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:
Day One: Arrival and Local Discoveries
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.
Day Two: Local Exploration and Art
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.
Day Three: Outdoor Escapes and Regional Exploration
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.
Day Four: Day Trip to Pine Mountain and Harlan
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.
Day Five: Historical Sites and Local Attractions
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.
Day Six: Wilderness Adventures and Local Delights
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.
Day Seven: Departure and Final Explorations
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!