Middlesboro,
Kentucky
The City Built in a Crater — heritage, nature, community, and small-town charm at the gateway to Cumberland Gap.
66°F
Mainly Clear · Middlesboro, KY
H: 69° · L: 54° · Wind 2 mph
Thursday, November 5, 2026
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
Thursday, November 5, 2026 (ET)
Next Verified Community Events
Bell County Chamber of Commerce Monthly Networking Luncheon
Middlesboro City Council Regular Monthly Session
Veterans Day Program at Cumberland Gap National Historical Park
Live Weather & Air Quality
66°F · Mainly Clear
US AQI 24 (Good) · Updated Nov 5, 2026, 10:22 AM EST
KYTC GoKY Traffic & Conditions
Live US-25E, Cumberland Gap Tunnel, and Bell County highway conditions via Kentucky Transportation Cabinet.
View GoKY MapCity Updates
Local News
#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
Bell County Chamber of Commerce Monthly Networking Luncheon
November 6, 2026
11:30 AM – 1:00 PM
189 N 20th Street, Middlesboro, KY
Middlesboro City Council Regular Monthly Session
November 9, 2026
6:00 PM
Middlesboro City Hall, 221 N 21st Street
Veterans Day Program at Cumberland Gap National Historical Park
November 11, 2026
9:00 AM – 4:00 PM
Cumberland Gap Visitor Center, 100 Pinnacle View Rd
Middlesboro Independent Schools Thanksgiving Break
November 24, 2026
All Day (Nov 24–27)
Middlesboro Independent School District
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 moreFern 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 moreDowntown & Dining
Historic Cumberland Avenue shopping, local eateries, and community gatherings year-round.
Learn moreLocal Directory
Featured Businesses
Pizza Hut
Chain pizzeria serving a variety of pizzas, wings, pasta, and desserts for carryout and delivery.
725 US Hwy 25 E, Middlesboro, KY 40965
(606) 248-7338
Angelo's in the Gap
Italian restaurant in a historic building offering pizzas, calzones, and classic pasta dishes.
527 Colwyn Street, Cumberland Gap, TN 37724
Nineteen19 Grill & Bar
Family-owned restaurant and bar serving burgers, sushi, steaks, and a variety of appetizers.
602 Colwyn Avenue, Cumberland Gap, TN 37724
(423) 259-5019
The Table Coffee House
A cozy cafe offering fresh coffee, lattes, homemade pastries, breakfast, and lunch items.
1100 N 25th St, Middlesboro, KY 40965
(606) 302-5152
Cracker Barrel Old Country Store
Restaurant chain serving Southern-style breakfast, lunch, and dinner in a country-themed setting.
1049 N 12th St, Middlesboro, KY 40965
(606) 248-7011
KFC
Fast-food chain specializing in fried chicken, biscuits, and sides.
1217 East Cumberland Avenue, Middlesboro, KY 40965
(606) 248-3484
This Week in Middlesboro
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