s also plenty to do in the area (besides riding bikes). Dutchess County Tourism has you covered there, too!

Note that anyone riding the 100- or 75-mile route must either stay in the area the night before, or drive to Victor C. Waryas Park on the morning of the ride.  

Space for bikes is extremely limited, with only 44 bikes allowed on each train, and is available on a first-come, first-served basis at the conductor’s discretion. Please check current Metro North policy regarding bikes when making travel plans. There are no trains available for 100 and 75 miles riders on the morning of the ride.

Unlimited Biking offers a bike shuttle for Discover Hudson Valley Ride participants, even if you’re not renting a bike. For $49, you can have Unlimited Biking bring your bike to the Start at Victor C. Waryas Park and back again.

Drop-off will be at Unlimited Biking at 346 West 57th Street (Between 8th and 9th Avenue) on Saturday, June 24, between 9AM-5PM.

After the ride, simply drop your bike off with Unlimited Biking at the Finish, and they’ll take it back to the same location on Monday, June 26, for pick-up between 9AM-7PM. Bikes picked up after Monday will incur a $10/day charge.

Register for the bike shuttle

We recommend using Google Maps to plot your route. Enter Victor C. Waryas Park, Poughkeepsie, NY, 12601 as your final destination.

There are a number of public parking lots that are free on Sundays. Click here for a map of the area.

Go to Google Maps

WHEN YOU RENT A BIKE WITH UNLIMITED BIKING, THE OFFICIAL RENTAL PARTNER OF BIKE NEW YORK, PROCEEDS HELP FUND OUR BIKE EDUCATION PROGRAM!

Riders renting a bicycle with Unlimited Biking will pick up their bike at the Start and drop off their bike at the Finish. No need to transport your rental to and from the ride!

Photo Highlights

Feeling nostalgic? Check out the 2018 Discover Hudson Valley Ride video below.

If you would like to cover and/or ride the Discover Hudson Valley Ride as a member of the press, please complete and submit the following form.

  • First Name *
  • Last Name *
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  • What subject will you be covering? *
  • Please provide additional details: * *Required fields.
  • Name This field is for validation purposes and should be left unchanged.

Where and when does the ride start?

Discover Hudson Valley starts and finishes at Victor C. Waryas Park in Poughkeepsie, New York on Sunday, June 23, 2024.

Your start time depends on the distance you’ll be riding.

We strongly encourage you to start riding within the first 15 minutes of your route’s timeframe – the streets heading out of Waryas Park will be closed to vehicular traffic during the first 15 minutes of each start window to ensure your day starts smoothly.

Here are the start windows for each route:

  • 100 miles :   7:30AM – 8:30AM
  • 75 miles :   8:00AM – 8:45AM
  • 55 miles :   8:30AM – 9:30AM
  • 33 miles :   9:15AM – 10:15AM
  • 15 miles :  9:30AM – 10:15AM

Note : Timing is based on route support and rest area services. Once a start window has closed, participants will no longer have access to that route and must switch to a shorter option.

All riders must be on the route by 10:15AM. If you arrive after that time, we will not be able to provide your rider kit to you.

Can I rent a bike for the ride? Is there a bike shuttle again this year?

Yes! And now for the best part:  When you rent a bike with our official rental partner Unlimited Biking , proceeds help fund our bike education, community outreach, and advocacy programming.

You’ll pick up your bike at the Start and drop it off at the Finish; no need to transport your rental to and from the ride!

Unlimited Biking is also offering all registered riders the option of transporting their bicycle between NYC and Poughkeepsie. For $49 (round trip), Unlimited Biking will shuttle your bike to the Start/Finish area in Victor C. Waryas Park . After your ride, simply drop your bike off with Unlimited Biking for swift transport back down to the city. 

Check out rental and bike shuttle options .

What kind of bikes are permitted? Can I ride an e-bike?

We welcome any human-powered pedaled bike (road, mountain, fixed gear, recumbent, unicycle, tandem, tricycle, etc.). Due to updates in New York State law , pedal-assist e-bikes may be used on Discover Hudson Valley.

Throttle-powered e-bikes are not allowed on any Bike New York events.

How do I get to Poughkeepsie?

For driving directions, please enter Victor C. Waryas Park in Poughkeepsie, NY, into your GPS.

Trains from New York City are very limited on the morning of the ride. Participants riding in the 75- and 100-mile routes must make other travel arrangements from NYC as trains arrive after the start time windows for those routes have closed.

If you wish to have your bike transported to and from the city, Unlimited Biking is offering all registered riders the option of a bike shuttle service. For $49 (round trip), Unlimited Biking will shuttle your bike to the Start/Finish area in Victor C. Waryas Park. After your ride, simply drop your bike off with Unlimited Biking for swift transport back to the city.

Check out rental and bike shuttle options

Are breakfast and lunch included?

Breakfast starts at 7:00AM.

Lunch is not part of your entry for the 2024 Discover Hudson Valley Ride, but there are several restaurants just a few steps away from the Finish Festival.

When can I check in to get my rider kit? What is the latest I can get there on ride day?

Check-in is available on Saturday and Sunday.

Saturday, June 22 :  12:00PM – 4:00PM Location:  TBD

Sunday, June 23 :  7:00AM – 10:15AM (depending on your route distance ) Location :  Victor C. Waryas Park in Poughkeepsie, New York   

FOR ALL RIDER KIT PICKUP:

Bring your confirmation or final details email with QR code and your government-issued photo ID to receive your riding materials. Rider kits will not be provided to riders who are not present in person.

If you are checking in on the morning of the ride , we recommend you allow yourself at least 30 minutes prior to your preferred route’s start window to ensure you have ample opportunity to get through the check-in line, receive your cue sheet, use the restroom, and grab a complimentary breakfast. You should also account for travel time, parking, and potential lines when planning your trip.

Breakfast starts at 7:00AM on ride day.

Cue sheets will be distributed 10 minutes before the beginning of each start window. Starts are staggered to keep the ride flowing smoothly by spreading out cyclists along the route and minimizing our impact on local roads and communities.

Can I register on the day of the ride?

Yes, you may register in person. Details will be provided as we get closer to the event.

Please note : If you are registering on ride day, you must complete your registration before the start window for your route closes.

All riders must be on the route by 10:15AM.  If you arrive after that time, you will not be able to register for the ride.

What do I need to bring with me?

  • A   helmet : You gotta wear it. No ifs, ands, or buts.
  • A bell : New York State law requires that all cyclists have and use a bike bell.
  • Water bottle(s) : You’ll be able to fill your water bottle at the Start Area and every rest area.
  • Photo ID : so you can check in and get your cue sheet.
  • Cash/credit card: Cash payment is required for beverages at the beer garden, but you may use your card to grab some lunch at area restaurants, and use cash or your card to stock up on cool Bike New York gear!
  • A spare tube and patch kit : Bike repair along the routes is free, but there’s a charge for parts.
  • Sunscreen : Apply liberally and repeat.
  • Clothing : Wear jerseys, shorts, and arm skins with built-in sun protection, and a cap under your helmet to shield your head.
  • Hydrate, hydrate, hydrate : Check your water levels often and be sure to always have a full bottle on hand. Increase consumption of watery fruits and veggies in the days leading up to the ride. Sodium helps you hold onto fluids you’re drinking, so sip an electrolyte beverage during your ride. Drink little amounts often. Don’t wait until you’re thirsty; keep sipping from beginning to end. We provide snacks and hydration at all rest stops but, if you have dietary restrictions, please bring snacks that you can use to fuel your ride.
  • Travel light : There is no bag check, so bring only what you can carry with you on the ride.

Is the route closed to cars? Does the ride take place entirely on paved streets?

The route is open to traffic. Please visit New York State’s website for more information on the rules of the road .

The ride takes place almost entirely on paved streets, as well as the Walkway Over The Hudson and short segments of the Dutchess Rail Trail and the Hudson Valley Rail Trail. 

There are no dirt paths on the route, though there may be gravel surfaces at certain rest stops.

What is the elevation for each route?

15 mile – 895 feet

33 mile – 1,754 feet

55 mile – 2,925 feet

75 mile – 4,196 feet

100 mile – 5,822 feet

*All elevation gains are approximate.

Can I switch routes after I've started?

Yes. There will be points on each route at which you’ll have to decide whether to continue on your chosen route or switch to a different route. These splits are indicated on your cue sheet and will be marked with signs. Follow the signs for your chosen route.

Will the ride be canceled if it rains?

All Bike New York rides are rain or shine. In the event of severe or potentially dangerous weather, we’ll be in touch regarding contingency plans.

What's included in my registration fee?

Your registration fee covers: 

  • Entry to the ride
  • Breakfast at the start
  • Cue sheet (printed turn-by-turn directions)
  • GPS files for download
  • Access to services and amenities along the route (rest areas and SAG support)
  • Commemorative T-shirt
  • Finisher medal

I need to cancel my entry; what are my options?

Entries are non-refundable and non-deferrable, but you may transfer your entry to another person. Here’s how:

  • Log into  your EnMotive account .
  • On your account page, click on  Registrations on the left side and find your 2024 DISCOVER HUDSON VALLEY RIDE registration.
  • Click on the three dots.
  • Select  Transfer Registration .
  • Please enter the Enmotive account email address of the person to whom you would like to transfer your registration.
  • Click on  Transfer Registration ; this will send an email to that person notifying them of the transfer, with instructions on how to accept the transfer.
  • There is a $10 transfer fee to be paid by the transferee.
  • The transfer will only be valid for 48 hours , so be sure they accept quickly!

If you prefer to donate your registration fees to Bike New York (with our deep gratitide for your support), please email [email protected] to request that your registration fee be converted into a tax-deductible charitable donation.

If you purchased the EnMotive Protection Plan during registration and need to cancel your entry , please email [email protected] for assistance.

Are there age restrictions? Do I have to register my child?

Youth ages 3-17 are welcome to participate (provided they are registered) and ride with a parent or guardian, adhering to these guidelines:

  • Ages 3-9 must ride with an adult on a tandem bike, in a child’s seat on a tagalong bike, or in a bike trailer.
  • Ages 10-17 may ride their own bikes, but must remain in close proximity to the adult with whom they were registered.
  • Children under 3 are not allowed to participate in Bike New York events.

All participants, including children in child seats, on tagalongs, or in bike trailers, must be registered. Youth entries are available at a lower price.

How long will it take me to finish the ride?

That’s up to you! You can ride at your own pace and stop at rest areas for as long as you like, provided you remain in front of the SAG vehicles trailing the back of the pack. The Finish Festival closes at 5:00PM, so be mindful of your pace and ride accordingly.

Can I get the cue sheet ahead of time? Will GPS files be provided?

Cue sheets will be given out on the morning of the ride, 10 minutes before the beginning of the start time for each route. This allows us to ensure that people start the ride when rest areas are open and SAG vehicles are in position.

We will include GPS files in our final details email three days before the ride.

Will my ride be timed?

No, but you may use the timing feature in your GPS app to track your time.

Can I check my bag at the start? Are there any bag restrictions?

We don’t provide bag check for the ride; you must take your bag with you.

For our regional rides, there are no bag restrictions. Just make sure you can carry what you bring with you.

Does the beer garden accept credit cards?

No. Only cash will be accepted at the beer garden for purchasing beer and hard seltzer from our friends at New Belgium.

Where do proceeds from the ride go?

Bike New York is a 501(c)(3) nonprofit, and all proceeds from our events fund our free bike education, community outreach, and advocacy programs. In 2021 alone, we taught bike riding and bike safety skills to more than 30,000 kids and adults throughout New York City.

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I Took a Bike Tour Through New York's Hudson Valley — Here's Where I Found 'Farm-to-glass' Whiskey and the Best Meals

On a cycling vacation through upstate New York and the Connecticut countryside, discover a whole new side of the Hudson Valley you think you know.

When I think "bike tours," I tend to imagine winding my way up Tuscan hills or pedaling through sunflower fields in Provence, sharing the roads with grizzled farmers in ancient Fiats and Citröens. But as the pandemic shifted the attention of many travelers to overlooked destinations in their own backyards, so too did it force tour operators to get creative. Last year, DuVine, an international cycling company, unveiled a tour of the Hudson Valley.

The prospect didn't exactly thrill me. As a longtime resident of New York City who has spent countless weekends pawing through antiques, raiding farm stands, and agonizing over that perpetual question — Could I live here? — I thought I'd essentially checked the Hudson Valley box. That said, I am an avid cyclist — and a veteran of many two-wheeled holidays — so any bike trip pretty much has me at "bike." Add some of upstate's finest farm-to-table food (and, as I would find out, "field-to-glass" whiskey), a home base at the cozy lodge Troutbeck ( troutbeck.com ; doubles from $445) , and the general fellowship of the people who typically choose to take bike tours, and, well, I could hardly say no.

On a simmering summer morning, I arrived solo to join a group of five couples assembled on the lawn at the culturally significant Troutbeck — over the last two centuries, guests have included Henry David Thoreau, Theodore Roosevelt, and Thurgood Marshall. The hotel occupies a 250-acre stretch in Amenia, New York, a hamlet near the border with Connecticut. My fellow cyclists had come farther than I had, hailing from Maryland, Virginia, Georgia, and even Mexico. One couple had e-bikes, the great equalizers — despite being in their 70s, they had no trouble matching the most energetic riders. We were led on the road by our guide, Ross Eustis, a New Yorker who'd gone to boarding school in the area; for him, passing a rival school where he'd played baseball was a literal trip down memory lane.

Just as the first motorists had the lobbying efforts of 19th-century cyclists to thank for the good roads they drove on, the contemporary cyclist can often give thanks to the railroad industry for creating some of the country's best biking infrastructure. The 26-mile Harlem Valley Rail Trail — which runs from Wassaic to Copake Falls and can be picked up near Troutbeck — featured often in our daily cycling plan. The trail provided a level, shaded, and traffic-free artery to places like Millerton, a tiny town that punches above its weight, with artisanal tea producer Harney & Sons ( harney.com ) ; the Edward Hopperesque Oakhurst Diner ( oakhurst-diner.com ; entrées $13–$25) ; coffee roaster Irving Farm ( irvingfarm.com ) , where we stopped to refuel; and Westerlind ( westerlindoutdoor.com ) , a sort of hipster Woolworths.

When not on the rail trail, we traversed green and rolling back roads, crisscrossing the state border, past fields of thigh-high corn, gushing waterfalls, and tidy Dutch-style houses. We took refuge from the heat at places like McEnroe Organic Farm ( mcenroeorganicfarm.com ) , which has its own market and dining operation, and quenched our collective thirst with tastings of Kings Highway Fine Cider ( cider.nyc ) , a zero-added-sugar drink produced by onetime journalist Tyler Graham, who started out making cider in his Brooklyn apartment.

One afternoon we were joined by chef Gabe McMackin, an enthusiastic cyclist and former Brooklynite who closed his Michelin-starred restaurant, the Finch, in 2020; now he helms the food and beverage program at Troutbeck. He pointed out secret swimming holes and favorite pizza spots — like the Lantern Inn ( wassaiclanterninn.com ; entrées $15–$20) , in Wassaic. When he suddenly realized his own dinner service was looming, I agreed to bike back with him. After riding at a blistering pace, I collapsed in a hammock. He headed straight to the kitchen. But our group's meal that night was actually at Serevan ( serevan.com ; entrées $32–$38) , a regional staple founded by chef Serge Madikians, a self-described "Armenian from Iran" whose exquisite menu includes saffron-infused spaetzle, rack of lamb with herbed labne , and eggplant stew. Madikians is also a pilot; he's been known to ferry fresh seafood from Cape Cod in time for dinner.

The next day, the remnants of Tropical Storm Elsa began to whip through the valley, and we rode past power crews repairing downed lines. After a lunch stop — we stayed mostly dry under the porch roof of a delicatessen — we climbed into the support van for the short drive to Hillrock Estate Distillery ( hillrockdistillery.com ) , which is housed in a home built by a Revolutionary War captain.

Hillrock was originally overseen by legendary distiller David Pickerell (he helped bring Maker's Mark to prominence) and still practices "floor malting" — laying out the barley in a Zen-garden-like spiral on a cold stone floor to let it germinate. My group retreated to a cozy room where five whiskeys were arrayed in front of each of us. After tasting fiery rye, smoky and sinuous single malt, and oaky-sweet bourbon, a few of us elected to return to Troutbeck by bike. There was a consistent drizzle, but we were warm, and there were still more country roads to be explored.

A version of this story first appeared in the June 2022 issue of Travel + Leisure under the headline Back in the Saddle.

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Preparing for the Tour

CTHV---preparing---header.jpg

B elow is a link to a useful list of what to pack for the ride, as well as information on choosing a bike, accessories and proper clothing. Please note: Use of an CPSC or Snell approved helmet is required.

You’ll also find helpful tips on training, to get in shape for the 30-50 miles each day. While this is not a strenuous trek, it is much more enjoyable if you are conditioned to handle the distance each day.

Training for the Ride

To prepare for the Cycle the Hudson Valley Bike Tour, there is no substitute for miles and minutes. People who spend time conditioning themselves have the most fun. Waiting until the last minute to train your body and tune up your bike usually means you’ll find the daily ride hard enough that you won't have the energy to enjoy the historical sites and evening activities.

Training is especially recommended for families with children.

A 10-year- old simply won’t be ready without some practice rides. Set a reasonable goal given your schedule, and stick to it. The work will pay off. Beforehand, you might participate in an organized tour to get used to traveling by bike with a group, or, consider joining your local bicycling club. Again, you'll meet great people who can help you train and give tips on touring.

Basic Training Schedule

APRIL: The plan is simple: ride five miles. This should take less than an hour. Start taking five-mile rides in April. By making several short rides at this time of year, you can build up gradually. Once you are comfortable riding five miles, do it twice in a row.

MAY: Begin with ten mile rides for the first couple of weeks, then gradually add one five- mile ride at a time. By the end of May, you should be able to put together four or five five-mile rides, doing 20 or 25 miles at a time. The weather is great, so you'll want to be outside anyway.

JUNE & JULY: Move up to 30-35 mile rides. Then, a week or two before Cycle the Hudson Valley, go for it. Try to complete at least two 50-mile rides, Cycle the Hudson Valley style. This means 2 days back-to-back, be sure to stop frequently, incorporate some sightseeing, and pace yourself to have the energy to enjoy the rest of the day.

Training with Children

It is critical that children train for the tour, too. They need to be reminded to drink often. They also need to learn when to eat and proper road etiquette. Practice helps them ride in a straight line and obey traffic laws. These are crucial safety skills—not just for the tour, but every day. It is also important to find out how children handle riding in a trailer. No one wants to discover on the first day, 30 miles from the start, that your child cannot tolerate the motion. See “Riding Safely In Groups” for additional information.

Riding Safely in Groups

Tips from the Tom the Safety Guy on how to ride safely in groups---- including riding with children

1--- Ride Predictably

Ride in a straight line---no weaving or swerving

No riding with both hands off the handlebars

No sudden stops without saying “Braking or Slowing”

Get off the path BEFORE you stop

2--- Let them Know where You are Going to Go

Use audible and hand signals-for braking, turning, and passing

3--— Wait Your Turn

Don’t bunch up---especially at stops

Most collisions occur during the first few feet of starting up

4— A Family that Bikes Together—Stays Together

Anyone 17 and under must be riding and under the supervision of their adult

Choosing Your Bicycle

Everyone knows that higher quality, lighter weight bicycles ride more easily and are less likely to break down, during the ride. And easier riding translates into a more energized rider by the end of the day. A light bike is not the only solution, however. Having a wide selection of gears will also make your journey more pleasant. Additionally, if you have a strait handle bar you might find that Bar Ends can add a great deal of comfort by offering alternate hand positions. Finally, a bicycle sized to your body is crucial for safety and comfort. Bicycle shops can best fit you to the appropriate size. But if you don’t have the budget for a new bike, don’t despair. Every year, people complete the tour on bicycles of all kinds. Just be sure to get your bike top in mechanical condition before the ride and do some training.

Important Bike Accessories

HELMET: The most important accessory is a good helmet. And they are increasingly affordable. Find one that fits well and has been certified by the Snell Institute and passes CPSC (Consumer Product Safety Commission) standards. Helmets are MANDATORY for the Cycling the Hudson Valley bike tour, but you should wear it every time you ride. This is especially true if you are setting an example for children.

A FRAME PUMP, PATCH KIT, TIRE TOOLS and A SPARE TUBE: Don't know how to change a flat tire? Don't worry – most people don’t. Just visit your local bike shop on a weekday morning (when they aren't busy) and ask them to show you. Or, call the local bike club and ask for help. While we're talking about repairs, bringing a spare DERAILLEUR HANGER can be a great idea. Derailleur hangers are very bike specific, and because there is such variety in the fit of derailleur hangers there’s a strong probability that not every shop along the trail will have exactly yours in stock. In the event that yours breaks, your ride could be done until you find a replacement. The good news is that they're cheap insurance, and easy to pack. Go to your local bike store before the tour & order the one specifically for your bike, probably $30 or less. Pack it in your suitcase, so that if you need it on the tour our mechanics will be able to get you ready to roll again.

OTHER TOOLS: Many riders bring along a chain tool, spoke wrench, adjustable wrench, Allen wrenches (metric, 4, 5, and 6 mm), and duct tape. Even if you're not sure how to use these handy items, someone on Cycling the Hudson Valley will be able to help.

BAG: You'll need a place to carry repair items, along with money, glasses, sun block, and food. A belt bag or fanny pack work well, as do the variety of bicycle-mounted bags. Remember: you won't be have access to your luggage until the end of the day, so you may also want rain gear or a windbreaker.

WATER: Water bottle cages and multiple water bottles are key. Nothing stops you faster than dehydration. Be sure that your water bottle is easy to open so that you'll drink often. Many knapsack style hydration systems include a bladder for water and provide extra storage space to carry the items listed above. Find the system that works best for you. That's another benefit of training rides; you can test out the accessories that you plan to bring on Cycle The Hudson Valley.

For an entire week, the full weight of your body is going to be pressing down on three places where your body meets your bike: hands, feet and posterior. Proper clothing can make a huge difference, when it comes to your comfort.

Gloves help with pressure and chafing. Consider a washable style.

Shoes come in many styles, from “ski-binding” styles that attach to the pedal, to a “sneaker” touring shoe. Touring shoes work better for all the sightseeing you will do off the bike.

Shorts: Bicycling shorts help combat the rider’s biggest enemies: heat and moisture. Sitting on a bicycle seat all day creates an ideal microclimate for bacteria growth, which quickly leads to a sore posterior. Cycling shorts have a sewn-in pad to soften contact and absorb moisture. Good pads dry quickly and Lycra fabric also allows perspiration to dry quickly, keeping you cooler. By conforming to your skin, shorts are more aerodynamic as well. If you don't like Lycra, however, consider touring shorts. These have the appearance of normal shorts, but are constructed with a pad, and are sewn so that seams don't overlap in any sensitive areas. No matter what type of shorts you use, applying diaper cream to the contact areas before riding can help avoid problems.

Shirts : While people wear all kinds of jerseys, you can cycle in anything on a dry summer day. In cool or damp conditions, some wicking materials are preferred. New performance materials keep you warm even in wet and cold conditions – both of which are possible during Cycling the Hudosn Valley. Always carry a raincoat or poncho on your bike.

A good rule of thumb: drink before you're thirsty! This rule applies no matter what the weather. Some people claim they don't perspire while cycling, but the truth is, you are creating a 10-20 mile-per-hour wind across your skin. You may be sweating, but the wind dries it almost immediately. This fools people into thinking they aren't sweating and they don't drink adequate water. Worst case scenario, they face heat exhaustion, followed by heat stroke. More often though, these riders stagger on, wondering why they feel terrible, and why the biking seems so hard. If they would just stop and drink a quart of water, they would be amazed at how much better they feel.

A common mistake is under eating or eating at the wrong times. On the tour, expect to burn an extra 10,000+ calories. If you skip a meal, your body will run out of fuel and start burning fat reserves. This sounds good, but when your body shifts to burning fat, riders suffer what is known as "the bonk." This isn't just normal fatigue. It is like falling into an emotional chasm, with depression, anxiety and plenty of tears. After a few fig bars, however, their entire personality can change. It is common for those that "bonk" to be crying, unable to even lift their arms. But an hour later, after a good meal, they are leading a pace line at 20 miles per hour.

We look forward to you joining us for the Cycle the Hudson Valley Bike Tour. Take the time to train, because conditioned riders are happy riders—the kind we like to travel with. See you in July!

For even more packing and preparation tips, check out long time tour volunteer Buzz Gamble's 20 Tips to Make the Most of Your Bicycle Tour.

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riding tour hudson valley

Whether you ideal day includes a leisurely outing on a rail trail, a roadside ride through prsitine farmland or a mountain biking adventure, Dutchess County has it all.  Be inspired by the beauty of the Hudson River Valley landscape atop one, two, three or more wheels!

Dutchess is fully equipped for your cycling needs.  Find several bike rental, repair and equipment shops.  Plan ahead with this list of bicycle parking locations throughout the county.

Then take your bike for a spin on one of our trails such as the Walkway Over the Hudson State Historic Park, the William R. Steinhaus Dutchess Rail Trail, or Harlem Valley Rail Trail showcasing the finest landscapes in upstate New York.

riding tour hudson valley

Download our new Bike Tour Guide!

riding tour hudson valley

Check out the Empire State Trail, which is a 750-mile path connecting people to New York’s spectacular natural beauty, cultural heritage, iconic landscapes and unparalleled outdoor recreation opportunities. The trail connects urban centers, village main streets and rural communities from New York City through the Hudson River Valley, west to Buffalo along the historic Erie Canal, and north to the Adirondacks. For more information, visit empiretrail.ny.gov .

riding tour hudson valley

Bike Tours of Dutchess County

Six self-guided bike tours with directions and maps of routes throughout Dutchess County, including routes to accommodate different ability levels, elevations, and distances. Choose to ride on dedic...

riding tour hudson valley

Bikeway Inc.

An optimal spot for any, and all, biking needs and resources. They provide bike rentals, repairs, local rides and clubs, used bikes, sales and accessories. As of June 9, 2022, Bikeway offers bike ren...

riding tour hudson valley

City Bike Rentals of Poughkeepsie

Find a variety of bike rental options conveniently located near the Walkway Over the Hudson and Dutchess Rail Trail at City Bike Rentals of Poughkeepsie. Explore Poughkeepsie with bike rental options ...

riding tour hudson valley

Cold Spring Bike Rental & Tours

Explore the scenic side of Dutchess with Cold Spring Bike Rental and Tours located in Scenic Hudson's Long Dock Park in Beacon. These trail adventures are great for all ages and experience levels. Off...

riding tour hudson valley

Gotham Bicycle Tours

Safe, fun weekend bike tours on the Empire State Trail that are great for all abilities. All tours include vehicle support and rest stops. Discount Metro-North Getaway packages are available from Gran...

riding tour hudson valley

Great Freedom Adventures

Six day bike tours (July and October) showcasing the natural and cultural richness of the scenic Hudson Valley. Tours feature pastoral cycling, mansions, historic sites, wineries, gardens, a river cru...

riding tour hudson valley

Harlem Valley Rail Ride

Fully-supported bike ride along beautiful, low-traffic country roads. Choose from 23, 33, 45, 57,72, 80 and 2-different century routes which include a 6 mile stretch of the car-free Harlem Valley R...

riding tour hudson valley

Harlem Valley Rail Trail

26 miles of scenic paved walking, rollerblading, biking and cross-country skiing trails, linking towns, villages and state parks on the rail bed from the Wassaic Metro North Station to Hillsdale. No h...

riding tour hudson valley

Hopewell Depot

This southern trail head of the Dutchess County Rail Trail in the village of Hopewell Junction includes the restored 1873 railroad station at the Hopewell Depot Museum. The museum visitor center provi...

riding tour hudson valley

Maybrook Trail

This 15-mile paved stretch of the Empire State Trail runs from Pawling (parking at 239 Route 292 in the Hamlet of Holmes) to Hopewell Depot (parking at 36 Railroad Avenue in Hopewell Junction) and cro...

riding tour hudson valley

Peoples Bicycle

Bike Rentals summer through October.Saturday and Sundays hours 10am -6 pm .Rates are $25.00 -$50.00 a day depending type of bike. We're an everyday bike shop. Whatever your needs are, pop in and ...

PV Bicycle Shop

Repairs, large selection of new and used bikes. Accessories for beginners and pros. Local Places to ride....

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Gotham Bicycle Tours

Hudson Valley Farm-to-Table Bike Tour

The best of food, wine and spirits along the Empire State Trail in the Hudson Valley

The perfect day out for private groups of up to 8 people

PRIVATE TOURS ONLY – Tour price starting at $900 per group (not per person)

This ride has it all:  beautiful scenery mixed with delicious locally produced Hudson Valley wine, spirits and food. This bike ride packs a lot of highlights into a great 30-mile itinerary that is perfect for all abilities and includes off-road bike paths and quiet back roads with up to 5 food and beverage related stops. 

This bike tour has spectacular scenery as you ride along the flat Wallkill River Valley with a view of the majestic Shawgunk Ridge off in the distance. Our staff will meet your group in Gardiner, NY where there is plenty of free parking. We can also shuttle your group over from the Poughkeepsie train station if you are coming from NYC. We’ll send you on your way with GPS navigation and plenty of snacks and beverages as you ride through a fertile valley that is home to a number of wineries, micro-distilleries and farm-to-table restaurants. You can stop and any – or all – of 5 stops. Our support vehicle will meet you at each of them and you can store any products you buy at each stop in the vehicle along with any personal items you do not want to carry while you ride.

Stops include:

  • Mile 11.5 – Rail Trail Cafe in Rosendale – Farm to table food served in 100% outdoor setting next to a bike path
  • Mile 18.5  – Coppersea Distilling – Whisky distillery offering outdoor tastings and whisky slushies
  • Mile 26 – Robibero Family Vineyards – Outdoor wine tastings
  • Mile 28 – Tuthilltown Spirits – Distillery specializing in a variety of spirits including whisky, gin and vodka
  • Mile 30 – Whitecliff Vineyard – Outdoor wine tastings or wine by the glass. 

After reaching Whitecliff Vineyard, it is a 2.5 mile ride back (uphill) to the parking lot where the ride started. But we can shuttle anyone from your group who does not want to do this ride. Or we can give you a ride back to the train. 

Have any questions? Email lukas@gothambiketours.com for the answers!

riding tour hudson valley

Thank you both for an amazing trip! The ride was beautiful, and at just the right intensity (challenging, yet doable). Your organization and planning were spectacular…it couldn’t have been a better experience!

Upcoming Bike Tours

  • Empire State Trail Vacation Tour
  • Hudson Valley Craft Brewery Bike Tour
  • Empire State Trail Day Tour
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4 Day Hudson Valley Inn to Inn Bike Tour

Join us on a journey through the Hudson Valley National Heritage Area.  Ride 135 miles over four days on the various rail trails that comprise the Empire Trail network through southern New York State.  We’ll experience historical landmarks like the Rosendale Trestle, Walkway Over the Hudson, and Kensico Dam along the way.  Spend three nights in scenic Hudson Valley towns and enjoy the Tarrytown Castle Inn (it really is a castle)!

riding tour hudson valley

The Hudson Valley itinerary has been specifically designed to prioritize portions of the Empire Trail that are paved or crushed gravel trail and not roadshare.

HUDSON VALLEY INN TO INN TOUR SUMMARY

Day 1 – 27 miles:  Meet us in Tarrytown at 10am and we’ll shuttle you to Kingston.  There you will start your 27 mile ride to New Paltz.  View the remnants of the Rosendale Cement Factory kilns and experience the Rosendale Trestle as you bike right to the hotel.  Enjoy views of the Shawangunk Mountains (“The Gunks”) and take time to experience the outdoorsy trail town of New Paltz.

Day 2 – 36 miles:  On day 2 we’ll tackle 36 miles of riding with some hills along the way.  Don’t worry though, the entire day is paved trail!  In the morning we’ll ride the Walkway Over the Hudson. Then in the afternoon, we’ll experience the Maybrook Section of the Empire Trail.  This section takes you through remote dense woods with lakes and beautiful wetlands!  We’ll end the day with a shuttle to Beacon, a historic town right on the Hudson River.

Day 3 – 45 miles:  After breakfast, we’ll get back to the trail.  Spend your day riding 45 miles through small trail hamlets like Mahopac and Yorktown Heights.  Lunch is on your own today with plenty of small businesses to support along the way.  We’ll end our longest day of riding with a group dinner in Tarrytown! Then spend the night at the Castle Inn and Spa, a single family home from the 1900s converted to a one of a kind inn.

Day 4 – 27 miles:  On our final day of riding we’ll spend half of it on the Empire State Trail. Then we’ll leave that trail system behind and finish on the Bronx River Pathway.  This 12 mile scenic section will allow us to avoid major road sections around NYC and prioritize our time on trail.  Our Hudson Valley bike tour ends at the expansive Kensico Dam on the National Register of Historic Places.  We’ll allow time for you to explore the area while we have a picnic lunch.  Once finished, we’ll pack up and shuttle you back to your car.

For a 4-day Hudson Valley bike tour detailed itinerary, please call 570.325.8430 and ask for Sierra OR send an email to [email protected]

Hudson Valley Dates:

  • 28th – 31st  (sold out,  join the waitlist )
  • 18th – 21st (sold out,  join the waitlist )
  • 6th – 9th (sold out,  join the waitlist )

If the date you are interested in is currently sold out, please  click here to join our waitlist!

  • Difficulty:  Easy/Moderate – Crushed gravel and paved trails, some hills on days 2 and 3
  • Trip Size:  Up to 12 guests, 2 guides
  • Minimum Age:  13 years old

There is a $250 non-refundable deposit, per rider, required at the time of your reservation.

  • Conventional bikes and eBikes only;  NO trikes, recumbents, or tandems. 
  • E-bike rentals are available for an additional charge
  • For a detailed itinerary and FAQ, please call 570.325.8430 and ask for Sierra OR send an email to [email protected]
  • CLICK HERE to view our special 4-Day Hudson Valley, 4-day D&L & 6-Day Erie Canal inn to inn bike tour brochure.

Hudson Valley Rates:

(Special 2024 Introductory Pricing)

  • Individual with own bike  – $1199.
  • Bike rental (if needed)  – $119.
  • e-Bike rental (if needed)  – $239.
  • Single supplement  – $299. additional for those traveling solo

RATE INCLUDES

  • Biking on 135 miles of rail trail
  • Overnight accommodations at the Hampton Inn, The Roundhouse, Castle Inn & Spa
  • Professional bike guides
  • Basic bike repair
  • Replacement bikes if needed to complete the ride
  • Rest stops with snacks and water
  • Breakfast on 3 days
  • Lunch on 3 days
  • Dinner on 1 day
  • Luggage transportation to each accommodation
  • Morning trail briefings
  • Transportation back to your car by 2pm on the final day
  • Entire trip is fully supported

RESERVATIONS & INFORMATION

For more information on our fully supported, four day inn to inn bike ride, please give us a call at 570.325.8430 and ask for Sierra. Or, you can send us a request via email to [email protected]

Note: If the date you are interested in is currently sold out, please  click here to join our waitlist!

Randonnee Tours

Hudson Valley Biking 4 Days

  • Accommodations
  • Hudson Valley
  • Short Escape

Travel & Leisure recently named the Hudson Valley as one of the most exciting places to travel in 2021. With its thriving locavore movement of boutique farms and orchards, charming villages, historic properties and quiet rural roads, the appeal is evident. This 4 day, 3 night escape provides an itinerary from the wonderful Troutbeck, just outside of Amenia, NY.

Troutbeck, Leedsville Road, Amenia, New York, USA

Day 1+2+3+4

What’s Included in the Cost of Your Trip?

INCLUDED IN REGULAR TRIP

3 nights lodging All breakfasts and 1 dinner Luggage transfers Detailed GPS instructions and maps Personal meet & greet with our local Area Manager Area Manager available throughout the tour

ARRIVE / DEPART

ACTIVITY LEVEL

Land Cost: US $1,950 pp Single supplement: US $475

Bike Rentals

Hybrid or Racing Bikes: US$180

E-Bikes: US$240

E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide.  E-bike rentals are non-refundable.   

After arriving to the hotel, settle in and then head out cycling. The first day’s route follows the flat & paved Harlem Valley Rail Trail to the village of Millerton. Voted one of America’s Favorite Small Towns, stop in at Irving Farm for a fresh roasted coffee and then visit any one of the many art galleries and antique stores. On the return route, stop in at an organic farm market and sample organically raised fruit and vegetables, or some of the owners pickled, baked, jammed, stewed and simmered bounty. Arriving back to the hotel, relax and enjoy dinner in the delightful dining room.

Ride distance: 20mi (32km); elevation gain 1,000’ (340m).

Housatonic Valley

Today, ride across the border into Connecticut and the Housatonic River Valley. Near a trailhead for the Appalachian Trail, cross a historic covered bridge built in 1842 and now a National Historic Monument. Pass historic barns on quiet secondary roads to Kent, a charming village with great restaurant options for lunch before riding back to Troutbeck. You’ll probably want to dine out on at least one of the nights you are here and we have just the place to recommend, in nearby Amenia.

Ride distance: 36mi (60km); elevation gain 2,700’ (900m).

Ride north today discovering more of the region. In the early 1800’s, New York produced more than half the nation’s barley and rye and the Hudson Valley was the country’s breadbasket. With abundant high quality grain, local craft spirits flourished and over 1000 farm distilleries produced whiskey and gin reflecting the unique terroir of the region. In the 1930’s, Prohibition forced these distilleries to shut their doors but there has been a resurgence in this craft. Enjoy a behind-the-scene tour of one of the premier distilleries and taste award-winning whiskeys, or save that for when you are back to the hotel.

Ride distance: 42mi (72km); elevation gain 2,700’ (910m).

There is time for one last ride, to the village of Rhinebeck, settled by the Dutch in the 1680’s. Peek in the Beekman Arms which has operated continuously since 1766, retaining much of its colonial charm and character. Check out the Antique Market, a multi-dealer antique emporium that is located behind the hotel in a classic 2 story barn. Enjoy lunch and then shuttle back to the Troutbeck to depart.

Ride distance: 30mi (50km); elevation gain 1,950’ (650m).

riding tour hudson valley

This property is a historic country inn that began as a private estate built in 1765 by a prominent New York family who played host to Mark Twain, Ralph Waldo Emmerson, and Henry David Thoreau, among others. The property sits on 250 acres with comfortable guest rooms, library, stunning outdoor swimming pool, two US Open-surface tennis courts, formal gardens and an impressive farm-to-table restaurant.

riding tour hudson valley

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  2. Hudson Valley Bike Tour

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  3. Horseback Riding in the Hudson Valley

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  4. All-Inclusive Senior Group Tours in the Historic Hudson Valley

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  6. Hudson Valley Bike Tours

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VIDEO

  1. Exploring trail by the Hudson River on @Onewheel and Ebikes

  2. 2024 Tour Hudson Valley

COMMENTS

  1. THE 5 BEST Hudson River Valley Horseback Riding Tours (2024)

    THE 5 BEST Horseback Riding Tours in Hudson River Valley, NY. 1. Westchester Trail Rides. Our guide, Dylan, took great care with my preteen/teen beginning riders, and led us on a lovely ride through the woods. 2. Mohonk Mountain House Hudson Valley Day Trips. 3. Ivy Rock Farms.

  2. An Equestrian's Guide to Horseback Riding in the Hudson Valley

    4 Hudson Valley Rail Trail, 101 New Paltz Road, HVRT Pavilion, Highland Beginning in Highland and ending in New Paltz, this 3.6-mile, gently sloped asphalt trail spans the distance between Walkway Over the Hudson State Historic Park and Tony Williams Park, which means it will lead you to a destination as scenic as the one from which you embarked.

  3. 15 Places to Learn to Ride a Horse in the Hudson Valley

    Horseback Riding Facilities in the Hudson Valley. Mohonk Stables - High Falls 845 256-2784. Juckas Stables - Pine Bush 845 361 1429. Lucky C Stables - New Paltz 845 255 3220. Gardnertown Farms - Newburgh 845 564 6658. Crosswinds Equestrian Center - Lagrangeville 845 223 7433. Ashokan Horseback Riding Club - Olivebridge: 845 657 8021.

  4. Mountain Valley Farm

    Horseback Riding Adventures at Mountain Valley Farm - Millerton, New York. With access to more than 4000 acres of trails with sweeping vistas along the Hudson Valley and the Berkshires. Whether you are a casual rider looking for horseback riding adventures, trail riding, round pen lessons or even skeet shooting, our services are available to you.

  5. Saddle up at the Hudson Valley's Horseback Riding Farms and Stables

    Pond View Farm, Lagrangeville. Pond View Farm is an English riding school that offers non-competitive riding for children of all ages and abilities. The farm is part of the Arlington School District's summer camp program. Throughout the 30 acres of breathtaking views, there are 10 miles worth of trails and facilities.

  6. 2 Hour Trail Ride

    Come horseback riding in the beautiful Hudson Valley with an experienced guide to show you the way! With 117 acres of breathtaking farmland and trails, Juckas Stables rides are fun for the whole family! Book Now Learn More $ 160. Year-Round; 75 minutes; 75 Minute Trail Ride.

  7. 45 Minute Trail Ride

    Duration: 45 minute. Schedule: Daily (some days require call-to-book) Time: If you don't find the time you wanted on our schedule please call to book (845)-361-1429. Ages: 7+. Weight Limit: 250 lbs, For the safety of yourself, the group and our horses, please put an accurate, current weight. Experience: No prior riding experience necessary.

  8. All-Inclusive Senior Group Tours in the Historic Hudson Valley

    Contact Nikki, Group Sales Representative. (800) 647-2624 Ext 1031 | [email protected]. During your Senior Group Trip, you'll experience the best of every season in the Hudson Valley without leaving the Resort at Rocking Horse Ranch!

  9. Best places to ride a horse in the Hudson Valley

    Hollow Hill Farm, LLC. 87 Hill Ave., Montgomery. 845-978-8151. Small horseback riding & boarding facility located in Orange County NY. Family owned and run we teach the fundamentals of riding from the ground up creating a safe, fun & educational riding experience. We also offer top quality care for your horse!

  10. New York's Training and Trail Riding in Hudson Valley

    Dates: Open all year. Rates: Daily - $570.00 USD includes 3-4 hours of lessons/hacking. Hunting can be arranged from Aug-Dec. 26 with Millbrook, Old Chatham and Windy Hollow hunts. And from January-March in South Carolina and Georgia. Formal attire required. Cap Fees range from $100.00-$250.00 USD.

  11. Horseback Riding at Schunnemunk Shadow Stables

    Home to Schunnemunk Shadow Stables and Hollybush Classical Dressage Center. Our two locations are located less than a mile from one another and are mirror operations. We are a full service boarding facility and offer training and horseback riding lessons daily. Located in scenic Mid-Hudson Valley, NY, our relaxed, family atmosphere offers ...

  12. Discover Hudson Valley Ride

    The Routes. All routes begin and end in Victor C. Waryas Park in Poughkeepsie, NY—right next to the Metro-North train station.. NEW FOR THIS YEAR: The Walkway Over the Hudson and the Hudson Valley Rail Trail will be open to Discover Hudson riders only!. We strongly encourage you to start riding within the first 15 minutes of your route's timeframe - the streets heading out of Waryas Park ...

  13. 8 Terrific Tours to Explore the Hudson Valley's Hidden Corners

    - Curated Tours - Westchester residents Robin Helman and Elizabeth Knell launched Go Love NY in fall 2019 to curate private and small-group Hudson Valley excursions, with a focus on food, nature, and culture. The offerings change, but expect experiences like kayaking to Bannerman Castle, a private tour and happy hour at Russel Wright's Manitoga House in Garrison, visits to local alpaca ...

  14. Riding the South and North County Trailway

    May 18, 2020 / in Hudson Valley, Rail Trails /. If there is one bike path that most closely resembles a trunk-line, main artery for bikes in the Hudson Valley region, it is the South and North County Trailway in Westchester County. This trail, which runs continuously from Bronx/Yonkers border for almost 50 miles to the Village of Brewster in ...

  15. I Took a Bike Tour Through New York's Hudson Valley

    Last year, DuVine, an international cycling company, unveiled a tour of the Hudson Valley. ... After riding at a blistering pace, I collapsed in a hammock. He headed straight to the kitchen.

  16. Parks & Trails New York :: Preparing for the Tour

    To prepare for the Cycle the Hudson Valley Bike Tour, there is no substitute for miles and minutes. People who spend time conditioning themselves have the most fun. ... Once you are comfortable riding five miles, do it twice in a row. MAY: Begin with ten mile rides for the first couple of weeks, then gradually add one five- mile ride at a time ...

  17. Biking

    Biking in the Hudson Valley. Whether you ideal day includes a leisurely outing on a rail trail, a roadside ride through prsitine farmland or a mountain biking adventure, Dutchess County has it all. Be inspired by the beauty of the Hudson River Valley landscape atop one, two, three or more wheels! Dutchess is fully equipped for your cycling needs.

  18. 21+ Hudson Valley Day Trips Worth Taking Now!

    February 26, 2022. 21+ Hudson Valley Day Trips. Worth Taking Now! Trees, Mountains, the Hudson River, small towns and bustling cities. Welcome to the Hudson Valley, a mix of old and new, history and art. Because of all these things, it's very easy to plan Hudson Valley Day Trips several times a year. There is so much to do in the Hudson ...

  19. How To Bike The Hudson Valley Greenway Trail In Four Days

    Hudson Valley Bike Tour Itinerary. For a 4-day, three-night trip it is recommended that you ride roughly 50 miles a day, specific mileage will be outlined in the itinerary described below. Much of your 4-day trip will be on Rail Trail sections of the Hudson Valley Greenway. Rail Trails are disused railways converted into multi-use paths.

  20. 11 Hudson Valley Road Trips With Magnificent Views

    Dutchess County Harlem Valley. Where: Pawling to Wassaic via Route 22 18.7 miles Best foliage views: Along the Appalachian Trail and Swamp River, peak is early November Why it's great: "The entire stretch of Route 22 north from Pawling toward Millerton and beyond is a fantastic drive year-round. This route is nestled in the Harlem Valley, with beautiful views of farms such as the Harlem ...

  21. Hudson Valley Farm-to-Table Bike Tour

    The perfect day out for private groups of up to 8 people. PRIVATE TOURS ONLY - Tour price starting at $900 per group (not per person) This ride has it all: beautiful scenery mixed with delicious locally produced Hudson Valley wine, spirits and food. This bike ride packs a lot of highlights into a great 30-mile itinerary that is perfect for ...

  22. 4 Day Hudson Valley Bike Tour

    Day 2 - 36 miles: On day 2 we'll tackle 36 miles of riding with some hills along the way. Don't worry though, the entire day is paved trail! ... For a 4-day Hudson Valley bike tour detailed itinerary, please call 570.325.8430 and ask for Sierra OR send an email to [email protected]. Hudson Valley Dates: July .

  23. Hudson Valley Biking 4 Days

    Land Cost: US $1,950 pp. Single supplement: US $475. Bike Rentals. Hybrid or Racing Bikes: US$180. E-Bikes: US$240. E-bikes are generally available but are on an 'on request basis ' and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and ...