7 Places You Must Visit in Cumberland Gap

The historic town of Cumberland Gap is nestled at the foot of the Cumberland Mountains and known by many as the “Gateway to the West.” Rich with history and natural beauty, Cumberland Gap makes for the perfect outdoor getaway. Located within the downtown area, you will find an array of little shops, restaurants, and even a bicycle museum. To help plan a day in Cumberland Gap, we’ve highlighted the top seven ways to experience this small mountain town.


1. Cumberland Gap National Historic Park

Cumberland Gap’s National Historical Park is loaded with American Indian, early pioneer, and Civil War history. Daniel Boone even passed through the gap in the mid 1700’s while leading a team of frontiersman to Kentucky. The park offers visitors 70 miles of trails to explore and camp, as well as tours of the historic Hensley settlement. 


2. Little Congress Bicycle Museum

This bicycle museum is a must-see if you visit Cumberland Gap. Along with the rest of the town, the museum is full of history including the 1895 Penny Farthing, which is the oldest bicycle on display. One of the most exotic bicycles you’ll also see is the 1934 quadrocycle, which sat four people and was used as a pacer vehicle in the six-day bicycle races of the Great Depression. Admission to the museum is free but visitors are encouraged to contribute to the donation box at the front door. 


3. The Olde Mill Inn Bed and Breakfast

After a long day of exploring what Cumberland Gap has to offer, have a stay at the Olde Mill Inn Bed and Breakfast and sleep in 1700’s cabin or a Victorian Canopy bed. A delicious breakfast is served to guests every morning on a 20-ft plank table. The Inn is also located just 200 yards away from the Tri- State Peak Trail head, so once your breakfast settles, make sure to check that out.


3. Tri-State Peak Trail

With Cumberland Gap being at the junction of Kentucky, Virginia, and Tennessee, the Tri- State Peak Trail is commonly known as the “saddle” of the gap. The 2.2 mile trail, which was once used by the first settlers of Kentucky, gradually leads hikers to an elevation of 1,798 feet and boasts an incredible view from the top.

5.  Pineapple Tea Room

Once you’ve worked up an appetite from hiking, grab a coffee or a bite to eat at the Pineapple Tea Room. This cozy little restaurant is the perfect place to kick back and relax while enjoying a great meal. The perfect atmosphere has created a popular hangout and study spot for college students from the nearby Lincoln Memorial University.

6. Mitty’s Metal Art

Have you ever had the chance to watch a professional blacksmith at work? Stop by Mitty’s Metal Art Studio in downtown, and mark that off your list. While there, step back in time and watch professional blacksmith Ryan Schmidt create sculptures, furniture, and commissioned works of art for customers. You can even purchase a few of Ryan’s most popular pieces from the collection.

7. The Pinnacle Pub

After a long day of exploring the historic town of Cumberland Gap, stop by the Pinnacle Pub and grab a cold drink with some stalwart pub food such as wings, burgers, wraps, and pretzels with beer cheese. This local hangout has everything you need for a good time including a jukebox, pool tables, and dart boards.

For information on the Town of Cumberland Gap, visit townofcumberlandgap.com.

Written by Trevor Rice for Northeast Tennessee Tourism.

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