Beginner Off-Road Trails Near Winchester, Kentucky

Henry Mtn Rd

This is a beautiful gravel road that leads to a walking trail for the old cottage furnace. It is easy gravel road with beautiful trees and wildlife. There are a few other side roads that…
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Total Miles
4.2
Tech Rating
1 Easy
Best Time
Sp / Su / Fa / Wi

Fitchburg Stone Furnace

The Fitchburg Furnace is a historic iron furnace located in the Daniel Boone National Forest in Estill County, KY. The furnace is the world's largest charcoal iron furnace and the last to be built in…
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Total Miles
3.3
Tech Rating
1 Easy
Best Time
Sp / Su / Fa / Wi

Indian Creek Road

Indian Creek Road located in one of the northern portions of Daniel Boone National Forest and is a popular local summer destination for camping, swimming, and fishing. The majority of the road is gravel, two…
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Total Miles
4.5
Tech Rating
1 Easy
Best Time
Sp / Su

Wentworth School Rd

The trail less traveled. This is an old road that leads to the Smyth Cemetery. Its a nice easy trail with a lot of low hanging branches.
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Total Miles
2.5
Tech Rating
1 Easy
Best Time
Sp / Su / Fa / Wi

Fixer Rd DBBB

Fixer Road is another section of the Daniel Boone Backwood Byway. This trail has a creek crossing, a creek bed section and some mud. It is very scenic and ties in with a few other…
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Total Miles
2
Tech Rating
3 Easy
Best Time
Sp / Su / Fa / Wi

Bald Rock Fork Rd

This is a great trail for beginners, and has a little bit of everything. Mostly gravel roads with a couple creek crossings, creek bed and a steep gravel hill. There are old oil buildings and…
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Total Miles
2.2
Tech Rating
3 Easy
Best Time
Sp / Su / Fa / Wi

Cave Fork Rd DBBB

A beautiful trail with plenty of scenery and a few shallow creek crossings. There are plenty of spots to pull over and enjoy the outdoors, and the creeks are cold and clear. This trail is…
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