Pinnacle Overlook Trail

MODERATE 25 reviews

Pinnacle Overlook Trail is a 7.8 mile out and back trail located near Middlesboro, Kentucky that features a great forest setting and is rated as moderate. The trail is primarily used for hiking, walking, trail running, and nature trips and is best used from April until October. Dogs are also able to use this trail but must be kept on leash.

7.8 miles
1804 feet
Out & Back

dogs on leash


nature trips

trail running




29 days ago

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.

1 month ago

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.

5 months ago

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

6 months ago

Great trail!

7 months ago

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.

8 months ago

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)

Thursday, December 01, 2016

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

Thursday, October 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.

Wednesday, September 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).

Friday, July 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.

Tuesday, 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.

Tuesday, April 05, 2016

Be prepared to be amazed with the view.

Sunday, October 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.

Friday, March 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.

1 month ago

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Saturday, October 29, 2016

Sunday, May 15, 2016

Saturday, November 07, 2015

Saturday, June 20, 2015

Monday, August 04, 2014

Monday, May 26, 2014