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.