Nestled at the corner of Virginia, Tennessee and Kentucky is a small gap in the wall that is the Cumberland Mountains. This pass through the mountains was used for hundreds of years as a game trail and path for Indian raiding parties before becoming the Wilderness Road leading settlers into Kentucky. The area is now preserved as Cumberland Gap National Historical Park. It is a perfect spot for a weekend of history and hiking.
This 24,000-acre park has 85-miles of trails including several backcountry campgrounds, caves, historic structures and the remains of several Civil War fortifications. Atop the Pinnacles, there are views into Virginia and Tennessee for miles.
This park has far more deciduous trees than evergreens. That makes it one the best places to spend a fall weekend hiking in the eastern US. In short, we loved it and look forward to coming back.
(Disclaimer: When we link to places you can buy our stuff or places we stayed, we are using special codes which earn us commissions on the sales at no additional cost to you. Please see our Review Policy for more information.)
How to Spend a Weekend at Cumberland Gap National Historical Park
Your first stop, as with any national park, should be the Visitor Center. The Visitor Center has an excellent video on the history of the gap.
The path through the gap started as a game trail blazed by bison migrating to and from salt licks. It blows our mind that bison used to range this far east. Raiding parties from the Cherokee and Shawnee also used the gap. They raided each other’s settlements and the trail was known as the Warrior’s Path.
The park video focused on the efforts of Daniel Boone to find a path for settlers to move into Kentucky. Eventually, with a team of axemen, Boone carved out the Wilderness Road to allow wagons to cross the pass.
The exhibits in the Visitor Center trace the importance of the gap over the years. They look at it as a route through the mountains up until the construction of the tunnel through the park.
Hike up to Tri-State Peak and the Saddle of the Gap
From the Visitor Center, head into the park and stop at the Thomas Walker Parking Area. From there, hike up the Object Lesson Road to the Saddle of the Gap.
The Object Lesson Road is a leftover from a US Department of Agriculture program. The government promoted using light gravel instead of dirt roads to help control erosion and dust. It’s an easy uphill to the Saddle of the Gap. This spot, marked by a sign, is the highest point of the pass. You will find a sign marking the significance.
This spot is the crux of this park but it is not that picturesque. Still, it is cool to know you are standing where Daniel Boone led settlers through the mountains and into Kentucky. Indeed, just down the trail toward the Tri-State Peak is a large monument to Boone.
A little further down the trail, you will find a small crater and a spur trail leading off to one of the many “forts” in the park.
The crater is leftover from the Civil War. Union troops blew a supply of ammunition as they retreated from Cumberland Gap, preventing it from falling into Confederate hands.
Tri-State Peak allows you stand on the spot where Tennessee, Kentucky and Virginia meet. There is a nice pavilion and a decent view toward Middlesboro, KY below.
As we headed back, we detoured along the Wilderness Road Trail, which follows the original route of the path leading through the woods.
All told, we spent about 90 minutes on the trail and covered 3.5 miles with a 733-foot elevation gain. While there were a few spots we felt the uphill, this was a relatively easy hike. If you are going to do no other hiking in the park, this is a good choice.
Drive the Pinnacle Road
The most scenic area of the park sits atop the ridge straddling between Kentucky and Virginia. In order to get up there, you have two options: hike or drive. For most folks, driving is going to be the preferred option.
From the Thomas Walker Parking Area, take the winding Pinnacle Road up the mountain towards the top. Just bear two things in mind: you cannot take any vehicle more than 20 feet long up the road and there is limited parking at the top.
Along the way up, you will find a small turn off for Fort McCook. Stop here to check out the earthen Civil War fortification. It’s really more of a redoubt than a fort. It is still worth the stop to learn how the Civil War impacted this area.
As you keep following the road up to the top, there is a nice pull off on the left which gives an excellent view into Kentucky. There’s not a ton of room so you may want to hit it on the way back down.
Once at the top, you might be tempted to head straight for the Pinnacle Overlook. If you have time, we recommend checking out the Powell Valley Overlook and Fort Lyon, another Civil War fortification, first. This saves the best view for last.
Pinnacle Overlook is spectacular, especially at sunset. It is well worth your time to head up here at sunset to check out the view.
Hiking the Sugar Run Trail
If you are looking to see the Pinnacle Overlook but want more of a challenge, hiking-wise, the Sugar Run Trail combined with a section of the Ridge Trail, the Fort McCook Trail and the Harlan Road Trail forms a nearly 9-mile loop with a 1,800-foot elevation gain.
There are two places you can pick up this trail: the trailhead or the Sugar Run Picnic Area. We parked at the picnic area and followed the trail along the Sugar Run Creek up to Ridge Trail, then cut back towards the Pinnacle Overlook then down to Fort McCook.
Once you get past Fort McCook, you have to cross the road and briefly walk along the road before picking up the Harlan Road Trail back to the parking area. The Harlan Road Trail follows the old Harland Road bed, which was constructed to get cannons up to the Fort McCook and Fort Lyon during the Civil War.
We really enjoyed this loop. The ranger who recommended the trail to us said to keep an out for mushrooms and the trail did not disappoint. We saw plenty of really cool mushrooms along the way.
All that said, the trail did kick our butts when combined with the Tri-State Peak hike. If we had it to do over again, we might have skipped this hike to be able to another hike out on the east end of the park out to Sand Cave and White Rocks Overlook.
But after doing about 12 miles in one day, we weren’t feeling another 10-miles and 2,000 feet of elevation gain. Since you can see pretty much everything on this hike by driving up the Pinnacle Road, it is not necessary to enjoy the park.
Iron Furnace and Wilderness Road Campground
On the Tennessee/Virginia side of the park, you will find the small town of Cumberland Gap, which has great views of the gap itself. If you stop at the Daniel Boone Visitor Information Center, you can hike the Wilderness Road up to the Saddle of the Gap from that side of the mountains. If you are looking to follow in Boone’s footsteps, this is a great spot to do so.
You will also find the Iron Furnace on this side of the mountain. The Iron Furnace dates back to 1819. Locally mined iron along with limestone would be used to create pig iron ingots, some of which would be used by local blacksmiths but most of which would be shipped to down the Powell River to Chattanooga.
Not far down the road is the Wilderness Road Campground, which is a nice campground with some electric sites and is home to a nice nature loop trail. It’s only a mile but it is quite pretty. If you are staying at the campground, it’s worth your time.
Two of the major attractions of the park, Gap Cave and the Hensley Settlement, were closed when we visited due to COVID-19.
The Gap Cave is a cave system that is only accessible via a ranger-led tour. The cave is home to bats and salamanders and some pretty cool cave formations, at least according to pictures.
The Hensley Settlement was open but the only way to get to it during COVID-19 was to hike a 10-mile one way trail. Normally, you can take a ranger-led tour which involves being shuttled to the area in a van as the road there is only open to park service vehicles.
Honestly, the Hensley Settlement is the one thing I think our visit to a national historical park really needed: historic buildings, though we did get some of that by visiting the nearby Wilderness Road State Park (see below).
Obviously, we need to come back to see these highlights once the COVID-19 pandemic passes. We also feel like coming back on a fall weekend would be a great time to see the changing leaves.
Wilderness Road State Park
This state park is right down the road from Cumberland Gap National Historical Park and is really everything that is missing from the national historical park in terms of telling the story of the gap.
This excellent state park tells the story of Martin’s Station, the frontier fort and trading post that served as the westernmost outpost before heading to Kentucky through the gap.
The fort had several reenactors dressed in period attire to explain the various parts of the fort, including how the cabins within the fort worked as fortifications against Indian attacks. The fort has a working smithy and one of the reenactors demonstrated how period blacksmiths would have worked. There was also a gunsmith demonstrating how rifles were built and which long guns were popular during the time.
Lastly, the park has a small bison pasture. Now, these bison aren’t the subspecies that was found in the eastern US all that time ago but, still, it is really cool to see their cousins make a return to this part of the world.
We highly recommend visiting Wilderness Road State Park on your visit to Cumberland Gap National Historical Park. The two parks really are two sides of the same coin.
Where to Stay and Eat Near Cumberland Gap National Historical Park
The surrounding towns around Cumberland Gap National Historical Park are relatively small and there is not a lot in the way of hotels or campgrounds.
In terms of camping, if you don’t have a large camper or are tent camping and don’t mind being without full hookups, the Wilderness Road Campground was quite nice when we drove through.
In terms of hotels, we stayed at the Holiday Inn Express in Middlesboro, KY, which is right down the road from the Visitor Center. We found the hotel quite comfortable and the folks working there were great. Our only minor complaint was our room being located next to the elevator, which was a bit noisy. We will certainly stay here again when we return.
We got dinner after hiking at Pelancho’s, a pretty good Mexican restaurant right down the road from our hotel. We split an order of fajitas and got some pretty tasty margaritas to help recover from doing more than 10 miles on the trail. It was quite good.
We also got lunch over in Harrogate, TN at the Haymaker Farms Restaurant. We got a couple of BBQ sandwiches, which really hit the spot. I had the Korean-style BBQ and Bonnie had the Haymaker special, which we both enjoyed.
Final Thoughts on Cumberland Gap National Historical Park
This park is perfect for a weekend getaway, especially if you want to get out on the trail. You cannot overstate the part this place played in early westward expansion.
While you could visit this park in a day and see most everything, an extra day would make all the difference in being able to get in tours (once they are available again) or a solid hike.
Be sure you check out the Wilderness Road State Park right down the road in Virginia. It is well worth your time and it really is the missing piece for the historical picture at Cumberland Gap National Historical Park.
We use Skyscanner to find deals on flights. Skyscanner has a great interface and compares tons of airlines for the best pricing and routing. That said, it does not always have every airline and some airlines will have better deals on their website. Still, Skyscanner is a great place to start.
Click here to search for a flight.
We typically stay at Hilton properties, so we use the Hilton website. We can find good Hilton Honors discounts or AAA discounts for a hotel there. We make great use of our free night certificates from our Hilton Honors American Express.
If there are no Hilton properties available, we use TripAdvisor to read reviews and book the hotel. We find we can get the best price that way.
Click here to search for a hotel.
We use Vrbo for the times when we have rented a cabin for a weekend getaway, like this cabin in Townsend, TN, or needed to rent a house for a large family vacation. We had a great experience with them in terms of refunding deposits when COVID hit and will continue to use them.
Click here to search for a vacation rental.
As a general rule, we book with Hertz for rental cars. We have had nothing but good experiences with them. Plus, we really like unlimited mileage and not worrying about crossing state lines. We have even rented from Hertz overseas in both Slovenia and Croatia.
Click here to book a rental car.
We have found some amazing prices booking a cruise through Cruise Direct. We have saved a lot of money on our cruises compared to what we found elsewhere, making a last-minute Bahamas cruise even cheaper.
Click here to book a cruise.
We highly recommend Outdoorsy for RV rentals. We rented a camper van for a week to visit Rocky Mountain National Park for the elk rut and Custer State Park for the Buffalo Round-Up and had a blast. The program was easy to use and we really enjoyed the freedom of having a camper van for that trip.
Click here to rent an RV.
We don’t often book tours. Typically, we like to do stuff on our own. That said, there are some experiences you just can’t have any other way. So, when we do want to book a tour, we always check Viatour first.
Click here to book a tour.
We make extensive use of both Good Sam and AAA on the road. Good Sam is normally regarded as a discount card for RVers at campgrounds and Camping World but anyone can use the 5 cents off a gallon at the pump at both Pilot and Flying J.
Click here to get a Good Sam membership.
We have had AAA as long as we have been married and it has more than paid for itself in discounts at hotels, aside from the peace of mind of having roadside assistance. Add in paper maps and the ability to get an international driver’s license and it is more than worth it for any traveler out there.