16 Most Fun Things To Do In Middlesboro, Kentucky

In the scenic embrace of the Appalachian Mountains, you can find the small but lively town of Middlesboro. The city stands as a captivating destination with a rich tapestry of history and a welcoming embrace of natural beauty. 

Middlesboro was founded by Scottish entrepreneur Alexander Arthur in 1886. It boasts a unique claim to fame as one of the only cities in the United States built within a meteor crater and creates a geological wonder that draws visitors from near and far.

This charming city has a population of around 10,000 residents and attracts a steady stream of visitors annually, with its historical significance and diverse range of recreational offerings. 

The Cumberland Gap National Historical Park, home to the famous Cumberland Gap, provides a stunning backdrop for outdoor enthusiasts and offers hiking trails and caves ripe for exploration.

Middlesboro’s historical allure is further accentuated by the Bell County Historical Society Museum, narrating tales of the region’s past, and the Alexander Arthur Museum, dedicated to the city’s founder. 

The city’s vibrant cultural scene is punctuated by the Shawnee Theatre, a local hub for theatrical performances and community arts.

Middlesboro has approximately 200,000 visitors each year and has become a sought-after destination for those seeking a blend of history, nature, and small-town charm. 

The climate, characterized by four distinct seasons, makes Middlesboro an appealing year-round destination. While summers offer warmth and outdoor adventures, the fall season transforms the landscape with vibrant foliage and makes it an ideal time for festivals and events. 

Spring and early autumn provide mild temperatures and offers a comfortable environment for exploring the city’s outdoor and cultural attractions. From outdoor adventures to cultural experiences, Middlesboro has something for everyone. Here are the 16 most fun things to do in this hidden gem of a town.

1. Cumberland Gap National Historical Park

Embark on a journey through history by hiking the trails of the Cumberland Gap National Historical Park. Discover the breathtaking scenery that once served as a gateway to the west for pioneers. With trails of varying difficulty levels, it’s an outdoor enthusiast’s paradise.

Cumberland Gap National Historical Park

Cumberland Gap National Historical Park was established in 1940 and is a treasure trove of history and natural beauty. Its roots date back to the early 19th century, when pioneers and settlers carved their way through the Cumberland Gap, a strategic passage in the Appalachian Mountains. 

This park spans Kentucky, Virginia, and Tennessee, encapsulates the significance of this historic gateway. The park boast over 24,000 acres and offers a diverse landscape of forests, waterfalls, and rugged terrain. 

The famous Pinnacle Overlook provides breathtaking panoramic views, while guided tours through Gap Cave unveil the mysteries beneath the surface. Visitors can step back in time at Hensley Settlement, a preserved mountain community frozen in the early 20th century. 

Cumberland Gap National Historical has rich history and stunning landscapes and remains a testament to the enduring spirit of exploration and westward expansion in the United States.


Middlesboro, KY 40965, United States

2. Daniel Boone Wilderness Trail

The Daniel Boone Wilderness Trail in Middlesboro, Kentucky, was established in 1775. It stands as a historic pathway that played a pivotal role in American frontier history. 

Daniel Boone Wilderness Trail

The trail was named after the legendary frontiersman Daniel Boone and extends for over 200 miles. It marks the route he blazed during the late 18th century to open up the western frontier for settlement.

Boone’s Wilderness Trail is often referred to as the “Wilderness Road,” became a crucial avenue for early pioneers journeying into the untamed territories beyond the Appalachian Mountains. 

Today, the Daniel Boone Wilderness Trail preserves this significant chapter in American history. It allows visitors to follow in the footsteps of the brave pioneers who sought a new life on the frontier. 

The trail offers interpretive sites, educational programs, and a tangible connection to the past and makes it a fascinating destination for history enthusiasts and those eager to explore the roots of westward expansion in the United States.


91 Bartlett Park Road, Middlesboro, KY 40965, United States

3. Bell County Historical Society Museum

Delve into the rich history of the region by visiting the Bell County Historical Society Museum. This museum has artifacts and exhibits to engaging stories and provides a fascinating glimpse into the past.

Bell County Historical Society Museum

The Bell County Historical Society Museum was founded in 1980. It is a captivating repository of the region’s rich heritage. The museum offers visitors a fascinating journey through time. 

The museum is housed in the former First National Bank building, which was constructed in 1897 and itself is a piece of history.

The exhibits within the museum provide insight into Bell County’s diverse past and encompass topics such as Native American history, the impact of coal mining, and the development of the local community. 

The museum artifacts and photographs to engaging displays and serves as a dynamic educational resource for locals and visitors alike.

For history enthusiasts, the Bell County Historical Society Museum is a must-visit destination to explore new things to do in Middlesboro. It offers a comprehensive and accessible glimpse into the cultural tapestry of Middlesboro and its surrounding areas.  

The museum’s commitment to preserving the legacy of Bell County ensures that the stories of the past continue to resonate with present and future generations.


207 N 20th St, Middlesboro, KY 40965, United States

4. Alexander Arthur Museum

Discover the life and legacy of Alexander Arthur, the Scottish entrepreneur who founded Middlesboro. The Alexander Arthur Museum showcases his influence on the town’s development through informative exhibits and displays.

Alexander Arthur Museum

The Alexander Arthur Museum was established in 2002 and serves as a dedicated space to honor and commemorate the life and legacy of the town’s founder, Scottish entrepreneur Alexander Arthur. 

The museum is situated within the historic Carnegie Library building, constructed in 1911 and adds an extra layer of historical significance to the site.

Through engaging exhibits and informative displays, the Alexander Arthur Museum offers visitors a journey into the past and provides insights into the vision and contributions of the man responsible for the establishment of Middlesboro in 1886. 

The museum showcases Arthur’s influence on the town’s development, from its early days to its growth as a thriving community. The museum has artifacts, photographs, and interactive exhibits. 

The Alexander Arthur Museum provides a comprehensive look at the life and times of Middlesboro’s founder and makes it a valuable resource for those interested in the history of this charming Kentucky town. 

Visitors can explore the entrepreneurial spirit that shaped Middlesboro and gain a deeper appreciation for the roots of the community and enjoy some new things to do in Middlesboro.


2215 W Cumberland Ave, Middlesboro, KY 40965, United States

5. Golden Ticket Cinemas Middlesboro 4

Golden Ticket Cinemas Middlesboro 4 was established in 2019. It is a contemporary cinematic destination in Middlesboro, Kentucky and offers locals and visitors an immersive movie-watching experience. 

Golden Ticket Cinemas Middlesboro 4

Situated in the Middlesboro Mall, this state-of-the-art cinema boasts four screens and presents a diverse selection of films for audiences of all ages.

The cinema is equipped with modern amenities, including comfortable seating and top-notch audiovisual technology, ensuring a memorable movie experience. 

Golden Ticket Cinemas Middlesboro 4 caters to the entertainment needs of the community and provides a cozy and family-friendly atmosphere for film enthusiasts.

Not only does this cinema contribute to the local entertainment scene, but it also serves as a social hub, bringing people together for shared cinematic experiences. 

Golden Ticket Cinemas Middlesboro 4 has quickly become a go-to destination for moviegoers seeking a blend of convenience and enjoyment in the heart of Middlesboro.


905 N 12th St Suite 25, Middlesboro, KY 40965, United States

6. Cracker Barrel Old Country Store

The Cracker Barrel Old Country Store was established in 1969 has become a beloved fixture in the community. Nestled off Highway 25E, this iconic establishment offers a unique blend of dining, shopping, and a nostalgic trip down memory lane.

Cracker Barrel Old Country Store

The Cracker Barrel chain was founded by Dan Evins. He envisioned creating a gathering place reminiscent of the old country stores and providing a cozy, Southern-inspired atmosphere. 

The Middlesboro location has been a staple for both locals and travelers, known for its distinctive architecture and signature rocking chairs adorning the front porch.

Inside, guests are treated to a warm, rustic ambiance with décor that pays homage to American heritage. The restaurant offers homestyle cooking with a diverse menu featuring classic comfort food. 

Additionally, the attached country store allows visitors to browse through nostalgic candies, decor items, and unique gifts, capturing the essence of traditional country living. 

The Cracker Barrel Old Country Store has an inviting atmosphere and commitment to hospitality and continues to be a cherished destination for those seeking a taste of Southern charm.


1049 N 12th St, Middlesboro, KY 40965, United States

7. Royal Waffle King

Royal Waffle King has been a go-to spot for locals and visitors seeking delicious breakfast and comfort food. This family-owned eatery was established in 1975 by Bill and Lovie Hodge andhas been serving up hearty meals in a welcoming atmosphere for decades.

Royal Waffle King

The restaurant is known for its diverse menu featuring a variety of waffle creations, along with classic Southern breakfast dishes. From fluffy waffles to savory omelets, Royal Waffle King caters to a wide range of tastes, making it a popular choice for breakfast enthusiasts.

The Hodge family’s commitment to quality ingredients and friendly service has contributed to the enduring popularity of Royal Waffle King. This Middlesboro establishment has become a cherished part of the local dining scene, embodying the spirit of Southern hospitality and good old-fashioned comfort food.


1200 US-25 E, Middlesboro, KY 40965, United States

8. Two Gen Grill

Two Gen Grill was established in Middlesboro, Kentucky in 2005. It is a popular local eatery with a rich history. The restaurant has become a cornerstone of the community, offering a diverse menu that caters to various tastes. 

Two Gen Grill

In its early years, Two Gen Grill quickly gained recognition for its welcoming atmosphere and delicious, homestyle cooking. The grill has roots deeply embedded in Middlesboro and has witnessed the town’s growth and evolution over the years. 

Patrons are drawn not only to the delectable food but also to the establishment’s commitment to fostering a sense of togetherness. Since its inception, Two Gen Grill has stood as a testament to the enduring spirit of local businesses, contributing to the vibrant culinary scene in Middlesboro.


1300 Chichester Ave, Middlesboro, KY 40965, United States

9. Skateworld

Skateworld was founded in Middlesboro, Kentucky in 1982. It is a beloved roller-skating rink with a captivating history. The establishment quickly became a cherished local hotspot, offering a fun and family-friendly environment for residents of all ages. 


Over the years, Skateworld has evolved into a community hub, hosting events, parties, and skating lessons. Its vibrant atmosphere and neon-lit rink have made it a go-to destination for both nostalgic adults and energetic youngsters. 

Skateworld is committed to promoting active recreation and has played a significant role in the local recreational scene. The roller-skating haven has continued to bring joy and entertainment to Middlesboro, creating lasting memories for generations of skaters.


2113 Cumberland Ave, Middlesboro, KY 40965, United States

10. Levitt AMP Middlesboro

Check the town’s event calendar and plan your visit during the Levitt AMP Middlesboro Music Series. This free outdoor concert series features a diverse range of musical genres, providing a lively and entertaining atmosphere.

Levitt AMP Middlesboro

Levitt AMP Middlesboro was established in 2016 and has become a cultural cornerstone in Middlesboro, Kentucky. This free music series, held at Levitt AMP Pop-Up Park, was created to bring the community together through the power of live music. 

Since its inception, the event has featured a diverse range of musical genres, showcasing both local talent and renowned artists. Levitt AMP Middlesboro has not only entertained but also revitalized public spaces, transforming them into vibrant gathering spots. 

Attendees enjoy the outdoor concerts that promote community engagement and cultural diversity. Over the years, this initiative has gained momentum, drawing people from different walks of life to experience the joy of live music under the open sky. 

Levitt AMP Middlesboro continues to contribute to the city’s cultural tapestry and fosters a sense of unity and appreciation for the arts while offering a space to enjoy unique things to do in Middlesboro.


2005 W Cumberland Ave, Middlesboro, KY 40965, United States

11. Oldest House In Middlesboro

The Oldest House in Middlesboro was constructed in 1889 and stands as a historical gem in Middlesboro, Kentucky. This iconic residence holds a special place in the city’s history, reflecting the architectural charm of its time. 

Oldest House In Middlesboro

This house was erected during the late 19th century and has weathered the years, witnessing the evolution of Middlesboro around it. The house boasts distinctive features that showcase the craftsmanship of its builders and the prevailing architectural styles of the era. 

Over its long existence, the Oldest House has been a witness to various events, becoming a silent storyteller of the city’s past. Today, it stands as a living testament to Middlesboro’s rich heritage and offers a glimpse into the lives of those who inhabited it during a bygone era. 

Visitors and locals alike appreciate the Oldest House for its historical significance and the tangible connection it provides to Middlesboro’s roots.


1003 N 19th St, Middlesboro, KY 40965, United States

12. The Palace

The Palace was established in Middlesboro in 1924. It is a historic theater steeped in local culture. This iconic venue has stood the test of time, offering entertainment and enchantment to the community for nearly a century. 

The Palace

The year of its founding marked the beginning of an era that saw the Palace as a focal point for various performances, from silent films to live shows. Over the years, the theater underwent renovations and adaptations, keeping pace with changing times while retaining its architectural charm. 

The Palace has hosted countless memorable events, which makes it a cherished landmark in Middlesboro’s cultural landscape. Its rich history is not only reflected in the ornate detailing of its design but also in the diverse array of performances that have graced its stage. 

The Palace remains a beloved institution that connects generations through the shared experience of entertainment in this historical setting and offers them some charming things to do in Middlesboro.


2008 Cumberland Ave, Middlesboro, KY 40965, United States

13. Cumberland Mountain Fall Festival

If you find yourself in Middlesboro during the fall, don’t miss the Cumberland Mountain Fall Festival. This annual event celebrates the season with live music, food vendors, and family-friendly activities.

Cumberland Mountain Fall Festival

The Cumberland Mountain Fall Festival was established in 1982. It is an annual celebration that has become a beloved tradition in the region. This vibrant festival marks the arrival of autumn with a myriad of activities and attractions for locals and visitors alike. 

Since its inception, the festival has grown in scale and offers a diverse range of events such as live music, arts and crafts exhibitions, food vendors, and family-friendly activities. 

Attendees can enjoy the picturesque setting of Cumberland Mountain as they partake in the festivities. The Fall Festival has become a platform for local artists and businesses to showcase their talents and products and fosters a sense of community pride. 

Over the years, it has evolved into a significant cultural event, drawing people from surrounding areas to experience the charm and hospitality of Middlesboro during the beautiful fall season.


1260 N 12th St, Middlesboro, KY 40965, United States

14. Middlesboro Mall

Middlesboro Mall was established in 1985. It is a key shopping destination with a compelling history. The mall was founded to cater to the retail needs of the local community, providing a centralized space for diverse shopping experiences. 

Middlesboro Mall

Since its inception, Middlesboro Mall has been home to a variety of stores that ranges from well-known national brands to local businesses. Over the years, the mall has undergone changes and renovations, adapting to evolving retail trends. 

It serves as a hub for residents to explore fashion, electronics, and other goods. Middlesboro Mall has also been a venue for community events, contributing to the social fabric of the city. 

Middlesboro Mall has a central location and diverse retail offerings and continues to be a significant part of the local shopping experience, providing convenience and a sense of community for shoppers.


905 N 12th St #1, Middlesboro, KY 40965, United States

15. Shillalah Creek Wildlife Management Area

Shillalah Creek Wildlife Management Area (WMA) was established in 1999 and is a natural treasure with a rich history. The WMA was created to preserve the area’s diverse flora and fauna while providing recreational opportunities for outdoor enthusiasts. 

Shillalah Creek Wildlife Management Area

Shillalah Creek WMA covers a significant expanse and is characterized by its rolling hills, dense forests, and meandering waterways. It offers a picturesque setting for activities like hiking, birdwatching, and hunting in designated seasons. 

The year of its establishment marked a commitment to conservation and responsible land management. The WMA serves as a haven for wildlife and includes various species of birds, mammals, and aquatic life. 

Visitors can explore the designated trails and immerse themselves in the beauty of nature and makes Shillalah Creek WMA a popular destination for both locals and nature enthusiasts seeking a serene escape.


Mill Branch-Hensley Flatts Rd, Middlesboro, KY 40965, United States

16. Downtown Middlesboro

Immerse yourself in the town’s history by taking a stroll through downtown Middlesboro. The historic architecture and landmarks tell the story of Middlesboro’s evolution, offering a glimpse into its past.

Downtown Middlesboro

Downtown Middlesboro was established in the late 19th century and has a rich history and vibrant atmosphere. The downtown area was founded in 1886 and has evolved into a hub of commerce, culture, and community. 

The downtown district is characterized by historic architecture, reflecting the city’s enduring charm. Over the years, it has been a witness to economic fluctuations, cultural shifts, and urban development. 

The establishment of various businesses, shops, and local establishments has contributed to the area’s lively and welcoming ambiance. Downtown Middlesboro has also been a center for community events, fostering a sense of unity among residents. 

Today, visitors can explore the historic streets, enjoy local cuisine, and experience the unique blend of tradition and modernity that defines Downtown Middlesboro.


2008 W Cumberland Ave, Middlesboro, KY 40965, United States


Middlesboro, Kentucky, may be a small town, but it packs a punch when it comes to fun and exciting activities. Whether you’re an outdoor enthusiast, history buff, or just looking for a relaxing getaway, these 16 fun things to do in Middlesboro, KY has something for everyone.