3.6 mi
Meteor Crater
The only U.S. city built entirely inside a meteorite impact crater.
US-25E
Crossroads
Gateway to Cumberland Gap at the Kentucky, Virginia & Tennessee border.
Gateway City
Adventure
Your premier gateway to Cumberland Gap National Historical Park.
Est. 1890
Founded
Founded by English investors, named for Middlesbrough, England.
Today in Middlesboro
Monday, September 28, 2026
Happening Today
Knoxville Symphony Chamber Orchestra Performance
Boots, Buckles & Bling New Year's Eve Travis Wayne & Contraband
Board of Mayor and Alderman
Air Quality
Good
AQI 38 · Safe for outdoor activities
#1 Ranked This Week
Featured Local Business
Nineteen19 Grill & Bar
Food & Dining
Family-owned restaurant and bar serving burgers, sushi, steaks, and a variety of appetizers.
Community Life
Upcoming Events
Agenda Meeting
September 28, 2026
6:00 PM
Cumberland Gap Town Hall
Cumberland Gap National Historical Park Ranger-Led Programs
September 28, 2026
All Day
Cumberland Gap National Historical Park, Middlesboro, KY
Ranger-Led Programs
September 28, 2026
Check Schedule
Cumberland Gap National Historical Park
Gap Cave Tours
September 28, 2026
All Day
Cumberland Gap National Historical Park, Middlesboro, KY
Local Directory
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Find exactly what you're looking for across Middlesboro
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Things To Do in Middlesboro
National parks, crater views, trails, and genuine small-town Kentucky hospitality.
Cumberland Gap
America's first gateway to the West — Pinnacle Overlook, Gap Cave, and 85+ miles of trails in the national park.
Learn more
Fern Lake
Scenic mountain reservoir offering fishing, boating, and stunning views just south of Middlesboro.
Learn moreWilderness Road
Walk in the footsteps of Daniel Boone through the historic Cumberland Gap pass.
Learn more
Downtown & Dining
Historic Cumberland Avenue shopping, local eateries, and community gatherings year-round.
Learn moreLocal Directory
Featured Businesses
Alexander Arthur Museum
A local museum displaying artifacts related to Alexander Arthur, the founder of Middlesboro, located in a historically significant building.
2215 Cumberland Ave, Middlesboro, KY 40965
606-269-1568
Bell County Historical Society and Museum
A local history museum housed in a historic 1912 Carnegie Library building featuring exhibits on regional culture and mining.
207 N 20th St, Middlesboro, KY 40965
606-242-0005
Cumberland Gap National Historical Park Visitor Center
The main hub for the park featuring exhibits, educational films about the area's history, a gift shop, and hiking trail access.
91 Bartlett Park Rd, Middlesboro, KY 40965
606-248-2817
Aspen Dental
A dental office providing preventative, restorative, cosmetic, and emergency dental services with same-day availability.
1238 N 12th St, Middlesboro, KY 40965
606-302-9038
Barton Esthetic and Family Dentistry
A dental practice providing comprehensive care including exams, cosmetic dentistry, and emergency services.
2205 W Cumberland Ave, Middlesboro, KY 40965
606-248-3674
Econo Lodge Middlesboro
A classic motel offering updated, clean rooms, free parking, and a seasonal outdoor pool near local attractions.
1623 Cumberland Avenue, Middlesboro, KY 40965
606-248-5630
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