Pinnacle Overlook Trail is a 7.8 mile moderately trafficked out and back trail located near Middlesboro, Kentucky that features a waterfall and is rated as moderate. The trail offers a number of activity options and is best used from April until October. Dogs are also able to use this trail but must be kept on leash.

Distance: 7.8 miles Elevation Gain: 1,804 feet Route Type: Out & Back

dogs on leash


nature trips


bird watching






wild flowers


historic site

Note: Pinnacle Road is currently closed. However, the trails are open and visitors can walk to this trail along the road.

3 months ago

Nice walk along and over (20 water crossing the day I was there) Sugar Run creek. Cascades so many couldn't photographic all of them! There is a very LARGE rock formation about half way to Ridge Trail, looking back, after you walk about 50-60 foot past this, at the top right you will see "The Eye of the Needle".

6 months ago

This was a good challenge. A lot of uphill hiking that seemed like it wouldn’t end. But if you pace yourself, it’s doable. There is a nice overlook before you get to THE pinnacle overlook that’s perfect for privacy.

7 months ago

Nice maintained trail.

9 months ago

This trail is magical. I did it alone and didn’t pass one person. Of course the pinnacle is even busy on a Monday morning. Great workout too. Did it all in four hours with two stops at the overlooks. Didn’t see any wildlife

10 months ago

We really enjoyed this trail! The elevation gain was challenging enough without being difficult, but I would say you either need to be in shape or work in time for plenty of breaks. You cross a creek several times. A little less than a mile from the Pinnacle is an unnamed lookout that was gorgeous and not crowded like the Pinnacle. The trail is not marked but super easy to follow. We had our hiking poles and found them to be very useful. We ended up with a little over 9 miles (including walking around the Pinnacle) and just over 4.5 hours.

Sat Mar 23 2019

Participated in the 'Iron Will Hike' sponsored by the Cumberland Gap National Park, lead by trail guide David Earles. It was a great experience and a great trail. While it was a little challenging, a lot of hill climbing, there wasn't anything that required to difficult.

Mon Jan 07 2019

Pretty strenuous and I didn’t run into anyone on the trail so I would recommend to go with someone but views are awesome at the top!

Tue Jan 01 2019

My wife and I have a habit of being at Nat’l parks during government shutdowns. Last year (early 2018) on ice at the Smokies with micro spikes and now this year at the Gap. We did Iron Furnace to TriState and the up to the Overlook (via Harlan Road rail partway) without seeing more than 5 hikers. Zero cars! Our version was about 1800 feet and 5.8 miles. We also intentionally overshot the return back to iron furnace for a look at the top of Gap Creek waterfall. I recommend this combination of iron furnace to TriState over to pinnacle and back down.

Sun Dec 02 2018

Fun but be ready if you’re not used to such vertical climbs!

Mon Oct 15 2018

A must do for any Kentuckian! Historically important locale to America! Stunning scenic views and just a must!

Fri Aug 17 2018

hiked this trail from the campground. It was pretty strenuous on the way up but so beautiful with so much history!

Wed Jul 18 2018

The scenery and nature never cease to amaze me. One of my favorite views is from the pinnacle overlook.

Mon Apr 30 2018

I really enjoy this trail. I like starting at the visitors center. Starting here adds 2.2 miles on the round trip distance.

Sat Mar 24 2018

Hiked this in this snow in mid-March. It was absolutely beautiful! It’s mainly uphill going up but coming back down the mountain was a breeze.

Mon Mar 05 2018

I have hiked this trail shown on the map and THIS trail on the map is not the Pinnacle overlook trail from the Iron Furnace. This trail on the map is from an area off Hwy 988, near Sugar Run. Great hike just not accurate.

Mon Oct 23 2017

This is why I hike! Great trail, lots of uphill but nothing technically challenging. Glorious view at the top.

Thu Oct 19 2017

Great trail!

Fri Sep 08 2017

Good hike from Iron Furnace, just under two miles each way. Stay straight at tri peaks turn off then right at fork headed up, then another right where the sign says toward Pinnacle. Don't get off on any of the roads the trail crosses. 1,200 foot elevation gain so moderately challenging but nothing technically complicated. Forested almost the whole time, with expansive view at the top. 90 minutes up and back if you don't need rests.

Tue Aug 01 2017

Amazing view at the top> If this hike is too long, you can also hike from one of several parking lot strt poins along Pinacle road. (Just be careful they close the gates at sunset)

Thu Dec 01 2016

Hiked this with a group of schoolchildren- the view is worth it all!

Thu Oct 20 2016

I used to do this trail a couple of times a month when I lived in Harrogate. Its a great day hike from Iron Furnace. The last ~1 mile is the toughest part, but you get a great payoff with the view from the top.

Wed Sep 28 2016

Very beautiful overlook. I need to come back to experience it on a better day weather-wise...and so I can hike all the way up from Cumberland Gap TN below (and combine it with the Tri-State Peak Trail).

Fri Jul 01 2016

Only hiked part of this trail because we started late in the day but enjoyed it very much and plan to go back and hike the entire trail.

Tue May 10 2016

Me and my Girlfriend just walked this trail at 8.6 miles from Cumberland Gap to Pinnacle and around back to Cumberland Gap. It was a wonderful Hike and will do again. Some areas are steep but still was a great hike. We would definitely recommend this.

Tue Apr 05 2016

Be prepared to be amazed with the view.

Sun Oct 18 2015

Tuesday october 17 a perfect day to hike this trail with my husband Jeff and daughter Jennifer. The air was crisp and the sky sharp blue. The trail was not to steep but good exercise. I recommend a time when the leaves are wearing their full color...awesome. You can also drive to the overlook so once you get there it may be busy..but room for all. We ate our packed lunch from a rock to the side over looking the towns below.. Eagles were soaring! We detoured to Gap Cave on the way back down. a nice hike in all.

Fri Mar 14 2014

I loved this trail. The trail is well maintained and the views at the top as well as along the way are to die for. The one negative aspect is that the main overlook the trail ends at can also be accessed by car. The view from the rock formation before you get to the observation deck was definitely my favorite. Another awesome aspect is that the trail goes into three different states.

Sun Apr 29 2012

I believe the previous reviewer actually parked in the Pinnacle parking area at the top instead of the Sugar Run area. The trail head(s) are actually in the Sugar Run Area as noted in the guide and on the map. I hiked up from this area to the Pinnacle but walked down the road for a 10 mile total. The trail up is a nice hike and has quite a few moderately steep ascents. When you reach the Ridge trail it levels out and becomes a pleasant stroll. I will be doing this hike again but will wait for winter for better ridge top views.

21 days ago

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