Looking for the best trails around Middlesboro?

Explore the best rated trails in Middlesboro, KY, whether you're looking for an easy walking trail or a bike trail like the James White Greenway and Middlebrook Greenway . With more than 20 trails covering 77 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Holston River Greenway (Holston River Park)

We love walking this trail. You have the quiet walk in the woods. Wide paths. We walk through thr woods and then walk by the water and around the outside loop. One of our go to places to walk.

March, 2025 by jenhopkins2400

We love walking this trail. You have the quiet walk in the woods. Wide paths. We walk through thr woods and then walk by the water and around the outside loop. One of our go to places to walk.

Melton Lake Greenway

Work Off Winter Fluff

March, 2025 by mlawlor72

This is a great trail for working off your winter fluff - it is challenging in areas with hills which for those of us who spent the winter either shoveling snow or hibernating (me) came as a surprise! The trail itself is paved with asphalt or concrete slabs. The asphalt areas have tree roots humps and bumps accompanied with a couple heaves. The poured concrete slabs were in decent shape. The trail goes alongside Melton Lake - pretty early spring views from the bluff. Many people were out enjoying the warm temps and the crew teams were out on the water. I

Wilderness Road Trail

great ride. very enjoyable

August, 2024 by ksalyer10

Got to see the buffalo (plus). Nice shady ride Parked at visitor center and rode both ways and back. Rode 14 miles total.

Accordion

Wilderness Road Trail

One of our favorites

June, 2024 by c6nnhdk4bd

We road this trail with some friends today. Ages ranged from 47-71. It was a nice, cool, refreshing bike ride. Nice and straight with no hills. Favorite part was the old fort and the history we learned while there. One thing is that the map on this app is wrong as to where it begins and ends. We actually parked at the visitor center to the fort and road the trail because where the map shows it was not correct.

Knoxville City Greenways

River view

April, 2024 by shelbejo23

My son and I completed 5/30 miles of the Knoxville greenway. It was beautiful! The nature and animals we saw during the ride was incredible! We at lunch and Calhouns on the River and the picked back up for the rest of our ride.

Wilderness Road Trail

Very nice trail!

September, 2023 by mandy.smith2020

This is one of the best trails we have ever went on. It is a beautiful, flat, easy, shaded trail. SO much history. Stop at the park and check out the fort, they have people in there dressed up and making things. Very neat to see! There are picnic tables along the trail if you want to pack a lunch. There is also a buffalo viewing area. I can’t say enough good things about this trail. My group loved it!

Wilderness Road Trail

Easy Trail

June, 2023 by hippykamp

If you are in the area then load up the bikes and ride it. Pretty much flat trail that is for the most part shaded. Park at either end and ride out and back. Don’t forget to stop and see the visitor center and the homestead recreation and especially the buffalo

Knoxville City Greenways

We did the parts along the river downtown very Scenic. We uploaded photos here and at a trails facebook group https://facebook.com/groups/railstotrailsbiketrips/

June, 2023 by njriverman_tl

We did the parts along the river downtown very Scenic. We uploaded photos here and at a trails facebook group https://facebook.com/groups/railstotrailsbiketrips/

Third Creek Greenway

Short trail but fun to ride.

April, 2023 by sportyprof

Short trail but fun to ride.

Neyland Greenway

Nice trail along streams and the river. You do cross traffic a few times.

April, 2023 by sportyprof

Nice trail along streams and the river. You do cross traffic a few times.

Bearden Village Greenway

A few small curves and hilly areas. Pleasant ride with benches on the path

April, 2023 by sportyprof

A few small curves and hilly areas. Pleasant ride with benches on the path

Bearden Village Greenway

A few small ups and downs. Partially shaded And pleasant

April, 2023 by sportyprof

A few small ups and downs. Partially shaded And pleasant

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