The Best Things To Do In Cumberland Gap, Tennessee

There’s something magnetizing about the Cumberland Gap. This geologic formation involves a deep notch, or “gap,” in the otherwise continuous ridgeline of Cumberland Mountain. The historic passage provided a critical gateway for Native Americans, bison, and more than 300,000 people crossing the Appalachians during the early days of U.S. westward expansion. It later became a strategic outpost for both Union and Confederate troops during the Civil War. The gap, situated near the heart of where Tennessee, Kentucky, and Virginia meet, called to travelers years ago and continues to today.

The town of Cumberland Gap, Tennessee, sits in the valley below this mesmerizing dip, as if gazing up at it in awe. Deep green mountainscapes hug the park-like town in a 360-degree embrace. As it has for eons, Cumberland Gap welcomes “outsiders,” both those appreciating the region’s natural beauty and those visiting from locations near and far. With its proximity to Lincoln Memorial University, the town exudes a youthful vibrance and collegiate population that ensures the welcoming passage documents new and diverse stories for years to come.

When you arrive in Cumberland Gap, expect to hear gentle music wafting over from a nearby porch. Much of the town’s charm revolves around the simplicity of a quality porch-sit, whether recovering from a long hike, enjoying a local band, or listening to the sound of silence.

Where to Stay

With its 1700s log cabin and late 1800s tongue-and-groove wood house, the Olde Mill Inn Bed & Breakfast evokes the sense of respite that westward travelers must have felt upon passing through the mountainous Cumberland Gap into town. Each of its nine rooms are thoughtfully decorated with eclectic themes that feel like home—from Nana’s sunflower room to the rustic Daniel Boone den. In the morning, you can share stories with fellow travelers at the inn’s 18-person, custom-made wooden plank table over a hearty breakfast of quiche, sausage, coffee, and warm blueberry muffins. The building sits beside the clear, babbling Gap Creek, so plan to let its song lull you into a restorative afternoon nap or meditation from the inn’s outdoor patio or your own private porch off The Suite—a two-bedroom rental with a jetted tub for two. 

The town also offers several convenient, peaceful, short-term rentals through Airbnb or Vrbo. You’ll find two unique options on Colwyn Avenue, the main street through Cumberland Gap’s historic downtown. 

One, a craftsman Oklahoma Kit Home built in 1928, has three bedrooms, one bathroom, and delightful vintage furnishing. Located directly across from the town’s Festival Park, outfitted with a shaded porch, and boasting manicured landscaping and cheerful yellow paint, it’s the best place in town to sit for a spell and enjoy your sweet tea. 

The other is a suite, the Inn Over Angelo’s, which rests above a local Italian joint that offers in-room dining. Your stay in this 1890 property includes antique mahogany trim, cherry wood flooring, hand-carved fireplace mantels, exposed brick walls, views of town, and maybe even a ghost story or two.

Where to Eat

Begin at The Juice Spot, a casual dining option hosted in an old wedding chapel, for a smoothie, fresh-pressed juice, or acai bowl. Aptly named, The Day Starter—pineapple, banana, spinach, agave, and coconut water—will help power you up the mountain for your afternoon hike. You can also grab homemade wraps or salads to-go for a picnic later on.

When you’re jonesing for a caffeine kick or a lunch made for lingering, head over to Gap Creek Coffee House, where a sign above the building’s pillow-laden porch swing proudly declares, “The Porch: Sit. Relax. Gossip.” This understated dining nook sits in the shade of a towering mulberry tree. Its seating options sprawl from inside tables to chairs on the porch and outside around the cafe’s grassy side to the peaceful banks of Gap Creek. Grab a book from its adjacent tiny library to read while enjoying a grilled cheese with blackberry jam and jalapeños and local-favorite latte, the Caramel Monkey Monkey—a vanilla-caramel blend.

For a laid-back dinner with friends, plan for a night at Angelo’s in the Gap. You’ll find all your Italian favorites, from fettuccine alfredo and meat lasagna to calzones and pizza. Ample seating inside and on the patio makes this an excellent spot for groups. Pro tip: Opt for the Sicilian deep dish crust to experience the glory of a pizza encircled with perfectly doughy breadsticks.

Nineteen19 Grill & Bar offers diverse lunch and dinner menus in an approachable, yet elegant atmosphere. It’s perfect for a romantic date night, family get-together, or celebratory gathering of friends. You’ll find meals that sample cultures from around the world and just down the street, including tacos, sushi, surf and turf, chicken and waffles, salads, and more. Wherever your entree travels, start with the sweet corn croquettes with jalapeño and roasted garlic lime aioli and end with the berry-topped creme brulee.

What to Do

Despite its small town population and tranquil vibe, Cumberland Gap is filled with activities that may just keep you from that full-day porch nap you had planned. 

Get Outside

Cumberland Gap National Historical Park encompasses 14,000 acres of wilderness with 85 miles of trails, several of which are accessible via a quick walk from your lodging’s front door. A visit to Cumberland Gap truly puts the national park in your backyard.

Start at the Iron Furnace Parking Area and walk the Tennessee Road Trail 0.1 miles to the remnants of an 1819 blast furnace, which produced around three tons of iron each day throughout the 1800s. Follow the trail another 0.3 miles to its intersection with the Wilderness Trail. Turn left to hike another 0.3 miles up the trail to the historic Cumberland Gap formation, noted by a wooden park sign. From here, turn left to hike up Tri-State Peak Trail 0.6 miles to Tri-State Point, where you’ll find an overlook, signage, and a chance to stand in three states at the same time: Tennessee, Virginia, and Kentucky.

Descend Tri-State Point the same way you came up. When you reach the historic Cumberland Gap, turn right on the Wilderness Trail. In about 0.5 miles, you’ll reach a 0.1-mile spur trail to your left where you can check out the entrance to Gap Cave. From that junction, it’s another 0.3 miles to a path that turns to the right that will bring you to the Daniel Boone Visitor Information Center. If you turn right in this parking area, you’ll find a long boardwalk back into town. This hiking loop is about three miles and offers scenery, history, and fresh air to start your day.

If you have time, drive into the park to check out Pinnacles Overlook, which offers a gorgeous view of the town tucked below. Use it to eye good porches for your post-hike refreshment. You can also ask local business owners about the town’s bike rental program to cruise the town’s paved rail-trail greenway.

Shop Local

Cumberland Gap is peppered with local businesses where you can find your own little slice of the town to take home as a memory. Hillfolk is an Appalachian herbal shop and learning space with teas, oils, tinctures, face creams, salves, soaps, books, arts, and more. Stop by for an education on the area’s healing diversity of plants. Meanwhile, antiquers will love the town’s two vintage shops: Whistle Stop Antiques and Gertie's Commissary. The latter is located in Cumberland Gap’s historic depot.

Set aside ample time to peruse the Frame Shop & Gallery for a variety of regional art and photography with a side of local lore from the store’s owner, Steve Moore, born and raised in the region. The nearby Cumberland Gap Artists’ Co-op is another must-stop for Appalachian arts and crafts. You’ll find everything from felted portraits and watercolor landscapes to handmade jewelry and homemade preserves. Chat with the day’s cashier to learn about which of the artworks in the store are theirs and the inspiration they gain from their surroundings.

Explore Town Gems

Take a stroll around Cumberland Gap and you’ll see how the town has melded new with old. Drop a letter to a loved one at the Cumberland Gap Post Office, an adorable hut of a building that was established in 1803. It changed hands between the area’s three states before finding its forever home back in Claiborne County, Tennessee, in October 1885.

Next, head up the road to the Cumberland Gap City Hall, a two-story, red-brick building that was originally constructed in 1925 as the town’s public school. Stop to enjoy the swings out front before looping back to town past The Olde Church Events Center.

Established in 1890, The Olde Church was nearing collapse when a husband-and-wife team, Bill and Tammy, were traveling through Cumberland Gap in 2021 from Oregon. The moment Tammy arrived in Cumberland Gap, she said she felt at home. Within days of seeing the historic church building, the couple bought it and began a major renovation to bring it back to life. As they began their work, Tammy learned how seven generations ago, one of her relatives had entered Tennessee through the area’s famed gateway to the West around 1790. Stop in to hear tales from Tammy and Bill about their intricate rehabilitation project, gaze at colorful light through the church’s original stained glass, or attend one its community events. The space also offers lodging perfect for wedding parties, family reunions, or other groups.

Finish your loop of town with a couple of its newer additions. The Little Congress Bicycle Museum is a quirky, hole-in-the-wall homage to pedal power. The Paul V. Hamilton Center for the Arts is home of LMU’s Arts in the Gap programs, including workshops, exhibitions, and performances rooted in Appalachian crafts. 

You can also opt for an evening ghost tour to see where the past still haunts the present in this quaint little town.

When to Visit

Cumberland Gap is a delightful destination year-round. If you’re looking for a quieter time to visit, choose months when the neighboring LMU is out of session. The fall is also a beautiful time to explore when colorful leaves paint the mountainsides. As a bonus, the autumn scenery in Cumberland Gap comes with far fewer crowds and ample parking compared to the region's well-known leaf-peeping spot, Great Smoky Mountains National Park.

If you want to soak up Cumberland Gap at its liveliest, plan your trip around one of its many annual festivals. FolkFest occurs in August and celebrates Appalachian crafts, music, vendors, and more, with some of the event’s most popular concerts taking place on residents’ porches. The Tri-State Outdoors Fest takes place in July and showcases Cumberland Gap’s rich culture of hiking, mountain biking, paddling, hunting, fishing, boating, and other outdoor activities. Other events include outdoor movies, farm-to-table dinners, Airstream rallies, and more. You can learn about the town’s upcoming events on its website.