Pinnacle Overlook

Middlesboro, Kentucky 40965

Pinnacle Overlook

Pinnacle Overlook Professional Guide

Detailed Trail Description from our Guidebook

"This climb along a beautiful mountain stream to the top of Cumberland Mountain ends at a stunning overlook above Cumberland Gap.

Sugar Run is a small, picturesque stream running down the Kentucky side of Cumberland Mountain. In spring the hollow is full of wildflowers. This hike follows Sugar Run upstream and then takes Ridge Trail southwest along the mountain’s crest to the Pinnacle Overlook. From this 2,440-foot observation point, you look down on Cumberland Gap and across the mountains of three states: Kentucky, Virginia, and Tennessee."

Pinnacle Overlook Trip Reports

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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.
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don''t let the 7.8 miles scare you, it''s more like .78 miles. There are two entrances from the parking lot, one is a handicap route which is very direct and very short to the overlook. The entrance by the bathrooms is a bit longer and has more little off trails on it. The trail is completely paved all the way and is useable for everyone. It winds among the trees and hills and is very pituresque, so take your camera. You can stand in Kentucky, Virginia, and Tennesse at different times through out the trail. It''s a very easy trail.

Pinnacle Overlook Photos

Trail Information

Nearby City
Trail Type
Skill Level
5 hours
Cumberland Gap National Historical Park, (606) 248-2817
Local Contacts
Cumberland Gap National Historical Park trail maps; USGS Middlesboro North and Middlesboro South (KY/VA/TN). Park maps are free at the visitor center, which also has commercial trail maps for sale.
Local Maps

Trail Log