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Visit Cumberland Gap For A Day of Family Fun

Every year at the start of school, T and I fill out our goals sheet. On that form, we fill in what we hope to discover, improve, and accomplish in the coming year. This year, Cumberland Gap National Historical Park in Middlesboro Kentucky was my pick for a place I wanted to visit that I have never seen before. So, when it came time to plan our last field trip of the year I was quick to suggest it.

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For the record, we couldn’t do a final field trip to T’s destination pick because he chose Baton, Rouge, Louisiana. That’s hard to manage in a day trip. But, despite the lack of Cajun flavors, we ended up having a memorable final day of eleventh grade that we both will remember fondly. Also, we ate foot-long fried hotdogs at Conley’s Diner, and while not gumbo, they were still very satisfying. It was an amazing day. Let me tell you all about it.

Pinnacle Overlook (elevation 2,440 feet) in Cumberland Gap National Historic Park where you have a spectacular view into Kentucky, Virginia, and Tennessee

What Will You Find In Cumberland Gap?

  • Amazing views like Pinnacle Overlook (elevation 2,440 feet) where you have a spectacular view into Kentucky, Virginia, and Tennessee.
  • 85 miles of trails
  • Gap Cave – Estimated to be 3-5 million years old—and still forming.
    • Call ahead and secure your spot to join park rangers on a two-hour exploration of Gap Cave, a majestic underground cathedral where nature’s story is etched in rock and sand. See glistening stalagmites and flowstone cascades, as well as marks made by Civil War soldiers on this 1.5-mile tour spanning four levels of the cave.NationalParks.org
  • Groves of hemlock – (Sugar Run Trail)
  • Fields of wildflowers (Find a great trails list from alltrails right here)
  • Meadows of rhododendron and fiddle ferns. 
  • Waterfalls
  • Historical Landmarks – During the Civil War both the North and South held the Gap.
  • Hensley Settlement
    • Join park rangers and step into the past at the historic Hensley Settlement on top of Brush Mountain. Stroll down fence-lined lanes, step into the blacksmith’s shop, look into the springhouse and sit in the one-room schoolhouse. The Hensley Settlement was established in 1903 by Sherman Hensley and was occupied until 1951. The historic buildings remain and can be visited on this 3 1/2 to 4-hour tour.National Park Service
  • Wildlife – the current recorded number of animal species is 371.
  • Visitors Center Museum
Cumberland Gap sign

Why Is Cumberland Gap important?

Cumberland Gap Trails

Cumberland Gap National Park has a lot to offer including a rich history. Hundreds of millions of years ago in Middlesboro, KY which can be viewed from The Pinnacle Overlook in Cumberland Gap National Historic Park, is the site where a 4-mile wide asteroid landed creating a geological landscape that scientists adore for all it tells of the past.

There was also a time when the Shawnee and Cherokee used the Warrior’s Path through the gap as a game trail because buffalo and deer lived there in abundance.

Then it lent passage to overland emigrants in the early phase of the westward movement. Abraham Lincoln’s parents and grandparents traveled Wilderness Road through Cumberland Gap as they emigrated west. 

It also played a role in the Civil War being occupied by both the North and the South. We visited a cannon located at historic Fort Lyon near the Pinnacle Overlook.


Today, Cumberland Gap is home to spectacular scenery, vast vistas, unique geologic sandstone formations, underground caverns, and diverse plant and animal life.


Can You Drive Through Cumberland Gap

Cumberland Gap offers many trails that cross streams. There are plenty of bridges to keep your feet dry.
Trails cross the water frequently but sturdy bridges will keep your feet dry.

T and I drove from the visitors center up the mountain, a four-mile road to the Pinnacle, making three stops at trailheads along the way. It is a beautiful drive and we hardly encountered any traffic in late May.

How Do You Get To Cumberland Gap

Cumberland Gap Water

Cumberland Gap National Historic Park Address and Details:

91 Bartlett Park Road, Middlesboro, KY 40965

Phone Number: (606) 248-2817

Cumberland Gap Website: https://www.nps.gov/cuga/index.htm

Admission Costs: No entry fees. Guided Cave Tours run from $8 and Hensley Settlement Tours $10. Discounts are offered to seniors and children ages 5 – 12.

Song About Cumberland Gap

For more resources about the Cumberland Gap check out these posts:

This was the perfect educational field trip to finish off our school year and we genuinely enjoyed every second of it. To get the most out of your time there sign up for the tours. You can learn so much and rangers really bring the past alive.

Have you visited this park before? If so, share your thoughts in the comments section below. We love to hear from you.

Other Family-Friendly Nature Destinations We Recommend

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