Plan your Visit: A Week in Cumberland Gap


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 Week Long Visit

Day One


-Several options in town to stay during your visit, including a traditional property, several short term rentals and a bed and breakfast. Ask about checking in early. Hospitality is a characteristic of the Gap. If they can, they will.

-Once you are settled, stop in the Little Congress Bicycle Museum. A great private collection that Ralph shares with visitors. Be sure to pick up a copy of a town map here. It will serve you well during your visit. 

-Next door to the bicycle museum is the Olde Mill Bed and Breakfast. Stop in and ask Kim for a tour and a bit of history. 

-If you need a quick meal and/or drink there are several choices near you, all within a block of the bicycle museum. 

-Since it might be later in the afternoon and you might be tired from sitting so much on your journey, take a walk. We suggest two locations (both a must during your stay). The Iron Furnace at the Cumberland Gap National Historical Park is the remains of one of the furnaces that once existed in the area. Take some amazing photos, just remember not to climb the structure (park property..BIG NO NO!). While at the furnace enjoy some time at (or in) Gap Creek. This water comes from Gap Cave and is always just right. Our other suggestion is the Boone Greenway (starts behind Gap Creek Coffee on the covered bridge and takes you over two repurposed railroad bridges and through a railroad tunnel (with lighting all along the way) to the campus of Lincoln Memorial University. 

-For Supper (dinner in the South) again, you know the drill…several eateries, all within walking distance of your accommodations. 

-Before bed enjoy a stroll through the town, odds are you will run into the town Mayor smoking a cigar. Say hello to him!

-Get some rest, because tomorrow is a full day.


Day Two

-Good Morning (or afternoon)! If your accommodations do not provide breakfast, head over to Gap Creek Coffee House (opens at 8am) and enjoy breakfast. It is served there until 11am, daily.

-Now with a trusty map in hand, let’s get y’all familiar with town.  We are gonna start at City Hall. Stop in and say hello to Linda, but be sure to enjoy the swings out front. They are there because at one time City Hall was the town school. The view from the swings is NICE!.

-Next stop The Frame Shop and Gallery. Steve has an amazing selection and is beyond talented at this craft. 

-Stop by Whistle Stop Antiques, housed in the old Shell Station building, to take a moment to reminisce about what grandma had. 

-As you look up toward the Pinnacle, you will see the Olde Church, which is now an event center. Stop in and say hello to Tammy and Bill. They have saved this 19th century structure from collapse. 

-The large greenspace in town was the site of the Morrison Home. Currently a greenspace that the town is working to develop into a multipurpose center. 

-Back on Colwyn is the Artist’s Co-Op. Local art for your purchase. 

-522 Colwyn is an Oklahoma Kit Home, built in 1928. The house is also a short term rental. One of the many examples of historic architecture throughout the area. 

– Cumberland Gap Post Office has been in KY, TN and VA. Now in TN, 37724, it’s the place to drop a postcard home to someone or yourself. 

-Across the street is Angelo’s in the Gap. Lasagna and pizza are personal favorites. One of the favorite local bars. Tell Kevin we said hello. 

-Lincoln Memorial University is part of this town. They have the convention center on the corner, but more importantly the Art’s in the Gap program. Grace can tell you all about it. 

-Nineteen19, the newest eatery in town, has an eclectic menu to offer guests. Say hello to the members of the family, Jacqui, Chrstina, Jo, Bernie and Edward. 

-Gertie’s Commissary is where Wolfwell started. Stop in and enjoy everything they offer, but make certain to check out THE CORNER.

-Gap Creek runs through this section of town and is the source for Cumberland Gap Spring Water bottled in Middlesboro. 

-Around the corner is Gap Creek Coffee House, stop in and get a cup of joe from Joe. 

-Outback you will see part of the Boone Greenway…a perfect walk with lighting if you decide to do it later. 

-Mitty’s Metal is on this street before you get to the LMU Art Gallery, stop in and see both. 

-In front of you now is Papa Chum’s (the place locally for vinyl and a ukulele lesson) and Four Baby’s (have the Lemon Cookies!)

-Of course, remember to eat and drink! 

-Ghost Tours are available in town, so make sure to make those plans in advance. 

-After the ghost tour sleep tight!


Day Three

-Now it’s time for some out of town options. Our thoughts of the perfect day are to grab breakfast, order a picnic meal to take with you and head off to the Cumberland Gap National Historical Park Visitor Center. Ask for suggestions from the Park Rangers about suggested trails that best fit you. Before you leave, take a drive up to the Pinnacle Overlook. A short, paved walk out to an amazing view. Be sure to wave at the town of Cumberland Gap from this place. I guarantee we are waving back, you just don’t see us. 

-Bell County Historical Library and Museum is a must on that side of the tunnel for the history buff. An amazing collection of artifacts. If you are fortunate enough, a local author or historian will be on hand to tell a tale or two. Also, ask about area walking and driving tours. 

-Since you are familiar with Middlesboro, be sure to check out some of our favorite local spots to grab a bite in the ‘boro, Conley’s Drive-In, Shades Cafe and Ike’s Pizza. 


Day Four

Pine Mountain State Park, Pineville and Harlan(big day, start early…Harlan is about an hours drive from the Gap. 

-Start out your day at the lodge. Amazing views and a meal before you head to Chained Rock for a photo or two. Great legend attached to this spot….get it attached! 

-Court House Square, spend the afternoon shopping and eating. Our favorite spot is Sauced!

-Then take the scenic drive to Harlan

-Once in the City of Harlan, check out Sassy Trash(shopping), Moonbow(coffee) and the Portal(eats). 

-Harlan County also has ziplining and ATV trails. Plan ahead, because spaces fill up quickly. Harlan County is also home to Portal 31, an underground mine museum. 

-If you are up for another scenic trail, come back to the Gap through Virginia.


Day Five

-Today you are a bit closer to the Gap. The Abraham Lincoln Library and Museum on the Campus of Lincoln Memorial University houses the second largest collection of Lincolnia in the world. The museum recently underwent a phenomenal renovation. Ask Natalie to share with you the educational wing and a special story or two. Take a moment to explore the outdoor space, with a series of cabins and out buildings. Take a walk across campus. LMU offers a variety of programs from undergraduate through graduate studies. Go Splitters! 

-Kayaking/Tubing, while there are several options in the area, our favorites are Lazy River Kayak or Heavy’s. If Not Shelly Belle’s is also a local and offers axe throwing. 

-If not up for Powell River, then take a drive down Powell Valley and visit Speedwell Academy. Originally established in 1827, this Powell Valley Male Academy was eventually used by both sides during the Civil War. We suggest you take the old road and relax.  

-Frosty Mug is a Harrogate favorite for a burger, fries and a milkshake. Eat on site or get it to go and head to the Harrogate Park

-Woodlake for Dinner…take the drive to Tazewell (pronounced TAZWELL), a little financier than most local spots, but there is not a dress code.


Day Six

Grab a meal and be prepared for a relaxing day. 

-One of the best things to experience in the area is Wilderness Road State Park. This park features a reconstructed Martin’s Station, an outdoor living history museum. Also, at the park is the Ely House (they refer to it as Karlan), an 1870’s era home. You can also enjoy the Wilderness Road Trail(via hike, bike or horse), linking back to the Cumberland Gap National Historical Park.  Hopefully, Frances is around to tell you a family story. 

-During your time in Lee County, visit Dutch Treat for an amazing sandwich! Eat on site or take to the park for a picnic. They also have a line of specialty items available for purchase to take home. Tell Leon we sent you!

-Of course we suggest taking the backroads, old 58 is the best. Just enjoy as you explore this place. 

-Take some time this evening for a walk around town, look for the deer. Go back to a favorite spot and share a photo with us. 

Day Seven

-Grab breakfast and sit by Gap Creek one last time for this trip. 

-Take time to go back and pick up any last minute items you need from the area. 

-If you have time, stay for lunch at your favorite restaurant.


Other options while in the area: 

-Golfing, whether it’s at the Middlesboro Golf Course (the oldest continuously played course in the United States), Monte Vista, Wasioto or Woodlake, we promise you will find your fit. 

-Norris Lake…water, water everywhere. A great place to take a ride around or drop a line. 


But, don’t forget the Cumberland Gap National Historical Park website is also an excellent resource when planning a visit to the area. We have included several resources below for your convenience. 

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.