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First Time Visit to Cumberland Gap National Historical Park

If you are looking forward to hiking in the woods, viewing grand vistas and walking in the footsteps of our pioneering ancestors, then take a first time visit to Cumberland Gap National Historical Park.

Entering this area, you get the aura of Daniel Boone and Davy Crockett. While Daniel Boone did play a much larger role in establishing the Wilderness Trail, Crockett did work in at a haberdashery along the trail in 1799.

With this bit of knowledge, I began humming the old Ballad of Davy Crockett song from the 1950’s Disney TV show. My kids thought I was nuts, which is pretty much par for the course. 

You certainly don’t have to don a raccoon hat or whistle an old TV theme song to enjoy your time here (I think it helps though.) Let’s dive into what you can find on a visit back to the American Frontier.

Table of Contents

Park Map

Spanning across three states, Virginia, Tennesse and Kentucky, the Cumberland Gap NHP spans 24,000 acres over the Cumberland mountains.

map of Cumberland Gap NHS

Facts about Cumberland Gap National Historical Site

  • The Cumberland Gap NHP has over 85 miles of hiking trails.
  • The park boundary spans over 24,000 acres of land across three states, Virginia, Tennessee and Kentucky.
  • The park is a Fee-Free Park, so an entrance fee is not required.
  • Gap Cave (aka Cudjos Cave) is within the park and has a length of 18.5m, making it the 42nd largest cave in the United States.

Things to Do at Cumberland Gap National Historical Park

  • Hike to the Historic Cumberland Gap: Walk where pioneers, American Indians and Civil War soldiers walked.
  • Take a guided tour of Gap Cave: Traverse 183 steps and investigate some amazing rock structures. There is a fee and offered only May-Oct.
  • Get a National Park Passport Stamp at the Visitor Center.
  • Tour Hensley Settlement: Visit a turn of the century settlement. Tours leave the visitor center via shuttle and there is a fee.
  • Visit Pinnacle Peak: An awesome view and a fun drive or hike to the peak!
External view before entering Cumberland Gap Tunnel
Cumberland Gap Tunnel

Depending on the direction you are coming from, you may need to drive through the Cumberland gap tunnel to get to the visitor center. To access certain parts of the park you may have to go through the tunnel, heading away from the visitor center. 

External Sign for the Cumberland Gap National Historical Park

Man watching Cooper Interpreter at working on a barrel Cumberland gap visitor center

Address: 1 Skyland Road, Middlesboro, KY 40965

The Visitor Center itself was very welcoming with a large two-story high foyer which included the information desk, bookstore and a staircase to the next level. 

During our visited we were presented with an interpreter who was demonstrating coopering skills (barrel and bucket making) in the area right in front of the entrance.  Very interesting.

As usual the Park Rangers were very nice and kindly provided information on the short hike to the crossroads of the original Cumberland gap, and the route to get to Pinnacle Peak

Lobby of the Cumberland Gap Historical Park
Lobby of Cumberland Gap National Historic Park Visitor Center

History and beauty at the Cumberland Gap

There are displays and exhibits on the same level of the bookstore that walk you through the various historical stages of the Cumberland gap.

This takes you back to the formation of the rock and streams, through the use by Native Americans, early pioneers, fortifications during the Civil War and life in an early mountain community. 

Cumberland Gap Visitors Center Exhibit

Don’t forget to go upstairs to see the video overview of the park. Bonus is you can watch while rocking in some old timey rocking chairs! I had the pleasure of having my chair getting consistently kicked throughout the presentation by my son.

Along with the interpreter outside, they also had someone upstairs educating visitors on how clothing was made on the frontier in the late 1700’s to early 1800’s.  

My daughter and I spent some time learning about the level of effort, care, skill and the immense amount of time needed to sustain a family who lived in these southern mountains.

A Stamping Tragedy at Cumberland Gap

When I was talking with the park rangers, I ask about the National Park Cancellation stamps and they were quick to remark, “Well you can use the ones that weren’t stolen.”  (!) Yes, Stolen. Unfortunately, three stamps were stolen by a visitor recently. 

Luckily, the primary stamp for the location was still available. Make sure to collect your stamp on your visit!

Stamp of Cumberland National Historic Park Pinnacle peak

National Park passport cancellation stamps are a great, no cost, low impact way to commemorate a visit to one of our National Parks. We have an entire article dedicated to explaining the program and how to get the most out of it.

  • Distance: 1.1m
  • Elevation gain: 226ft
  • Route Type: Out and Back
  • Difficulty: Easy

To hike this trail, you need to drive a short way to the Thomas Walker parking area. You will find the trail head for Object Lesson Road at the end of the parking lot, which leads to the Cumberland Gap, Tri-State Peak and the Thomas Walker trail was found on the right side of the parking lot. See if you can find the cool carving on the post next to the trail head.

Remember to use your Leave No Trace (NLT) principals when hiking the trails!

Trail head sign for Object Lesson Road
Trail head sign for Object Lesson Road to the Cumberland Gap.

What is ‘object lesson road’?

The object lesson road follows an old roadbed that was used in 1907 to illustrate best practices of road design. Apparently, many roads of the era were no better than what Daniel Boone traversed (Wilderness Road) over a hundred years prior. 

The ‘modern’ gravel road provided better visibility and had grading that made it more traversable and with good drainage. This object lesson was to convince the locals to support the building of these new roads.

Inset Map showing detail of Object Lesson Info Sign in Cumberland Gap National Historic Park
Inset Map Detail of Object Lesson Road

Indian Rock

We eventually found them at the trail head intersection for the longer and steeper Wilderness Road, which was the original ‘Daniel Boone’ style road. Near this intersection we also found ‘Indian rock’. 

Detail of plaque on Indian Rock in the Cumberland Gap National Historic Park
Plaque on Indian Rock

Saddle of the Cumberland Gap

We continued on the object lesson road, and eventually came to the saddle of the famed Cumberland Gap. While it had a sign that just said, ‘This is the Cumberland Gap”, I appreciate that they also put a poetic framing of the site as well:

“Salt seeking buffalo, Moccasin clad warriors, Dreaming Pioneers, Battling Civil War Soldiers. Each was here in the Historic Cumberland Gap and now so are you.”

Sign that reads 'This is the Historic Cumberland Gap'
This is the Historic Cumberland Gap
Trail sign in Cumberland Gap National Historic Park for Harlan Road, Fort McCook and Pinnacle Overlook
Trail head on Object Lesson Road

This trail intersects with the trail that heads further up to Pinnacle Peak. We decided to walk back down and then drive up to the peak. If you have time, you can absolutely hike up to the peak for an extra challenge.

green topographical trail map of cumberland gap and pinnacle peak
Wilderness trail to Cumberland Gap highlighted

NOTE: If you want to learn more about the Cumberland Gap and its history, the NPS has a great pamphlet on their site from the Tennessee historical society @1964 that you can check out.

The last bit of driving took us up Pinnacle Road to the Pinnacle peak overlook. Check the map above to see the twisty road you will need to navigate to get to the top.

Apparently, this road, with the very steep grade and numerous switchbacks, was a big hit when it opened 1929. They actually charged an admission for the joy of driving up the road!

GPS map for drive off pinacle peak in Cumberland national historic park
GPS Driving map to Pinnacle Peak

There is two ways from the parking lot to get to the peak. There is a steep incline path that is the most direct route. This path also brings you next to Earth Work remains of the Civil War era Fort Pitt and Fort Nathaniel Lewis.

There is also a more accessible route on the other side of the parking lot that reduces the strain on the legs.

The view from the overlook is magnificent and you can absolutely understand the desire to take in such an amazing view. Just down the path from the main overlook is the unique Tri-state overlook.

View of valley with green mountains and river under a cloudy sky
Tri-State Overlook

A sign indicates the mountain where all three states meet, Virginia, Tennessee, and Kentucky. Walking along the path you actually cross the state line from Tennessee and Virginia!

There is a path to a larger observation area where we can get a broad view of the mountain range and enjoy the breathtaking views.

Girl looking out at a wide-angle view from Pinnacle Peak Overlook on our first time visit to Cumberland Gap National Historic Park
Pinnacle Peak Overlook

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