Maybe it’s my small-town roots, but I’ve always been drawn to quaint little towns. There’s something special about strolling down storybook streets that feel like stepping back in time.

Just about 45 minutes from us lies Cumberland Gap. Blink and you might miss it—it sits quietly just before the Tennessee–Kentucky line—but this charming town makes for a perfect day trip. Whether you’re in the mood for a leisurely walk, a relaxed lunch, or a bit of exploration, Cumberland Gap delivers.

One favorite stop is the cozy coffeehouse beside the river, offering pastries and sandwiches. We love grabbing a seat at the Creekside Bistro tables and watching the world go by. You’ll often see students from Lincoln Memorial University coming and going, adding a lively energy to the peaceful setting.

Another great lunch option is Nineteen Nineteen, named for the age of the building itself. The historic charm is unmistakable—squeaky floors and an old storefront layout transport you to another era. Interestingly, the chef relocated here from California, and the result is gourmet comfort food served in a delightfully nostalgic atmosphere.

After lunch, set out to explore. Take a short hike to the Iron Furnace, or challenge yourself with the steeper trail to the Tri-State Peak, where you can stand in Tennessee, Kentucky, and Virginia all at once. Don’t miss the train trestle, the covered bridge walkway leading to Lincoln Memorial University, or the grist mill beside the bed-and-breakfast. In spring, the dogwoods are simply glorious.

Cumberland Gap hosts several street fairs throughout the year, complete with live music and arts and crafts, so be sure to check the town’s website for upcoming events. While it may appear to be a sleepy little town at first glance, it’s actually a vibrant and active community.

You’ll find antique shops, a beautifully refurbished church now serving as a wedding and event venue, and a regular farmers market. On occasion, we even stumble upon hometown musicians gathering for a bit of picking and grinning.

You just never know what treasures you’ll discover in a small historic town just around the corner.