visit middlesboro ky

Home » Travel Guides » United States » Kentucky (KY) » 15 Best Things to Do in Middlesboro (KY)

15 Best Things to Do in Middlesboro (KY)

Nicknamed “Crater City”, Middlesboro has a one-of-a-kind location, in the middle of a meteorite crater three miles in diameter.

On the east side is the Cumberland Gap, a pass in the lower central Applachians and the gateway to the west in 1775 for trailblazer Daniel Boone and the legions of settlers who came after him.

The Cumberland Gap is now part of a massive national park, containing a long stretch of Boone’s Wilderness Trail, the KY-TN-VA Tri-State Point and a whole catalog of memorable sights and experiences.

Middlesboro grew up in the 1880s, and was founded by the Scottish-born Canadian businessman Alexander Alan Arthur, who had ambitious but unrealized plans for a “Magic City”.

The town soon became an industrial center in the Eastern Coalfields, and thought to be the place where pianist Ben Harney invented ragtime in the 1890s.

1. Cumberland Gap National Historical Park

Middlesboro is at the foot of a natural pass in the Appalachian Mountains, at an elevation of 1,631 feet.

Named for Prince William, Duke of Cumberland in 1750, the Cumberland Gap served as a westward passageway for explorers and frontiersmen like Thomas Walker (1715-1794) and Daniel Boone (1734-1820), and then hundreds of thousands of early settlers pouring into Kentucky in their wake.

Later, the pass held real strategic importance in the Civil War, and was the scene of several engagements in 1862 and 1863.

The national park, founded in 1966, covers more than 20,500 acres and offers tons of activities, especially here on the western side.

There are 70 miles of trails here, many imbued with rich historical interest, like the Wilderness Road Trail where you can follow in the footsteps of Daniel Boone on a path trodden by Native Americans since time immemorial.

2. Cumberland Gap National Historical Park Visitor Center

Heading from Middlesboro, the first thing to greet you at Cumberland Gap National Historical Park is the modern Visitor Center, a natural starting point for your adventure.

You can book ranger-led experiences here, like the trip to Gap Cave, and seek out advice on the many self-guided activities on offer in the park.

There are hands-on museum exhibits making clear the huge historical importance of the Cumberland Gap and the Wilderness Trail, in peacetime and war.

Take the time to watch the two HD movies screened at the center: Daniel Boone and the Westward Movement, and The Cumberland Gap, detailing the natural and historical details that you can discover around the national park.

3. Wilderness Road Trail

One of the great experiences in the Cumberland Gap National Historical Park is walking the very path taken by Daniel Boone, many thousands of early settlers and Civil War Soldiers in the 1700s and 1800s, as well as the Native Americans before them.

Leading off from the Thomas Walker Parking Area, the trail will lead you to an historical marker for the Cumberland Gap where the momentous history of the route will become clear.

Along the way are spurs for the KY-TN-VA Tri-State Point, Pinnacle Overlook, Gap Cave, and the remnants of an iron furnace in use for much of the 19th century.

This route eventually connects with the Daniel Boone Trail, rambling eastwards for several more miles and in turn linking with a much larger trail system.

You can stop at the Daniel Boone Visitor Information Center, with exhibits bringing to life the sights and sounds along the Wilderness Road 200+ years ago.

4. Pinnacle Overlook

The parking lot for this exhilarating vantage point in the Cumberland Gap National Historical Park is up the winding Skyland Road, past the trailheads for the Wilderness Road Trail and Tri-State Point Trail.

If you’re feeling energetic you can also pick up the walking trail at the Thomas Walker Parking Area. The path from the upper parking lot leads you across the Kentucky-Virginia State line to a perch where you’ll be confronted by the most iconic vista in the national park.

The Cumberland Gap winds out 900 feet below in all its glory, and as you contemplate this view you can reflect on the pioneers and thousands of early settlers who traveled this pass on their way into Kentucky, as well as the Native Americans who blazed the trail for generations.

Interpretive signs point out some of the landmarks, including the KY-TN-VA Tri-State Point and recall some of the history.

5. KY-TN-VA Tri-State Point

If you’re an active traveler you need to plan a hike to the summit of the 1,990-foot Tri-State Peak, at the tripoint of the states of Kentucky, Tennessee and Virginia.

This mountain forms the “saddle” of the Cumberland Gap and can be reached along the out-and-back Tri-State Peak Trail, which is just over four miles total, with an elevation gain of more than 620 feet.

Beginning in the Thomas Walker Parking Area and departing from the main trail at the Cumberland Gap Marker, the climb is stiff but not onerous, and is clearly marked.

There’s a monument at the top paving the state lines, and you can soak up distant views to go with the satisfaction of being in three states at once.

6. Gap Cave

Among the numerous caves in the national park is Gap Cave, which has more than 18 miles of surveyed tunnels, making it the 4th longest cave system in the country.

The cave was actually on private land until as recently as 1992 when the first commercial tours started. This is a two-hour guided experience in the company of a park ranger.

You’ll start out on the Wilderness Road Trail, before heading up to explore five different levels of the cave, with glimmering stalagmites, flowstone cascades and a surprising amount of wildlife.

Six different bat species have been recorded here, and little brown bats, big brown bats, the northern long-eared bat and the eastern pipistrelle bat are commonly sighted on tours.

7. Abraham Lincoln Library and Museum

Less than ten minutes away in Harrogate, TN is an attraction with one of the largest private Lincoln and Civil War collections in the United States.

The Abraham Lincoln Library and Museum is on the Lincoln Memorial University campus and has recently reopened following a two-year, multimillion-dollar renovation.

The exhibits trace Lincoln’s journey from the frontier to the world stage, investigate some of the political challenges he faced, chart his final days and reflect on his legacy.

Some exciting artifacts include the cane Lincoln carried on the night of his assassination, two life masks, a lock of his hair from his deathbed and a host of other personal items.

The library has an impressive inventory of 30,000+ books, manuscripts, paintings and sculptures, while there’s also an extensive array of Confederate weapons and medical instruments from the field.

8. Pine Mountain State Resort Park

Kentucky’s first state park opened in 1924, a short way north of Middlesboro and just outside Pineville. There are 12 miles of hiking trails at pine mountain, including one to the peak to see the remarkable Chained Rock.

This landmark was created in the 1930s when a 101-foot chain was hoisted between the top of pine mountain and a massive boulder that looms over Pineville.

The story goes that the chain is the only thing preventing the boulder from rolling down the slope and causing a catastrophe. The high elevation at Pine Mountain creates a habitat for passerine bird species normally found much further north, so this is a true birding paradise.

Among the park’s many other features there’s a guest lodge, the Mountain View Restaurant, a number of cabins, an 18-hole golf course and a 9-hole miniature golf course.

9. Downtown Middlesboro

With the rim of the crater visible in all directions, Middlesboro central commercial district has a character of its own.

The district is on the National Register of Historic Places, and among the 60+ contributing buildings are the palatial Old City Hall, the Classical Revival Post Office building (1915), the Carnegie Library (1908) and the curious Coal House (1942), actually built from coal and now home to the Chamber of Commerce.

The linchpin is Fountain Square, named for the fountain on each corner of the intersection of Cumberland Ave and 20th St, and within a few steps are dining spots like the much-loved Shades Café & Steakhouse, as well as options for pizza, Japanese, Chinese, Mexican and classic fast food at Conley’s Drive-In.

A once vacant downtown has become a permanent stage for Middlesboro acclaimed summer concert series, and there’s a bustling indoor farmers’ market, open Fridays.

10. Bell County Historical Society Museum

To get a handle on Middlesboro and Bell County’s past there’s a local history museum in the Middlesboro Downtown Commercial District.

The location is the historic Carnegie Library, opened in 1908. This small but diverting attraction explores the rich cultural heritage of the area, from Daniel Boone to ragtime.

You’ll find out about the experiences of pioneers along the Wilderness Road and Cumberland Gap, and get to know Middlesboro’s origins as a planned community and a center of iron production and coal mining.

All kinds of items, hair curling machines to old pianos, paint a picture of changing lifestyles in Bell County, and there are detailed exhibits about important local figures like actor Lee Majors, who grew up in Middlesboro in the 1940s and 50s.

11. Little Congress Bicycle Museum

A worthwhile detour in Cumberland Gap, TN is an endearing one-room museum founded in 2003 by bicycle collector and Senior Judge at the Kentucky Court of Justice, R.E. McClanahan.

Set next to a charming millrace the Little Congress Bicycle Museum celebrates the vast cultural impact of this enduring mode of transport.

Among the noteworthy picks from a large, rotating collection, there’s a 1950-51 Monark Super Deluxe, a 1969 Lemon Peeler, a 1950 Schwinn Panther D-27 and a 1940 Elgin, sold exclusively by mail order from the Sears catalog.

These bikes are mounted on the walls three-high and accompanied by posters and interpretive materials.

12. Middlesboro Country Club

Welcoming visitors, Middlesboro Country Club is claimed to be the oldest continuously played golf course in the United States.

These nine holes were laid out in the 1880s as part of Alexander Arthur’s original plan for his “Magic City”. The course is believed to be at the very center of impact for the giant crater that holds the town.

For decades, this was home to one of the few par 6 (660 yards) holes in the country (7th hole), and even though this hole has been shortened it’s notoriously difficult to reach the green in fewer than three shots.

13. Cannon Creek Lake

North of Middlesboro on U.S. 25e there’s a 250-acre reservoir constructed in the early 1970s. Apart from a boat ramp, Cannon Creek Lake hasn’t been developed much for recreation, which is part of its charm.

There is much on the shore apart from an unpaved and unmarked trail through the woods. You can boat, fish or paddle here in perfect seclusion, with no signs of civilization on the steep, wooded shores.

If you’re here for fishing you can expect to catch largemouth bass, smallmouth bass, bluegill, channel catfish and rainbow trout.

14. Middlesboro Mall

Along 12th St (U.S. 25e) there’s a commercial corridor in Middlesboro, home to a succession of supermarkets, department stores and chain restaurants.

In this remote corner of southeastern Kentucky, you’ll be many miles from the next nearest location for most of these brands.

The main enclosed shopping center is the Middlesboro Mall and has branches of Belk, rue21 and Factory Connection, among a slew of local shops and services.

Close by there’s a Kroger, Walmart Supercenter and chain restaurants for the likes of Arby’s, Papa Johns, Rally’s, Wendy’s and Taco Bell.

15. Golden Ticket Cinemas Middlesboro 4

At the north end of Middlesboro Mall is a compact, four-plex movie theater that has changed hands a few times in the last decade.

The cinema was opened by Carmike, which was taken over by AMC in 2016. This AMC location closed down for good during Covid, but was soon acquired by the Golden Ticket Cinemas chain.

It remains a cozy place to watch first-run releases with ample, comfortable seating and a reasonable price point considering the modern amenities. At the time of writing this article, matinees were just $6.50, and Super Tuesdays were $5.50 for all shows, all day.

15 Best Things to Do in Middlesboro (KY):

• Cumberland Gap National Historical Park
• Cumberland Gap National Historical Park Visitor Center
• Wilderness Road Trail
• Pinnacle Overlook
• KY-TN-VA Tri-State Point
• Abraham Lincoln Library and Museum
• Pine Mountain State Resort Park
• Downtown Middlesboro
• Bell County Historical Society Museum
• Little Congress Bicycle Museum
• Middlesboro Country Club
• Cannon Creek Lake
• Middlesboro Mall
• Golden Ticket Cinemas Middlesboro 4

Boone's Ridge - Coming 2024 Click Picture Below For Website

Attractions

Cumberland Gap National Historical Park

Location: 91 Bartlett Park Rd / Middlesboro, KY 40965

Phone: 606-248-2817

Website: https://www.nps.gov/cuga/index.htm

Come visit one of the premier national parks in the entire country in Cumberland Gap National Historical Park. You can walk in the footsteps of Daniel Boone and America’s first pioneers who discovered the first gateway to the west. The park offers over 85 miles of hiking trails, horseback riding opportunities, as well as back-country camping. Make sure to check out the Visitors Center just outside of Middlesboro, KY on Highway 25E. Also, the park has some fantastic points of interest, including the Pinnacle Overlook, the Tri-State marker, Gap Cave (tour information on park website), and Hensley Settlement (tour information on park website).

Photo by Harold Jarrell

Hensley Settlement 

Ever want to take a step back in time and see what life was like in the early pioneer days in Appalachia? A trip to historic Hensley Settlement allows you to do just that. This old mountain settlement sits atop Brush Mountain at an elevation of 3,000+ feet. It once housed multiple families and over 200 residents. Cabins, barns, and even a school house are still located on the settlement and the Cumberland Gap National Park has schedule tours for your convenience. The 2016 tour schedule is as follows:

Prices Adults- $10.00 Visitors with Golden Age, Interagency Senior Pass or Access Pass - $5.00 Children under the age of 12 - $5.00

May 15 - October 31 (No shuttle offered August 13- 14) Sunday, Tuesday and Thursday Depart 12:30 pm; return 4:30 pm

Monday, Wednesday, Friday, and Saturday Depart 9:00 am; return 1:00 pm

Pinnacle Overlook 

Click here for location 

Website : https://www.nps.gov/cuga/index.htm

Description : The Pinnacle Overlook boasts one of the most breath-taking, spectacular views in all of Appalachia. Located just a few miles from the visitor center, you can follow the signs up a windy black top road to the top of the Cumberland Mountain. At the top you will reach a parking lot, and just a few steps away from the parking area you follow a short path to the overlook pavilion, where can stare in amazement at the very best scenery that Appalachia has to offer. Views into all three states (KY, TN, and VA) can be seen from this overlook. Not far from the overlook is the Three-State marker, where you can stand in all three states at one time.

After years of being closed to the public, the National Park has began to give guided tours of the famous Gap Cave (also known in the past as Cujo’s Cave). This is one of the most unique attractions in the entire area, and it’s a great activity to check out in the summertime since the cave stays nice and cool.

Join park rangers on an exciting two-hour adventure exploring this  majestic underground cathedral!  Discover glistening stalagmites and flowstone cascades. You might even catch a glimpse of a bat or salamander.

September 1 - September 30: Wednesdays, Thursdays, Fridays, and Saturdays at 10 a.m.

How to participate in a Gap Cave Tour:

REQUIRED! Make a reservation, by noon the day before desired tour date

Come to visitor center and pay for your tour at least 30 minutes before your tour starts

Meet at Daniel Boone Parking and Exhibit Area at least 15 minutes before your tour starts

Pine Mountain State Park Lodge

Location: 1050 State Park Rd / Pineville, KY 40977

Phone:  (606) 337-3066

Website:   http://parks.ky.gov/parks/resortparks/pine-mountain/

Kentucky’s first state park is a hidden gem in the Commonwealth. Located just south of Pineville, KY, the park has over 15 miles of some of the finest hiking trails in all of Appalachia including favorites like Hemlock Garden Trail, Honeymoon Falls Trail, Chain Rock Trail, and much more. The park has an adjacent 18-hole golf course in Wasioto Winds, a lodge with both rooms and cabins for rent, and a brand new zip line and canopy tour (see below). Visitors can also enjoy many fantastic overlooks, including the famed Chain Rock Overlook that overlooks Pineville.

Click here for Location

Chain Rock is a unique point of interest that sits within Pine Mountain State Resort Park. From the parking lot at the top of Pine Mountain, it is a short hike to the Chain Rock overlook. There, legend has it, the chain was put between two large boulders to keep them from falling onto the town of Pineville. 

Honeymoon Falls

Click Here For Location

Honeymoon Falls is one of the most serene places in all of Appalachia. It consists of two twin waterfalls on either side of the Honeymoon Trail. There is a new staircase that leads up the trail. It is one of the must-see sights within Pine Mountain State Resort Park.   

Wasioto Winds Golf Course (18 Hole)

Click here for location, phone: 1-800-814-8002, website: http://parks.ky.gov/golf/18_hole/pine-mountain/.

Description:  This 18-hole golf course is nestled in shadows of Pine Mountain and offers one of the most spectacular back drops for a game of golf that you can find anywhere in the nation. This eighteen-hole course includes five par 3 holes and five par 5s. True to its links nature, the course is relatively flat, with water coming into play from three lakes, a creek and several wetlands areas. Six arching bridges span the water throughout the course. Other course features include wide car paths, a practice range, and two practice putting greens.

Middlesboro Country Club (9 Hole)

Location:   155 country club ln / middlesboro, ky 40965, phone: (606) 248-7435, website: www.middlesborocountryclub.com.

Middlesboro is home to the oldest continually played golf course in America. It was founded in 1889, the same year as the town, as a way for the English investors and businessmen who were settling in the area to have some recreation. Nestled inside a beautiful circular valley, the golf course was proven to be the center of impact for the meteor that created the unique valley that the city of Middlesboro sits in. The golf course hosts several golf scrambles and events throughout the year, make sure to check out their website for details.

Cannon Creek Lake

Click here for access location map, phone: (606) 248-2482, website: www.bellcountytourism.com.

Description:  This 250-acre impoundment in central Bell County is a phenomenal fishery for largemouth, smallmouth, and Kentucky bass as well as trout, bluegill, crappie and catfish. There are no gas-powered motors allowed on the lake, making it ideal for kayakers. There is access to a boat ramp on Cannon Creek Rd which is located in the Meldrum Community, with access from Old Pineville Pike.

Cumberland River

Click here for hwy 119/hwy 987 take out, click here for hwy 2014 take out .

Description:  The Cumberland River offers opportunities for both kayakers and canoers as well as anglers. Healthy populations of quality smallmouth bass exist, as well as largemouth and Kentucky bass, bluegill, walleye, and catfish. There are currently two-take outs (one under the Wilderness Trail-Off Road Park entrance bridge) which can be accessed at the Hwy 119/Hwy 987 intersection, and another near the Bell County Fairgrounds on Hwy 2014. We are currently working on finding new access points and potential take outs, so stay tuned!

Bell County Historical Society

Click here for location map, phone: (606) 242-0005, website: www.bellcountyhistorical.com.

Description:  The Bell County Historical Society is located right beside the Middlesboro Post Office on 20th St. It houses many artifacts and exhibits pertaining to the county’s history including the Middlesboro meteor crash, coal mining, Indian artifacts, and much more! Hours and info are on website.

SkateWorld 

Phone: (606) 248-0219, website: http://skateworldky.com/.

Description: Skateworld is located on Cumberland Avenue in Middlesboro, KY. This iconic Middlesboro establishment has been around for decades. Skateworld accommodates parties and church groups as well as individual skaters as well. There is also a pro shop within the facility as well. Check the website for prices, hours, and more info! 

Hillcrest Lanes Bowling And More (Harrogate, TN)

Phone: (423) 869-4120, website:  https://www.facebook.com/hillcrestlanesbowlingcenter/.

Description: We have 20 Lanes of Bowling, League Bowling, Pool Tables & Arcade Game Room. We have discounted information for Birthday Parties & Church Groups. Also, if interested in joining and/or being part of a bowling league team, call or come by and see Sherry, James, Joe or Tommy. 

1620 Dorchester Ave / Middlesboro, KY 40965

Phone:(606) 269-4557, website: r c arena | middlesboro ky | facebook.

Description: Just opened in 2022, this amazing indoor RC car dirt track features competitive races all year long! Check out the Facebook page linked above for their schedule. For more info, email them at  [email protected]

Golden Ticket Cinema Movie Theater

Phone: (606) 248-0426, website:   middlesboro 4 - golden ticket cinemas - ticketing, concessions, gift cards, rewards (gtcinemas.com).

Description: Golden Ticket visitors a four cinema theater in the Middlesboro Mall. Located just beside HeHuDarz. Visit website for movies currently playing, showtimes, etc. 

Bell Theater 

Phone: 606-499-0660 or 606-337-2958, website:  https://www.facebook.com/bell-theater-125134245078/.

Description: The newly renovated Bell Theater in Pineville features events of all kinds, from movies to plays to concerts. For upcoming events, please check their Facebook page linked above. 

Wildlife Management Areas

Check out the interactive map of  the wildlife management areas below., click link for more map info:  https://app.fw.ky.gov/public_lands_search/.

Corrigan Wildlife Management Area

Phone: (606) 269-8164, website: http://fw.ky.gov/more/documents/corriganwma_all.pdf.

Description:  With over 54,000 acres (the largest parcel of which being a 34,000-acre tract adjacent to Middlesboro), Corrigan Wildlife Management Area offers hunters and anglers the opportunity to enjoy one of the most beautiful pieces of land in Appalachia. On Corrigan WMA, you can enjoy both the remoteness of a vast tract of quintessential Appalachian wilderness while being right beside the city of Middlesboro where you can access lodging, restaurants, shopping, and much more. With hundreds of miles of trails that contain countless breath-taking views of Middlesboro and the Cumberland Gap, as well as hunting opportunities for elk (special restrictions apply, see KDFW website), deer, turkey, grouse, quail, black bear (special restrictions apply, see KDFW website) and much more as well as fishing opportunities in ponds throughout the property as well as nearby Cannon Creek Lake, Corrigan WMA offers outdoor lovers a vast paradise of recreation and solitude while being right beside the city of Middlesboro.   

Shillalah Creek Wildlife Management Area

Click here for fishing access location map , click here for wma access location map, phone: (606) 337-9317, website: http://fw.ky.gov/more/documents/shilalahcreekwma_all.pdf.

Description:  This 2,500-acre wildlife management area not only has great hunting opportunities for white-tail deer, turkey, grouse, black bear (special restrictions apply – see KDFW website for details), and much more. However, the most notable aspect of Shillalah Creek WMA is that it hosts one of only two streams in Kentucky where one can fish for native brook trout. It is also home to great hiking trails, as well as the beautiful Shillalah Falls.

Kentucky Ridge State Forest / Wildlife Management Area

Click here for access location map , phone: (502)-564-4496, website: http://forestry.ky.gov/kentuckysstateforests/pages/kentuckyridgestateforest.aspx.

Description:  This 15,000-acre jewel is located in central Bell County between the cities of Pineville and Middlesboro. It is bordered by Corrigan Wildlife Management area on its southern border. It is dually managed by the Kentucky Division of Forestry and the Kentucky Department of Fish and Wildlife. It is open to not only hunting and fishing, but also horseback riding and primitive camping.

Boone Forestlands Wildlife Management Area

Website: http://fw.ky.gov/more/documents/booneforestlandswma_all.pdf.

Description:  This 30,000 plus acre tract of public hunting land is one of the most likely areas in the entire state to see an elk herd, and some Boone & Crockett elk have been taken from this particular tract. The area consists mainly of reclaimed strip land. The tops are largely open, with vast fields that resemble someplace in Montana rather than Kentucky, and rugged, steep timbered land comprising the mountain slopes. Other wildlife such as black bear, turkey, white tail deer, quail, and grouse can be found on the property.

Fortner Davis Wildlife Management Area

Website:  http://fw.ky.gov/more/documents/fortner-daviswma_all.pdf.

Description:  This tract of land is approximately 1,500 acres that rests on the northern edge of Cannon Creek Lake. It adjoins the Corrigan Wildlife Management Area. There is a gravel road that runs through the center of it, however the gate for access is locked most of the time, so access is by foot only.

Asher Hunter Access Area

Website:  http://fw.ky.gov/more/documents/asherhuntingacccessarea_all.pdf.

Description:  This 8,000 acre plus parcel of land lies in northern Bell County and is bordered by the Boone Forestlands WMA. Wildlife is abundant throughout the property, with elk being regularly seen. This piece of land is one of the most likely places in Bell County to witness an elk herd. Great hunting for whitetail deer, turkey, black bear (special regulations apply), grouse, quail, rabbit, and much more exist. Unlike other Wildlife Management Area, Asher Hunter Access Area allows for more reasonable access possibilities. ATV and horseback riding is allowed for hunting access here.

Elk Forest Wildlife Management Area

Website:  http://fw.ky.gov/more/documents/elkforestwma_all.pdf.

Description:  This WMA lies in Bell, Harlan, Leslie, and Clay counties and is over 16,000 acres of great public hunting. As the name suggests, this WMA is known to have large populations of elk within its boundaries. It is located in a remote section of northern Bell County before crossing into neihboring counties. 

Top Things to Do in Middlesboro, KY

Places to visit in middlesboro, tours near middlesboro.

Downtown Knoxville Hidden Tour w/ Ice Cream, Coffee & Tennessee River Gems

Knoxville Scavenger Hunt: Knoxville's Perfect Blend

Fun City Scavenger Hunt in Knoxville by Crazy Dash

Knoxville’s Country Music Heritage: A Self-Guided Audio Tour

Knoxville Scavenger Hunt Walking Tour and Game

Knoxville Bar Hunt: Swell Times in Scruffy City

Knoxville Scavenger Hunt by Zombie Scavengers

Knoxville City Scavenger Hunt Excursion by Wacky Walks

Participate in a Fun Scavenger Hunt in Knoxville by Operation City Quest

Top attractions in middlesboro.

Other Top Attractions around Middlesboro

What travellers are saying

• Cumberland Gap National Historical Park
• Bell County Historical Society
• Alexander Arthur Museum
• Middlesboro Mall
• Shillalah Creek Wildlife Management Area
• Pinnacle Overlook
• Tri-state Point
• Fords Woods Park

Top Things to Do in Middlesboro, KY

Things to do in middlesboro, tours near middlesboro.

Downtown Knoxville Hidden Tour w/ Ice Cream, Coffee & Tennessee River Gems

Knoxville Scavenger Hunt: Knoxville's Perfect Blend

Fun City Scavenger Hunt in Knoxville by Crazy Dash

Knoxville’s Country Music Heritage: A Self-Guided Audio Tour

Knoxville Scavenger Hunt Walking Tour and Game

Knoxville Bar Hunt: Swell Times in Scruffy City

Knoxville Scavenger Hunt by Zombie Scavengers

Knoxville City Scavenger Hunt Excursion by Wacky Walks

Participate in a Fun Scavenger Hunt in Knoxville by Operation City Quest

Top attractions in middlesboro.

Other Top Attractions around Middlesboro

What travellers are saying

• Cumberland Gap National Historical Park
• Bell County Historical Society
• Alexander Arthur Museum
• Middlesboro Mall
• Shillalah Creek Wildlife Management Area
• Pinnacle Overlook
• Tri-state Point
• Fords Woods Park

Welcome to Middlesboro, Kentucky

We are so excited you're here!

Our mission is to bring life to our historic downtown by developing better opportunities to live, work, sleep, shop and play. our vision is to be the premier destination of southeastern kentucky by preserving our past, bringing together our present community, enriching our future, and providing a space for all to enjoy., featured main street businesses.

The Emporium at 2120

First State Bank of the Southeast

Crater City Coffee Company

Middlesboro Independent School District

Patsy Sullivan

Tim Short Auto

Edward Jones

Green Construction

Commercial   Bank

Community Trust Bank

Learn about all that's happening around Middlesboro (and hear some awesome tunes) on our Downtown radio station.

Your browser is not supported for this experience. We recommend using Chrome, Firefox, Edge, or Safari.

Travel Guide Request

Sign Up Today!

Middlesboro Kentucky

Built entirely within the impact crater of a meteorite, the Kentucky Trail Town of Middlesboro captures the distinct flavors of The Kentucky Wildlands with such attractions as Cumberland Gap National Historic Park, The Coal House (a home built only with bituminous coal) and the 1890 grand Victorian Cumberland Manor Bed & Breakfast. Annual events, such as the Wing Fling Hot Wing Festival and the summertime Levitt Amp Middlesboro Music Series (featuring weekly crater-filling concert performances), add to its charm, along with local favorites like Shades Café & Steakhouse and the A.D. Campbell Co. women’s clothing boutique, one of Middleboro’s oldest and trendiest downtown businesses.

Complete your adventure with a short drive to the Cumberland Gap National Historic Park and enjoy more than 85 miles of hiking trails, including the breathtaking views of the 1,800-foot Pinnacle Overlook (accessible by foot and bike). Visit the nearby Corrigan Wildlife Management Area with more than 54,000 acres of fishing, hiking, hunting, and camping, and the Shillalah Creek Wildlife Management Area, which has its own ample hunting, hiking, camping, and fishing and is home to one of only two Kentucky streams for native brook trout fishing.

Up the road lies Pineville with its historic Main Street, artisan shops and art deco Bell Theater and Playhouse. Nearby Pine Mountain State Resort Park, Kentucky’s historical first state park, features the Chained Rock Trail, waterfalls, Laurel Cove Amphitheater, golfing, charming stone and wood lodge, restaurant, and cottage rentals. 

Bell County Tourism

Hidden Gems in the Kentucky Wildlands

Liberty park veteran's wall.

The Veteran’s Wall is a memorial dedicated to all U.S. Service Members from Liberty...

Asher Hunting Access Area

This area is open to hunting for statewide regulations and rules and regulations in...

Zilpo Road National Forest Scenic Byway

The Zilpo Scenic Byway is a gently curving eleven mile road with a travel time of...

Worth Adding to Your Kentucky Bucket List

Paintsville, art galleries.

The Kentucky Wildlands

2292 South Highway 27, Somerset, KY 42501

P: (606) 677-6150

[email protected]

Social Media

• Privacy Policy

© 2024 All Rights Reserved.

Straddling The Kentucky-Tennessee Border, The Town Of Middlesboro Is One Of The Most Unique Places You'll Ever Visit

Sarah McCosham

I write like it's my job - because it is! I have a Master's in English and love words: crossword puzzles, Scrabble games, Wordle, and, of course, good, old-fashioned books. I'm a writer and editor at OnlyInYourState, and a contributing writer at Cincinnati Magazine. I love the Great Outdoors and am endlessly awestruck by this beautiful country of ours. Coffee keeps me going, yoga keeps me sane, my kids keep me grounded, and my writing keeps me inspired.

More by this Author

From the canyons of Red River Gorge to the shores of Land Between the Lakes, the mountains of Appalachia to small towns and big cities of the Bluegrass, there’s no state more wholly, wonderfully unique than Kentucky. Straddling the Kentucky-Tennessee border, the town of Middlesboro is quite literally an outlier; it’s betwixt and between two Southern states with a unique identity and culture all its own.

Related Stories

You Can Explore Kentucky's Caves By Boat On This Bucket-List Worthy Adventure

Rent Your Own Three-Story Party Boat In Kentucky For An Amazing Time On The Water

See The Bluegrass State's Beauty On The 5 Best Train Rides In Kentucky

Have you visited this unique Kentucky town before? There really is no place like Middlesboro, Kentucky! But then again, there’s no place like home in Kentucky .

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

Want more Kentucky in your inbox?

Get the latest on things to see, do, and eat around Kentucky!

An error occured.

Related Articles

• This 3-Hour Train Ride Is The Most Relaxing Way To Enjoy Kentucky Scenery
• Enjoy The Simple Life When You Visit This Tiny Rural Community In Kentucky
• This Friendly Town In Kentucky Is The Perfect Day Trip Destination
• George Clooney Once Called This Small Town In Kentucky Home And You'll Want To Explore It Yourself
• Few People Realize How Much Mining History Is Preserved In The Small Town Of Blue Heron, Kentucky
• This Summer, Take On A Bourbon Boat Tour For The Ultimate Kentucky Day Trip
• One Of The World's Largest Clocks Is Visible From Downtown Louisville, Kentucky
• Spend A Spring Day Admiring Art And Nature At This Lovely, Little-Known Park In Kentucky

Explore Kentucky

• Arts & Entertainment
• Farms & Wildlife
• Fun Adventures
• Shops & Boutiques
• Sights & Landmarks

Featured Addresses

• Skip to global NPS navigation
• Skip to this park navigation
• Skip to the main content
• Skip to this park information section
• Skip to the footer section

Exiting nps.gov

Alerts in effect, mountain gateway.

Cumberland Gap was the first great gateway to the west. Come follow the path of bison, Native Americans, longhunters, and pioneers. Walk where 300,000 people crossed the Appalachians to settle America. Explore 85 miles of trails and 14,000 acres of wilderness. Stand in 3 states at once. Explore a cave, see Hensley Settlement, or camp under the stars. Come find your connection to Cumberland Gap.

Follow the footsteps of bison, Native Americans, Daniel Boone, and others across the Gap.

Journey with a guide and explore Gap Cave.

Excite the senses and experience central Appalachia through scenic vistas, cascading waterfalls, lush forests, and remote wilderness.

Stroll among the pastoral landscapes and hand-hewn cabins of the historic Hensley Settlement, located high atop Brush Mountain.

Camp at Wilderness Road Campground, which has both electric and non-electric sites, or in the backcountry.

Join a variety of Ranger-led programs about the history and natural beauty of Cumberland Gap.

Explore nearly 85 miles of hiking trails.

Last updated: February 26, 2024

Park footer

Contact info, mailing address:.

91 Bartlett Park Road Middlesboro, KY 40965

606 248-2817

Stay Connected

Explore subjects and stories related to this park.

CITY OF 

MIDDLESBORO

WELCOME TO MIDDLESBORO

Thank you for visiting our website, we hope you find it informative and easy to navigate to have questions answered about Middlesboro and our services. 

Mayor Boone Bowling

UPCOMING EVENTS

City Council Work Session

Held in Council Chambers.

Regularly scheduled council meeting

6:00pm - this will be held at City Hall in Council Chambers.

221 N. 21st Street Middlesboro, Kentucky 40965

​Tel:  606-248-5670

​Fax: 6 06-248-1202

Hours are 8 a.m. until 4 p.m. and we are open through lunch.​​

MIDDLESBORO  APPLICATION FOR EMPLOYMENT

CITY SOCIAL MEDIA

Expedia Rewards is now One Key™

Middlesboro, ky.

Visit Middlesboro

• Middlesboro Hotel Deals
• Vacation Rentals in Middlesboro

Reviewed on Apr 22, 2024

Reviewed on Apr 18, 2024

Reviewed on Jul 31, 2023

Reviewed on Apr 4, 2024

Reviewed on Sep 28, 2023

Check Middlesboro hotel availability

Popular places to visit.

• Middlesboro Mall

You can search for that perfect souvenir at Middlesboro Mall during your visit to Middlesboro. Discover the mountain views while you're in the area.

Middlesboro ARH Hospital

Though Middlesboro ARH Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Middlesboro while you are here.

• Middlesboro Country Club

Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.

Reviews of Middlesboro

5/5 - excellent.

BEAUTIFUL TOWN WITH NICE PEOPLE

Beautiful city and friendly people.

Leaf color great

My stay in the hotel was excellent and I would recommend it everyone

Middlesboro has lots of shopping and is a big town in an area mostly full of smaller towns with fewer shopping and provisioning choices. We enjoyed our stay there.

Quiet area with beautiful mountain views

• Cities near Middlesboro

Cumberland Gap

• Places of interest
• Bell County Historical Society Museum
• Norris Lake
• Daniel Boone National Forest
• University of the Cumberlands
• Cumberland Gap National Historical Park
• Cumberland River
• Pine Mountain State Resort Park
• The Harlan Center
• C.W. Gose Municipal Park
• Indian Mountain State Park
• Straight Creek Boat Dock
• Martins Fork Lake - Smith Recreation Area
• Lone Mountain Boat Dock
• Smith Recreation Area Beach
• Barbourville Water Park
• The Pinnacle
• Wasioto Winds Golf Course
• Dr Thomas Walker State Park
• Boone's Ridge Wildlife Park
• Memorial Park