How many trails are near Middlesboro?

We list 108 trails within 30 miles of Middlesboro, Kentucky. This page shows the 60 closest.

What is the longest trail near Middlesboro?

Ridge Trail is the longest on this page at about 15 miles, 6.6 miles from Middlesboro.

Are there dog-friendly trails near Middlesboro?

None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.

Trails near Middlesboro, KY

108 trails within 30 miles of Middlesboro, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (96) Walking trails (94) Bike trails (20) Mountain bike trails (17) Paved trails (11) Horse trails (24) ATV and UTV trails (10) Off-road and 4x4 trails (14) Dog-friendly trails (4) Greenways (6)

Quick picks

Closest: Bicycle Trail 0.8 mi, 0.8 mi away
Longest: Ridge Trail 15 mi, 6.6 mi away
Easy walk: Fitness Trail 1.4 mi, 1.4 mi away
Paved: Cumberland Gap Greenway 1.7 mi, 3.3 mi away
Mountain biking: Wilderness Road Trail 8.7 mi, 6.8 mi away
Horseback riding: Sugar Run Trail 2.1 mi, 3.8 mi away

All nearby trails

Bicycle Trail

0.8 mi away

0.8 mi long · Easy · Cumberland Gap National Historical Park

Hiking Biking Paved

Fitness Trail

1.4 mi away

1.4 mi long · Cumberland Gap National Historical Park

Hiking

Thomas Walker Trail

2.1 mi away

0.9 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Object Lesson Road

2.1 mi away

0.3 mi long · Cumberland Gap National Historical Park

Hiking

Fort Foote Trail

2.2 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking

Tri State Trail

2.3 mi away

0.6 mi long · Cumberland Gap National Historical Park

Hiking

Cumberland Trail

2.4 mi away

2.5 mi long · Cumberland Gap National Historical Park

Hiking

Ft. McCook Spur Trail

2.4 mi away

0.0 mi long · Cumberland Gap National Historical Park

Hiking

Harlan Road Trail

2.4 mi away

2.0 mi long · Cumberland Gap National Historical Park

Hiking

Tri-State Peak Trail

2.4 mi away

0.6 mi long · Harrogate

Hiking

Iron Furance Path

2.7 mi away

0.1 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Tennessee Road Trail

2.7 mi away

0.3 mi long · Cumberland Gap National Historical Park

Hiking

Whitt's Ridge Trail

2.7 mi away

1.1 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Pinnacle Overlook Trail

2.7 mi away

0.2 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Ft. McCook Trail

2.7 mi away

0.7 mi long · Cumberland Gap National Historical Park

Hiking

Fort Lyon Trail

2.8 mi away

0.2 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Gap Cave Exit

2.8 mi away

0.1 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Pinnacle Trail

2.8 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking

Gap Cave Entrance

2.9 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking

LMU Trail

3.0 mi away

1.4 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Cumberland Gap Boardwalk

3.1 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking

Gap Overlook Trail

3.2 mi away

0.4 mi long · Cumberland Gap National Historical Park

Hiking

Wilderness Road Trail

3.2 mi away

1.9 mi long · Cumberland Gap National Historical Park

Hiking

Daniel Boone Parking Area Spur

3.2 mi away

0.0 mi long · Easy · Cumberland Gap National Historical Park

Hiking Biking Paved

Jenny's Lane Trail

3.2 mi away

0.3 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Gap Overlook Loop Trail

3.2 mi away

0.2 mi long · Cumberland Gap National Historical Park

Hiking

Sugar Run Picnic Trail

3.2 mi away

0.9 mi long · Cumberland Gap National Historical Park

Hiking

Little Pinnacle Trail

3.3 mi away

0.2 mi long · Cumberland Gap National Historical Park

Hiking

Cumberland Gap Greenway

3.3 mi away

1.7 mi long · Easy · Cumberland Gap National Historical Park

Paved Greenway

Little Tunnel

3.3 mi away

0.3 mi long · Easy · Cumberland Gap National Historical Park

Hiking Biking Paved

Jones Farm Road

3.7 mi away

0.7 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Penny Lane Trail

3.7 mi away

1.1 mi long · Cumberland Gap National Historical Park

Sugar Run Trail

3.8 mi away

2.1 mi long · Cumberland Gap National Historical Park

Hiking Horses

Skylight Cave Trail

4.1 mi away

0.0 mi long · Cumberland Gap National Historical Park

Hiking

Lewis Hollow Connector Trail

4.2 mi away

0.2 mi long · Cumberland Gap National Historical Park

Hiking

Boone Trail

4.4 mi away

1.5 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking

Colson Trail

4.5 mi away

0.8 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking Horses

Greenleaf Trail Connector

4.6 mi away

0.0 mi long · Cumberland Gap National Historical Park

Hiking

Honey Tree Trail Connector

4.6 mi away

0.0 mi long · Cumberland Gap National Historical Park

Hiking

Service Road

4.6 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking

Honey Tree Spur Trail

4.6 mi away

1.0 mi long · Cumberland Gap National Historical Park

Hiking

Lewis Hollow Trail

4.7 mi away

1.6 mi long · Cumberland Gap National Historical Park

Hiking

Campground Path

4.7 mi away

0.3 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Colson Lane

4.7 mi away

0.5 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking Horses

Greenleaf Nature Trail

4.7 mi away

0.6 mi long · Cumberland Gap National Historical Park

Hiking

Ampitheater Walkway

4.8 mi away

0.0 mi long · Easy · Cumberland Gap National Historical Park

Hiking Paved

Gibson Gap Trail Connector

4.8 mi away

0.0 mi long · Cumberland Gap National Historical Park

Hiking

Wilderness Road Rails to Trails

5.0 mi away

8.4 mi long · Cumberland Gap National Historical Park

Ridge Trail

6.6 mi away

15 mi long · Cumberland Gap National Historical Park

Hiking Horses

Gibson Gap Trail

6.6 mi away

4.4 mi long · Cumberland Gap National Historical Park

Hiking Horses

Gibson Gap Camp Water Trail

6.7 mi away

0.1 mi long · Cumberland Gap National Historical Park

Hiking Horses

Wilderness Road Trail

6.8 mi away

8.7 mi long · Virginia Department of Conservation and Recreation

Hiking Biking Mountain biking Horses

Davisburg Trail

7.7 mi away

4.5 mi long · Middlesboro

Davis Bird Trail

7.7 mi away

0.7 mi long · Middlesboro

Clear Creek Fitness Trail

8.4 mi away

0.9 mi long · Pineville

Hiking

Chenoa Trail

8.4 mi away

4.7 mi long · Middlesboro

Shillalah Creek Trail

8.5 mi away

4.8 mi long · Cumberland Gap National Historical Park

Hiking Biking Mountain biking Horses

Laurel Cove Trail

9.4 mi away

1.2 mi long · Moderate · Pineville

Hiking

Indian Ridge Trail

11 mi away

0.8 mi long · Virginia Department of Conservation and Recreation

Hiking

Pioneer Loop

11 mi away

0.7 mi long · Easy · Virginia Department of Conservation and Recreation

Hiking Biking Mountain biking

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Nearby cities

All trails in Kentucky

Common questions

How many trails are near Middlesboro?: We list 108 trails within 30 miles of Middlesboro, Kentucky. This page shows the 60 closest.
What is the longest trail near Middlesboro?: Ridge Trail is the longest on this page at about 15 miles, 6.6 miles from Middlesboro.
Are there dog-friendly trails near Middlesboro?: None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.