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After the successful completion of the State of Tennessee’s 2-year “Tennessee Downtowns” program, the town of Cumberland Gap, Tennessee has launched its new tourism brand and website. The new branding
So much to offer in such a quaint place. Cumberland Gap has something for everyone. The Gap is basically a day’s drive from half of the United States population. Cumberland Gap can be enjoyed in a day, a weekend or a lifetime. We have provided a list of resources and links at the bottom of this page. Of course, if you are visiting the town we have several options, which are listed below.
A Day Trip
A Weekend Trip
A Week Long Visit
Explore Cumberland Gap: A Week-Long Itinerary
Embark on an unforgettable journey through Cumberland Gap—a town steeped in history, surrounded by breathtaking natural beauty, and filled with warm Southern hospitality. Whether you’re a history enthusiast, outdoor adventurer, or simply seeking a tranquil getaway, Cumberland Gap offers something special for everyone. Here’s a detailed itinerary to help you make the most of your week-long stay:
Accommodations and Local History
Upon arrival, settle into one of Cumberland Gap’s charming accommodations. Options range from traditional properties to cozy bed and breakfasts and unique short-term rentals. Pro tip: Ask about early check-in—hospitality is a hallmark here, and they’ll accommodate if possible.
Local Museums and Exploration
Start your exploration at the Little Congress Bicycle Museum, where Ralph shares his impressive private collection with visitors. Don’t forget to pick up a town map—it’ll prove invaluable during your stay. Next door, at the Olde Mill Bed and Breakfast, Kim can provide a tour steeped in local history.
Exploring the Outdoors
Afterwards, take a leisurely stroll to the Iron Furnace within Cumberland Gap National Historical Park. Capture stunning photos of this historic site, but remember, climbing the structure is strictly prohibited. Alternatively, enjoy a peaceful walk along the Boone Greenway, starting from Gap Creek Coffee’s covered bridge and ending at Lincoln Memorial University.
Dining and Evening Relaxation
For supper, indulge in local cuisine at one of the many eateries within walking distance of your accommodation. After dinner, take a twilight stroll through town—perhaps you’ll even meet the town mayor, enjoying a cigar under the stars.
Morning Energies
Start your day with a delicious breakfast at Gap Creek Coffee House or The Juice Spot. Armed with your map, head to City Hall to say hello to Linda and enjoy the swings overlooking town—once a schoolyard, now a scenic spot.
Art and Culture
Continue your journey at The Frame Shop and Gallery, where Steve’s expertise in framing local art shines. Visit Whistle Stop Antiques in the old Shell Station building for a glimpse into Cumberland Gap’s past.
Historical Landmarks and Local Businesses
Gaze up at the Olde Church, now a vibrant event center saved by dedicated locals. Stop by the Olde Wedding Chapel, home to The Juice Spot’s drinks and snacks.
Shopping and Local Gems
Browse the Artist’s Co-Op on Colwyn Avenue for locally crafted art and visit HillFolk for herbal delights. Don’t miss 522 Colwyn, a historic 1928 Oklahoma Kit Home available for short-term rental.
Dining and Nightlife
Lunch options abound—try Angelo’s in the Gap or the eclectic menu at Nineteen19. Drop by Gertie’s Commissary, where Wolfwell began, and explore Cumberland Gap Spring Water’s source at Gap Creek.
Evening Activities
Consider a haircut at Singler’s Barber Shop on Brooklyn before dinner and plan ahead for a ghost tour—an eerie end to your evening adventure.
Exploring the Outdoors
Enjoy breakfast before heading to Cumberland Gap National Historical Park Visitor Center. Consult with park rangers for trail recommendations suitable for your interests and abilities. Don’t miss the panoramic view from Pinnacle Overlook before departing.
Regional Museums and Cultural Stops
Cross into Bell County for a visit to Bell County Historical Library and Museum—an essential stop for history buffs. Enjoy local eateries like Conley’s Drive-In and Crater City Coffee in nearby Middlesboro.
Shopping and Cultural Exploration
Shop at the Emporium at 2120 Cumberland Avenue for unique finds before returning to Cumberland Gap.
Pine Mountain Adventures
Begin at Pine Mountain State Park’s lodge for stunning views and a hearty meal. Capture photos at Chained Rock, known for its intriguing legend.
Harlan County Excursions
Explore Harlan’s Sassy Trash for shopping and Moonbow for coffee. Enjoy eats at the Portal or Harlan County Beer. Consider zip-lining or ATV trails at Harlan County’s Portal 31.
Scenic Return
Take the scenic route back to Cumberland Gap through Virginia, enjoying the picturesque landscapes along the way.
Educational and Cultural Stops
Visit the Abraham Lincoln Library and Museum at Lincoln Memorial University for a comprehensive look at local history. Explore the campus and learn about the Arts in the Gap program from Grace.
Outdoor Activities
Consider kayaking or tubing at Lazy River Kayak or Heavy’s, or axe throwing at Shelly Belle’s.
Local Cuisine and Exploration
Drive down Powell Valley to visit Speedwell Academy and enjoy a meal at Frosty Mug in Harrogate Park.
Wilderness Road State Park
Experience Martin’s Station and the Ely House at Wilderness Road State Park’s outdoor living history museum. Explore the Wilderness Road Trail linking to Cumberland Gap National Historical Park.
Lee County Exploration
Visit Dutch Treat for a gourmet sandwich and explore the area’s scenic backroads.
Morning Relaxation
Enjoy breakfast by Gap Creek and take a final stroll through town, looking for deer and sharing memories.
Last-Minute Shopping and Departure
Pick up any last-minute items before departing, and consider staying for lunch at a favorite local restaurant.
Local Attractions and Options
Consider golfing at Middlesboro Golf Course or exploring nearby attractions like Hatfield Knob in Campbell County.
Plan Your Visit Today
Cumberland Gap invites you to embark on a week-long adventure filled with history, outdoor exploration, and local charm. Start planning your visit to this hidden gem and discover why Cumberland Gap is a destination you’ll want to return to time and again.
See Y’all Soon!
As you bid farewell to Cumberland Gap, know that this welcoming town eagerly awaits your return. Whether you’re drawn by its historical landmarks, scenic trails, or friendly locals, Cumberland Gap promises a memorable getaway for all. Safe travels, and see y’all soon!
A Weekend Getaway in Cumberland Gap: Where History and Adventure Await
Cumberland Gap, a quaint town nestled amidst rolling hills and rich history, beckons travelers seeking a weekend escape. Whether you’re drawn by its historical significance, outdoor adventures, or charming local culture, Cumberland Gap promises a memorable experience from Friday evening to Sunday afternoon. Here’s a detailed itinerary to make the most of your visit:
Start your weekend getaway by checking into one of Cumberland Gap’s cozy accommodations. Many places offer early check-ins if requested, ensuring you can settle in and unwind right away.
Explore Local History and Charm
After settling in, head over to The Little Congress Bicycle Museum. Here, you can delve into the town’s past while picking up a handy town map to guide your explorations.
Evening Stroll on the Boone Greenway
Take a leisurely walk along the Boone Greenway, soaking in the tranquil evening ambiance and perhaps spotting local wildlife amidst the lush greenery.
Dining and Nightlife
As night falls, indulge in a delicious dinner at one of Cumberland Gap’s many dining options. Whether you’re craving Southern comfort food, international cuisine, or a casual bite, the town offers plenty to satisfy every palate. Save room for dessert or a nightcap to cap off your evening.
Ghost Tour and Local Delights
For those intrigued by the paranormal, plan ahead and book a ghost tour—a spine-tingling experience that adds an extra layer of excitement to your night in Cumberland Gap. Before calling it a night, unwind at Buerkau Park, where the gentle sounds of the creek provide the perfect backdrop for relaxation.
Morning Energies
Start your Saturday with a hearty breakfast, either at your lodging or at local favorites like Gap Creek Coffee or The Juice Spot.
Gear Up for Outdoor Fun
Prepare for a day of outdoor adventure by grabbing a to-go meal from one of Cumberland Gap’s eateries. With trails catering to all levels of hikers, you’re sure to find one that suits your pace. Remember to capture the scenic beauty with plenty of photos to share and tag your experience.
Local Gems and Shopping
After your hike, swing by Gertie’s Commissary, where WolfWell began, and explore its unique offerings. For lunch, consider dining at Angelo’s, Nineteen19, or returning to Gap Creek Coffee for a satisfying meal.
Shopping and Local Art
Visit The Nutty Squirrel Trading Post for souvenirs or the Iron Furnace Tattoo Company for a more permanent memento. Need a grooming session? Singler’s Barber Shop on Brooklyn is a local favorite.
Explore Local Culture
Stay at 522 Colwyn, a charming VRBO in a historic 1928 Oklahoma Kit Home with Festival Park just across the street. Browse local art at The Artist Co-Op and don’t miss Hillfolk! at the back. Wander further to Whistle Stop Antiques and The Frame Shop, where Steve can help you frame a favorite photo or pick up a piece of local art.
Historical Exploration
Venture to the Iron Furnace at Cumberland Gap National Park, a short walk from the Olde Mill Inn Bed and Breakfast, to delve into the region’s industrial past and natural beauty.
Evening Indulgences
Dinner offers another chance to savor the diverse culinary scene in Cumberland Gap. Whether you opt for a tasting round or settle on a single eatery, you’ll leave satisfied and full of local flavors.
Lazy Morning
On your final day, treat yourself to a well-deserved lie-in. Enjoy a leisurely breakfast before packing up for your departure.
Cultural Stops and Last-Minute Shopping
Before leaving town, visit The Olde Church in Cumberland Gap for a memorable photo op. Take a final stroll to pick up any last-minute souvenirs or gifts you may have overlooked.
Departure and Beyond
As you bid farewell to Cumberland Gap, consider a stop at the Abraham Lincoln Library and Museum on the campus of Lincoln Memorial University, where history buffs can explore artifacts and stories of one of America’s greatest presidents—just remember not to rub Abe’s nose!
Safe Travels and Future Plans
Whether you’re headed to nearby state parks in Kentucky, Tennessee, or Virginia, Cumberland Gap wishes you safe travels. We look forward to welcoming you back soon for more adventures and discoveries.
Plan Your Visit Today
In conclusion, Cumberland Gap offers a perfect blend of history, outdoor activities, and local charm for a weekend getaway. Plan your visit soon to experience all that this hidden gem has to offer. From scenic trails to cultural hotspots and delightful dining, Cumberland Gap awaits your exploration. See y’all soon!
Exploring Cumberland Gap: A Day of Adventure and Charm
Nestled in the picturesque Cumberland Gap region lies a hidden gem waiting to be discovered. If you’re seeking a blend of history, culture, and local charm, look no further than a day trip through this quaint town. Let’s embark on a journey to uncover the highlights and must-visit spots that make Cumberland Gap a destination worth visiting.
Morning Delights at Gap Creek Coffee House
Start your day right with a hearty breakfast and a freshly brewed coffee at Gap Creek Coffee House. This local favorite not only serves up delicious treats but also sets the perfect tone for a day of exploration ahead.
Pedaling Through History: Little Congress Bicycle Museum
After fueling up, head over to the Little Congress Bicycle Museum. Here, amidst a collection of vintage bicycles and cycling memorabilia, you’ll gain insights into the town’s rich history. Don’t forget to grab a town map—they’re available here to guide you through your adventure.
Historical Gems and Hospitality: Olde Mill Bed and Breakfast
Just a short stroll away lies the Olde Mill Bed and Breakfast, where you can immerse yourself in both comfort and history. Ask if they’ll give you a tour—their hospitality and insights into local life will surely enrich your visit.
Exploring Cumberland Gap National Historical Park
A must-see attraction nearby is the Iron Furnace, located within the Cumberland Gap National Historical Park. A short walk from the bed and breakfast, it offers a glimpse into the region’s industrial past and scenic natural beauty.
Local Flavors and Hidden Gems
On your way back, make a pit stop at Gertie’s Commissary, where WolfWell first took root. It’s a perfect opportunity to soak in the local ambiance and maybe pick up a unique souvenir.
Stop by the Post Office and mail a postcard or just say Hello to Cindy (tell her we sent you). Oh and next door is 522 Colwyn, a local VRBO in a 1928 Oklahoma Kit Home, with the perfect front porch and Festival Park across the street.
Lunch and Leisure
If hunger strikes around midday, consider dining at Angelo’s, Nineteen19, or returning to Gap Creek Coffee for a relaxed lunch experience.
Shopping and Souvenirs
No visit is complete without a visit to The Nutty Squirrel Trading Post, offering flags and other mementos of your trip. For something more permanent, drop by the Iron Furnace Tattoo Company. Need a quick haircut? Singler’s Barbershop is just around the corner.
Local Art and Culture
Explore the Artist Co-Op on Colwyn Avenue, showcasing works by local artists. Wander further to Whistle Stop Antiques and The Frame Shop and Gallery, where you can frame memories of your visit or pick up a piece of local art.
Historic Landmarks and Scenic Views
Don’t miss the Olde Church, now an event center perfect for a photo op. Nearby, City Hall offers swings and a scenic view to enjoy a moment of relaxation.
Nature Walks and Scenic Trails
For nature enthusiasts, the Boone Greenway offers both uphill trails leading to Cumberland Gap National Historical Park and flat, easy walks towards Lincoln Memorial University’s campus. Covered bridges and a historic railroad tunnel await your exploration.
Planning Your Return
Before leaving, indulge in a final meal and start planning your next visit. Consider arranging a ghost tour in advance for a thrilling experience on your next trip.
Farewell to Cumberland Gap
As you say goodbye to this charming town, remember to take with you the warmth of its hospitality and the memories of a day well spent. Whether you’re a history buff, art enthusiast, or nature lover, Cumberland Gap welcomes you with open arms—and promises even more to discover upon your return.
Plan Your Visit Today
In conclusion, Cumberland Gap beckons with its blend of history, culture, and natural beauty. Whether you’re planning a day trip or a longer stay, this town offers a unique experience that’s sure to leave a lasting impression. Start planning your visit today and discover why Cumberland Gap is a destination worth returning to time and again.
Until Next Time
Until we meet again, Cumberland Gap will be eagerly awaiting your return. Remember, there’s always more to explore and enjoy in this delightful corner of the world. Safe travels, and see y’all again soon!