self walking tour of portland maine

16 Awesome Walking Tours in Portland, Maine

Portland, Maine is a beautiful city that’s perfect for taking a walking tour. With its historic architecture, coastal views, and delicious fine dining restaurants , diners , and cafes, there are plenty of sights to take in.

It also happens to be Maine’s largest city, so you get all the energy of a city without all the crowds (well, some places can be kind of crowded).

From a cultural exploration of the city to a jaunt along the waterfront in Old Port, each of the walking tours offers something unique. Whether you’re looking for a leisurely walk around town or an in-depth look at local history and culture, there are tours to suit all interests.

You can choose from a variety of walking tours, including learning about Portland’s cool history , a culinary journey through some of the best eateries in town, or even a craft beer tour .

Whether you’re an architecture buff, a foodie, or just looking for some fresh air and exercise, there’s something for everyone on these fun Portland Maine walking tours.

If you know you are coming to Portland but aren’t sure where to stay, why not opt for a place with an indoor pool? Here are the top-rated hotels in Portland that have indoor pools .

No matter which tour you choose, you can be sure to get an unforgettable experience while exploring the best of Portland Maine on foot. So lace up your shoes, grab your camera or phone, and get ready to experience a wonderful walking tour of the city!

Walking Tours Portland Maine

✅ Walking Tours: Portland, Maine’s History

Exploring the history of Portland, Maine is a great way to really get to know this vibrant city. For those looking for an in-depth look into the past, guided walking tours offer a unique opportunity to explore the historic sites, culture, and stories of the area.

Whether you’re interested in learning about the city’s founding fathers or seeing the grandeur of its post-Industrial Revolution architecture, there’s something for everyone on these informative, educational tours.

With an engaging, and often locally-raised tour guide who shares their passion and knowledge of Portland’s past, visitors will learn about everything from the city’s maritime history to its vibrant food culture.

So put on your walking shoes and get ready to explore the past of this beautiful city!

Walking Tours Portland Maine: History Tours

1. a walk through time tour in portland.

~$50/two ppl

If you’re looking to explore Portland’s history, join this captivating walking tour. You’ll have the opportunity to view many amazing attractions throughout the historic cobblestone streets of Old Port, downtown, and the waterfront area.

Your experienced guide will share intriguing stories of Portland’s rich past. Snacks are provided for all participants and group sizes are capped at 20 people!

Book, or Learn More About A Walk Through Time Here

2. Portland Hidden Histories Walking Tour

~$49/Two ppl

Discover Portland’s unique culture as you explore the city with a local guide. Learn about the tenacious souls who have shaped Portland’s identity through centuries of rebuilding, uncovering stories both inspiring and awe-inspiring.

As you wander down historic avenues, your curiosity for this vibrant destination will be sure to grow! Explore the eons of history in Portland’s historic Old Port and working waterfront on this Hidden Histories Tour!

Feel the palpable presence of Indigenous Wabanaki leaders’ earliest relationships with European colonizers as you are taken through a 1.5-mile route along historic streets like Congress Street, The Old Port, and Commercial Street.

This tour offers an exclusive collection of hidden histories over the course of the 2-hour walking tour that are not offered in other tours. It is sure to be entertaining and informative all at once!

Book, or Learn More About Hidden Histories Tour Here

3. Portland Black History Walking Tour

~$49/two adults

Step back in time and see the journey of the Black Portlanders who strived to move our city, state, and nation toward freedom, democracy, opportunity, and equality.

The success of Maine’s early settlements was propelled by Black labor, expertise and intelligence – all while they continually fought against oppression in order to gain power. Join this guided tour that will walk you through these monumental moments!

Explore the incredible history of Maine and some legendary people of the area with the Portland Black History Tour. With two hours of captivating narration, you will journey 1.5 miles through the Old Port and East End neighborhoods.

You’ll discover stories that are often overlooked in traditional tours- such as those who founded local communities, overturned slavery statewide, drove maritime industries, gained political influence, and fought for equal rights.

Created by uncovering piles of research and historic documents, this tour will open your eyes to a different, and unexpected, history.

Book, or Learn More About Black History Walking Tour Here

4. Portland Women’s History Walking Tour

Portland women have served as driving forces of the city’s culture and national progress toward equality.

Listen to the stories of incredible women, such as the Indigenous Penobscot performer who shifted immigration policy, a Chinese immigrant laundress named American Mother of the Year, a white tavern keeper confronting British Navy ships, and an enslaved Black maid abolishing slavery in her state!

Their indomitable spirit shines through their outstanding accomplishments both within factories and on ballots. Unlock the captivating charm and rich history of a city that was almost lost had it not been for the substantial power of women.

Hear stories told with humor, heart, and abundant enthusiasm by your guide, a Portland native. Explore museums, grand row houses, noble churches, and flawless Federal-style mansions on this two-hour walking tour across 1.3 miles through Portland’s Arts District and West End neighborhood!

Book, or Learn More About Portland Women’s History Walking Tour Here

5. Downtown Portland: Coastal Vibe and Old Mansions

During this self-guided tour, you’ll embark on an enlightening journey as you go back in time to the City Hall, where a rich history awaits.

You’ll be in good hands with your tour guide who will then lead you down Congress Street – Portland’s most celebrated thoroughfare – and introduce you to iconic and historic landmarks such as Monument Square, the Wadsworth-Longfellow House, and the Museum of Art.

Afterward, explore the city’s architectural masterpiece: Victoria Mansion. Boasting an impressive and intricate Italianate design, it is one of the area’s prized attractions. Then, make your way to Old Port, an amazing port district with plenty of historical charm.

Wander through its antique stores, art galleries, and picturesque buildings for hours on end, or enjoy some delicious seafood in any one of its top-rated restaurants! Old Port is one of the best places in Portland to do all those things all within a short distance of each other.

When you return to Congress Street, prepare to be awestruck by the grandeur of the Gothic Cathedral of the Immaculate Conception. You’ll also have an opportunity to climb up the Portland Observatory for unbeatable 360-degree scenic views!

To top it off, the tour will conclude at the Eastern Promenade where spectacular ocean vistas and a myriad of historical monuments await—it’s sure to create lasting memories of your stay in Portland.

Book, or Learn More About Coastal Vibes & Old Mansions Here

Walking Tours Portland Maine: Culinary Tours

✅ Walking Tours: Portland, Maine’s Culinary Scene

If you’re a foodie, then Portland, Maine is the perfect destination for you! With its abundance of delicious eateries and unique culinary experiences, it’s no surprise that many people flock to this city to sample its cuisine-it’s definitely home to the hottest restaurants in the state.

(While Portland restaurants might dominate, there are amazing fine dining spots around the state as well. )

Now, you’ll have the chance to explore the best restaurants in town on foot – with walking tours of Portland Maine’s culinary scene. From enticing seafood restaurants to mouthwatering bakeries, these guided tours offer a tasty exploration of the city’s best eateries.

Learn about the area’s unique food culture as you sample local specialties and get behind-the-scenes looks at some of Portland, Maine’s best restaurants. So grab your appetite and get ready for an unforgettable foodie adventure!

6. Old Port Culinary Walking Tour from Portland

~$140/two ppl

Aspiring epicures can wander through Portland’s picturesque Old Port on their own, but to expose the city’s hidden gems and authentic culinary delights, a Maine foodie tour with a reliable guide is the best bet.

Uncover all that Portland has to offer with this guided foodie tour. You’ll visit up to six eateries and tantalize your taste buds with enough samples for an entire meal! With one exciting tour, you get an unforgettable experience of some of Maine’s finest fare.

With no more than 14 travelers, you’ll get familiar with the local food as your guide regales stories about Portland’s lively culinary scene. Visit five to six eateries along Commercial Street in the heart of Old Port and savor delicious Maine-inspired cuisine!

Book, or Learn More About The Old Port Culinary Walking Tour Here

7. Donut Tasting Walking Tour: Portland’s Old Port

~$45/two ppl

Portland, Maine has made a name for itself as one of the top culinary hotspots nationwide. Okay, so you might not think of donuts when you think culinary tour, but that would be a mistake!

On this tour, you’ll get an awesome opportunity to savor some of the city’s best donuts while also gaining insight into its remarkable history! Your guide will take you to The Holy Donut (famed everywhere!), and you won’t have to wait in line!

You’ll also visit other local favorites that are equally delicious. What an awesome memory–an unforgettable journey through Portland’s delectable doughnut scene!

Book, or Learn More About Donut Tasting Walking Tour Here

✅ Walking Tours: Portland, Maine’s Beer Scene

Portland, Maine is becoming a well-known destination for its craft beer scene. With so many breweries to choose from, it can be hard to know where to start. But now, visitors can explore the city’s best beer offerings on foot!

Guided walking tours of Portland Maine’s beer scene offer a unique opportunity to get in some craft beer tastings while learning about its history. Get an insider look at the area’s breweries as you sip your way through this beautiful city.

So grab a map and get ready for an adventure that takes you to the best beer spots in Portland!

8. Old Port Walk, Talk, and Taste Brewery Tour

~$87/two people

Take a guided, leisurely, walking tour and discover the storied past of Portland’s waterfront.

Explore prohibition-era landmarks as you learn about importing goods to the area while sampling delicious beer from three iconic local breweries: Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company.

Travel in small groups with an experienced local guide on comfortable minibuses (though you are walking for the tour of the breweries) for maximum enjoyment. Snacks and beverages are included throughout your journey, plus convenient pickup services at our centrally located meeting point!

Book, or Learn More About Old Port, Walk, Talk, and Taste Tour Here

Walking Tours Portland Maine: Scavenger Hunts

✅ Walking Tours (sort of): Do a Portland, Maine Scavenger Hunt

Like a self-guided tour but better, because you get to experience the sights and sounds of Portland, Maine like never before – by taking part in a fun-filled scavenger hunt at your own pace! Guided scavenger hunts are a really fun way to explore this charming city.

As you wander through the streets of Portland, you’ll get to experience its vibrant culture while discovering hidden gems tucked away in unlikely places. With exciting tasks to complete and interesting facts about the city to uncover, you’ll have a blast as you make your way through town.

Portland is full of surprises, so take part in this unique activity and explore the city like a local. With the help of your friendly (remote) guide, you’ll get to experience Portland from a new perspective and gain a better understanding of its culture and history.

And with fun tasks to complete along the way, you’re sure to have an adventure you won’t soon forget. So grab your map, pick up a few clues, and get ready for an unforgettable scavenger hunt in Portland, Maine!

9. Portland Scavenger Hunt: The Maine Event

~$12/ two ppl

Are you craving a thrilling outdoor activity in Portland? The Let’s Roam scavenger hunt app has the answer! Whether you’re from here or somewhere else, this is sure to make a fun afternoon of wandering the city.

Get ready for some exploration on foot and discover what Portland has to offer. See if you have what it takes by taking pictures, racing against time limits, and navigating your way through locations like Congress Street and Old Port with The Maine Event Scavenger Hunt!

Book, or Learn More About The Maine Event Scavenger Hunt Here

10. Portland, Maine Madness Scavenger Hunt

~$28/two ppl

Unlike with most scavenger hunts, guests get their own remote host to help and motivate them along the way. These specially crafted adventures blend tour-like elements with creative challenges and detective hunts that the whole family can enjoy.

You’ll uncover off-the-beaten-path gems and creatively interpret clues related to art, history, and culture – all for points! Ready to take your talents global and make a name for yourself? You can compete with teams from all over the world for international fame and glory!

Plus, even if there’s no competition in sight near where you live, it doesn’t mean that fun should be out of reach. You’ll still get a chance to shine by showcasing your favorite hangouts or uncovering unusual oddities along the way.

Book, or Learn More About Maine Madness Here

11. Scavenger Hunt in Portland, Maine by Zombie Scavengers

Are you ready to face the ultimate challenge? Portland is calling and it needs your help! With Zombie Scavengers, you will have the opportunity to explore this city in search of essential items required for surviving a zombie apocalypse.

You’ll earn points each time you find something – but that’s not all: complete some thrilling zombie-themed challenges on the app for extra points! Strategize carefully if you want to amass as many points as possible and avoid becoming a victim of this merciless apocalypse.

Don’t worry; they’ve got your back with their remote host available through chat in case anything goes wrong. So, can YOU survive an epic battle against zombies in Portland?

Book, or Learn More About Zombie Scavengers Here

12. Unique Wacky Walks Scavenger Hunt

~$10/two ppl

Join Wacky Walks on an exciting scavenger hunt around Portland and become the King or Queen of your group as you compete with others. The app-based game will lead you to locate hidden items in the city while also completing fun tasks along the way.

As a reward for finding each item and finishing these missions, points are awarded to players. Gain the highest possible score and be crowned King or Queen of Portland for a day by playing Wacky Walks!

With no time limit, take your time exploring the city as you play. Not to worry if you need assistance – the host will always be on hand through chat support.

Book, or Learn More About Wacky Walks Scavenger Hunt Here

13. Crazy Dash Scavenger Hunt Adventure

Discover Portland like never before with Crazy Dash! The app and the remote host provide a checklist of thrilling tasks to complete and exciting locations to explore. You are free to visit them in any order you choose, earning points along the way for each challenge completed or object found.

Best of all, there is no time limit on this laid-back adventure, so you can take your time exploring the fantastic city that is Portland! In addition, the helpful remote host will be available throughout your game if assistance is ever needed.

Book, or Learn More About Crazy Dash Scavenger Hunt Here

14. Operation City Quest Scavenger Hunt

Ready to discover Portland? Look no further than Operation City Quest! Download the app and complete tasks all around the city for points. Whether you decide to start with an item or challenge is completely up to you!

Track your progress on the leaderboard, and don’t forget about the helpful remote host ready via chat if problems occur during your journey.

Book, or Learn More About Operation City Quest Scavenger Hunt Here

15. 3Quest Challenge Scavenger Hunt

Take a tour of Portland in an entirely unique way, with the 3Quest Challenge! Download the app and explore the city following clues written as riddles. As you complete tasks, collect points to check your ranking on the leaderboard.

Whether competing with friends or colleagues, find out who will be crowned victor at this exciting scavenger hunt! Take on three quests and explore the city of Portland in just two hours! All you need is your wits, and a remote host to assist virtually along the way.

Divide up objects and tasks into 3 different excursions: first quest, second quest, and third quest; finish them one by one to complete the game. Set yourself a time limit if you want more of a challenge!

Book, or Learn More About 3Quest Challenge Scavenger Hunt Here

16. Portland Freedom Trail

$0/Self-guided

Experience Portland, Maine’s history and culture like never before with a self-guided walking tour on the Freedom Trail. This exciting journey takes visitors through some of the city’s most significant locations and attractions, highlighting important stops along the Underground Railroad.

Learn about this powerful movement as you explore churches, schools, homes, and businesses that played a role in helping thousands of enslaved African Americans find freedom. You’ll also gain a better understanding of the city’s past.

Get The Self-Guided Portland Freedom Trail Map Here

Conclusion: Walking Tours in Portland Maine

As you can tell, there are many Portland walking tours for you to choose from–Maine foodie tours, brewery tours, educational tours about the (surprising stories) and people who made Portland what it is today, and some plain old fun tours like the scavenger hunts.

If walking tours of Portland aren’t your thing, maybe a boat tour of Casco Bay, or a bus tour of local breweries is more your style.

No matter what you choose, you’re sure to have a great time sightseeing and learning something new on any of these Portland tours. It’s an amazing city, and experiencing it on foot is really the best way to tour Portland.

If you’re not from the area and want to avoid having to take a car at all, here are some great Portland hotels with free airport shuttles . Several of the hotels are right downtown, too! This means you could spend all your time without the hassle of renting a car.

If you want to venture a little further away, in the winter, why not try some great skiing just a couple of hours away? During the other seasons, Portland is still close enough that you could take a day trip to Acadia National Park !

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Meet the heart and soul behind Wandering Through Maine – a true New Englander at heart, originally from NH, who found their forever home in the beautiful state of Maine. Maine called to them like a lighthouse beacon, and they've embraced it wholeheartedly ever since. This blog isn't just a guide; it's a heartfelt invitation from someone who's walked the trails, sailed the waters, and knows Maine not just as a place on the map, but as a vibrant community and an adventurer's paradise that they call home.