Plan your Visit: Daytrippin’ or a Weekend Away


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

-Start with breakfast and a drink at Gap Creek Coffee House.

-Then visit the Little Congress Bicycle Museum (pick up a town map)

-Stop in the Olde Mill Bed and Breakfast (ask if they will show you around)

-The Iron Furnace, within the Cumberland Gap National Historical Park is a short walk from this location. 

-Come back by Gertie’s Commissary and visit where Wolfwell got its start. 

-Maybe grab lunch…Angelo’s, Nineteen19 or Gap Creek Coffee

-Dessert at Flour Baby’s and Music at Papa Chum’s

-Stop by the Post Office and mail a postcard or just say Hello to Cindy (tell her we sent you – if you have ever ordered from us, more than likely she has handled your package)

-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.

-The Artist Co-Op is on Colwyn, featuring local art. 

-Wander on up Colwyn and stop in Whistle Stop Antiques

 -Stop in at The Frame Shop and Gallery and ask Steve about framing your best image from the visit or pick up a piece in the gallery (ask about taking a picture with his truck… a local icon!)

-Walk up to the Olde Church, an event center, and take a photo. 

-Come down by City Hall and take a moment to enjoy the swings and the view.

-Enjoy the Boone Greenway up the wooden trail (UPHILL) to the Cumberland Gap National Historical Park or walk towards (FLAT and EASY) the campus of Lincoln Memorial University and enjoy the covered bridges and railroad tunnel. 

-Don’t forget to grab something to eat and make plans to return before you leave town. 

-If you have time, make plans (ahead of your visit) for a ghost tour!

-See y’all again soon!


A Weekend Trip


4:00pm Check In 

-several local accommodations in Cumberland Gap, and maybe an early check in if you ask

-Stop in The Little Congress Bicycle Museum and pick up a town map

-Take a short walk up the Boone Greenway

-Pick a spot for dinner, lots of choices

-Save room for dessert and/or a nightcap

-Up for a ghost tour, be sure to make plans in advance

-Stop by Buerkau Park and enjoy the sounds of the creek at night



-If breakfast isn’t available at your lodging, you can always grab it at Gap Creek Coffee 

-You might want to get a to-go meal for the trails at any of the local eateries

-A trail for every level…pick the one perfect for you. Also, remember each trail has beautiful scenery to enjoy. Take lots of photos and tag us. 

-If you didn’t pack a meal, now is time to visit one of the eateries in town. several  local accommodations in Cumberland Gap

-Save time to wonder around town and visit the local shops, especially Wolfwell at Gertie’s 

-Treat yourself to a cookie (Flour Baby’s), some vinyl (Papa Chum’s) and blacksmithing (Mitty’s Metal)

-More than likely there is also an event happening, sometime over the weekend. Take time to ENJOY!

-Stop by the Frame Shop and ask Steve about framing your favorite photo from your visit. 

-Visit the Iron Furnace at the Cumberland Gap National Park, a short walk from the Olde Mill Inn Bed and Breakfast. 

-Dinner…it is always a good idea to try out all of the Gap eateries, or if you are like us, do a tasting round. Whatever you decide, we guarantee you will not leave town hungry.

-Take a stroll down Colwyn Avenue or walk Boone Greenway (especially towards the tunnel) and look for the deer. 



-Sleep in…you deserve it!

-after you pack up grab a bite to eat before you head out of town

-Take a moment to visit The Olde Church in Cumberland Gap(an event space) and snap a photo(wonderful backdrop)

-One last look around for any items you forgot to purchase or thought about overnight

-Now…three choices…how are you leaving town? 

-Kentucky: Visit Pine Mountain State Park and take a photo at the Chained Rock. 

-Tennessee: Visit the Abraham Lincoln Library and Museum on the campus of Lincoln Memorial University. Don’t rub Abe’s nose! 

-Virginia: Visit Wilderness Road State Park and ask about the Ely House (now known as Karlan)

-For everyone….If you have an opportunity, drive, or hike if you are up to that, to the Pinnacle Overlook at the Cumberland Gap National Historical Park. That view is breathtaking!

Safe Travels and we hope to see you again soon! 


In the Gap

522 Colwyn Avenue

Angelo’s in the Gap

Boone Greenway

Caboose Saloon

Cumberland Gap Artists’ Co-Op

Cumberland Gap City Hall

Cumberland Gap Inn

Cumberland Gap Post Office

Cumberland Gap Wedding Chapel

Frame Shop and Art Gallery

Flour Baby’s Bakery

Gap Creek Coffee House

Inn over Angelo’s

Iron Furnace

Kaitlyn DeVries Memorial Dog Park

Lincoln Memorial University Arts in the Gap

Little Congress Bicycle Museum

Mitty’s Metal

Nineteen19 Grill and Bar

Olde Church in Cumberland Gap

Olde Mill Inn Bed and Breakfast

Olde Towne Cumberland Gap Ghosts Tours

Papa Chum’s Music

Whistle Stop Antiques



Bell County Historical Society and Museum 207 N 20th Street Middlesboro, KY 40965

Bell County Tourism (KY)

Conley’s Drive Inn 1693 Cumberland Avenue Middlesboro, KY 40965

Cumberland Gap National Historical Park

Harlan County Tourism 201 S. Main Street Harlan, KY 40831

Ike’s Artisan Pizza 2020 Cumberland Avenue Middlesboro, KY 40965

Lazy River Kayak and Tubing 318 US-119 Pineville, KY 40977

Main Street Middlesboro 2008 W. Cumberland Avenue Middlesboro, KY 40965

Main Street Pineville 300 W. Virginia Avenue Middlesboro, KY 40977

Middlesboro Country Club 155 Country Club Lane Middlesboro, KY 40965

Pine Mountain State Park 1050 State Park Rd, Pineville, KY 40977

Portal 31 Lynch 100 Church Street Lynch, KY 40855

Portal Pizza 101 N. Main Street Harlan, KY 40831

Sassy Trash 108 N. Main Street Harlan, KY 40831

Shades Cafe 2119 Cumberland Avenue Middlesboro, KY 40965



Abraham Lincoln Library and Museum 120 Mars-Debusk Pkwy, Harrogate, TN 37752

Claiborne County Tourism (TN) 1740 Main Street 37879

Frosty Mug

Heavy’s on the River Kayak and Tubing 125 Benfield Ln, Harrogate, TN 37752

Lincoln Memorial University 6965 Cumberland Gap Pkwy, Harrogate, TN 37752

Woodlake Lodge and Golf Course 330 Woodlake Blvd, Tazewell, TN 37879



Dutch Treat 133 Deroyal Industries Rd, Rose Hill, VA 24281

Lee County Tourism

Wilderness Road State Park


Remember the most important thing is to plan a visit to Cumberland Gap ASAP.

We will be here, waitin’ on y’all.