Things to Do Today in Middlesboro

Find events and activities happening today in Middlesboro. Updated daily with the latest local happenings.

50 results found · Updated 2026-04-07

Things to Do This Weekend Kid-Friendly Free Events Date Night Outdoors Concerts & Live Music Food & Dining Fitness & Sports Arts & Culture

Photo by Perry Merrity II on Unsplash — representative image for Long John Silver's

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Long John Silver's

Middlesboro, KY

Seafood Restaurant in Middlesboro, KY

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Photo by Emily Wassmansdorf on Unsplash — representative image for Civic Center Park

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Civic Center Park

Middlesboro, KY

Park in Middlesboro, KY

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Photo by Eliézer Fernandes on Unsplash — representative image for Bradner Stadium

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Bradner Stadium

Middlesboro, KY

Stadium in Middlesboro, KY

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Photo by Jamie Wheeler on Unsplash — representative image for Shades of Brown

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Shades of Brown

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Karl Callwood on Unsplash — representative image for GOLDEN TICKET CINEMAS MIDDLEBORO 4

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GOLDEN TICKET CINEMAS MIDDLEBORO 4

Middlesboro, KY

General in Middlesboro, KY

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Photo by MChe Lee on Unsplash — representative image for Middlesboro Farmer's Market inside Crater City

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Middlesboro Farmer's Market inside Crater City

Middlesboro, KY

Farmers Market in Middlesboro, KY

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Photo by Barbara Burgess on Unsplash — representative image for Middlesboro Community Center

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Middlesboro Community Center

Middlesboro, KY

Community Meetup in Middlesboro, KY

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Photo by Wes Hicks on Unsplash — representative image for Daniel Boone's Trail

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Daniel Boone's Trail

Middlesboro, KY

Outdoor Space in Middlesboro, KY

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Photo by Yeh Xintong on Unsplash — representative image for Cumberland Gap Mountain Spring Water

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Cumberland Gap Mountain Spring Water

Middlesboro, KY

Bakery in Middlesboro, KY

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Photo by Fabian Blaha on Unsplash — representative image for Rally's

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Rally's

Middlesboro, KY

Fast Food in Middlesboro, KY

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Photo by Vidar Nordli-Mathisen on Unsplash — representative image for DQ Grill & Chill

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DQ Grill & Chill

Middlesboro, KY

Restaurant in Middlesboro, KY

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Photo by Eduardo Soares on Unsplash — representative image for Save A Lot

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Save A Lot

Middlesboro, KY

Grocery in Middlesboro, KY

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Photo by Nathan Dumlao on Unsplash — representative image for The Table Coffee House

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The Table Coffee House

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Sandra Seitamaa on Unsplash — representative image for Food City

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Food City

Middlesboro, KY

Food Drink in Middlesboro, KY

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Photo by Tseinn Wong on Unsplash — representative image for The Pinnacle-Cumberland Gap Tn

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The Pinnacle-Cumberland Gap Tn

Middlesboro, KY

Park in Middlesboro, KY

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Photo by Nathan Dumlao on Unsplash — representative image for Crater City Coffee Company

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Crater City Coffee Company

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Barbara Burgess on Unsplash — representative image for Fellowship Center

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Fellowship Center

Wallins Creek, KY

Community Meetup in Wallins Creek, KY

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Photo by Syed F Hashemi on Unsplash — representative image for KFC

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KFC

Middlesboro, KY

Fried Chicken in Middlesboro, KY

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Photo by Zoshua Colah on Unsplash — representative image for Pine Mountain State Resort Park

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Pine Mountain State Resort Park

Pineville, KY

Hotel in Pineville, KY

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Photo by David Trinks on Unsplash — representative image for He Hu Darz

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He Hu Darz

Middlesboro, KY

General in Middlesboro, KY

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Photo by Gabriele Romano on Unsplash — representative image for Cumberland Gap National Historical Park

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Cumberland Gap National Historical Park

Middlesboro, KY

Park in Middlesboro, KY

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Photo by Caro Schuermans on Unsplash — representative image for Conley's Drive In Restaurant

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Outdoor

Conley's Drive In Restaurant

Middlesboro, KY

Restaurant in Middlesboro, KY

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Photo by mohamed hassouna on Unsplash — representative image for Gem City Cakes

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Outdoor

Gem City Cakes

Pineville, KY

Bakery in Pineville, KY

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Photo by Croissant on Unsplash — representative image for Beans Fork

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Beans Fork

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Xavier Wolf on Unsplash — representative image for Yamato Steakhouse

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Yamato Steakhouse

Middlesboro, KY

Steakhouse in Middlesboro, KY

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Photo by Dimitar Krastev on Unsplash — representative image for Dairy Queen

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Dairy Queen

Middlesboro, KY

Ice Cream in Middlesboro, KY

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Photo by Leonardo Iribe on Unsplash — representative image for Burger King

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Burger King

Middlesboro, KY

Burger Restaurant in Middlesboro, KY

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Photo by Leticia Golubov on Unsplash — representative image for Fords Woods Park

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Fords Woods Park

Middlesboro, KY

Park in Middlesboro, KY

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Photo by David Trinks on Unsplash — representative image for Belk

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Belk

Middlesboro, KY

General in Middlesboro, KY

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Photo by Anna Keibalo on Unsplash — representative image for Sonic Drive In (Sonic Drive-In)

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Outdoor

Sonic Drive In (Sonic Drive-In)

Middlesboro, KY

Fast Food in Middlesboro, KY

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Photo by David Trinks on Unsplash — representative image for Middlesboro Mall

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Middlesboro Mall

Middlesboro, KY

General in Middlesboro, KY

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Photo by Getty Images on Unsplash — representative image for Stinking Creek Knox County

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Stinking Creek Knox County

Flat Lick, KY

Park in Flat Lick, KY

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Photo by Erik Mclean on Unsplash — representative image for Arby's

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Arby's

Middlesboro, KY

Fast Food in Middlesboro, KY

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Photo by Nathan Dumlao on Unsplash — representative image for Mountain Mugs Craft and Coffee

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Mountain Mugs Craft and Coffee

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Дегтярев Николаевич on Unsplash — representative image for Pinnacle Overlook Cumberland Gap National Historical Park

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Pinnacle Overlook Cumberland Gap National Historical Park

Middlesboro, KY

Outdoor Space in Middlesboro, KY

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Photo by Crunch on Unsplash — representative image for Subway

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Subway

Middlesboro, KY

Sandwich Shop in Middlesboro, KY

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Photo by Gabriele Romano on Unsplash — representative image for Shillalah Creek Wildlife Management Area

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Shillalah Creek Wildlife Management Area

Miracle, KY

Park in Miracle, KY

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Photo by Edwin Petrus on Unsplash — representative image for Sagebrush Steakhouse

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Sagebrush Steakhouse

Middlesboro, KY

Restaurant in Middlesboro, KY

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Photo by Do Nhu on Unsplash — representative image for City Sippers

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City Sippers

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Tseinn Wong on Unsplash — representative image for Kay Jay Recreation Park

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Kay Jay Recreation Park

Trosper, KY

Park in Trosper, KY

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Photo by Caro Schuermans on Unsplash — representative image for Middlesboro (Cracker Barrel)

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Middlesboro (Cracker Barrel)

Middlesboro, KY

Restaurant in Middlesboro, KY

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Photo by Emily Wassmansdorf on Unsplash — representative image for Saylor Park L Rev

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Saylor Park L Rev

Pathfork, KY

Park in Pathfork, KY

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Photo by Konstantin Volke on Unsplash — representative image for Kroger

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Kroger

Middlesboro, KY

Grocery in Middlesboro, KY

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Photo by Croissant on Unsplash — representative image for Food City Starbucks - Middlesboro, KY

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Food City Starbucks - Middlesboro, KY

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Mohsen Tebi on Unsplash — representative image for Barbourville City Park

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Barbourville City Park

Barbourville, KY

Park in Barbourville, KY

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Photo by Ana Beatriz Santos on Unsplash — representative image for Goody's

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Goody's

Middlesboro, KY

General in Middlesboro, KY

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Photo by fr0ggy5 on Unsplash — representative image for Ford's Wood Park

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Ford's Wood Park

Middlesboro, KY

Park in Middlesboro, KY

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Photo by Rohani Budi Prihatin on Unsplash — representative image for McDonald's

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McDonald's

Middlesboro, KY

Fast Food in Middlesboro, KY

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Photo by Nathan Dumlao on Unsplash — representative image for Starbucks

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Starbucks

Middlesboro, KY

Coffee Cafe in Middlesboro, KY

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Photo by Gabriele Romano on Unsplash — representative image for Middlesboro Canal Park

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Middlesboro Canal Park

Middlesboro, KY

Park in Middlesboro, KY

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Things to Do Today in Middlesboro

Long John Silver's

Civic Center Park

Bradner Stadium

Shades of Brown

GOLDEN TICKET CINEMAS MIDDLEBORO 4

Middlesboro Farmer's Market inside Crater City

Middlesboro Community Center

Daniel Boone's Trail

Cumberland Gap Mountain Spring Water

Rally's

DQ Grill & Chill

Save A Lot

The Table Coffee House

Food City

The Pinnacle-Cumberland Gap Tn

Crater City Coffee Company

Fellowship Center

KFC

Pine Mountain State Resort Park

He Hu Darz

Cumberland Gap National Historical Park

Conley's Drive In Restaurant

Gem City Cakes

Beans Fork

Yamato Steakhouse

Dairy Queen

Burger King

Fords Woods Park

Belk

Sonic Drive In (Sonic Drive-In)

Middlesboro Mall

Stinking Creek Knox County

Arby's

Mountain Mugs Craft and Coffee

Pinnacle Overlook Cumberland Gap National Historical Park

Subway

Shillalah Creek Wildlife Management Area

Sagebrush Steakhouse

City Sippers

Kay Jay Recreation Park

Middlesboro (Cracker Barrel)

Saylor Park L Rev

Kroger

Food City Starbucks - Middlesboro, KY

Barbourville City Park

Goody's

Ford's Wood Park

McDonald's

Starbucks

Middlesboro Canal Park

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Today in Nearby Cities