Beginner Off-Road Trails Near Winchester, Kentucky

A scenic gravel lane travels through part of the Eastern Kentucky University campus. This trail goes through farmland to reach the Taylor Fork Ecological Area. Along the way, you will see wildlife, remnants of old…
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This county road is an unmaintained route that connects the community of Baldwin to Newby. It has one small creek crossing and has a rock and gravel surface. Taking this route will easily connect you…
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From the mouth of Jackson Branch at Silver Creek, you will ascend a narrow rock trail to the power line clearing and travel down Woodland Heights Road, or you can travel in the opposite direction…
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This is a part of the unmaintained county road, Maple Grove Road. This trail travels along Silver Creek and has many offshoots and playground areas. Large mud holes, hill climbs, the wall, and other fun…
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This trail runs between Newby and Bogie Mill. It is known locally as Eddington Lane or Newby Road. This trail will take you right into Silver Creek, with beautiful farmland and a covered bridge nearby…
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This is a beautiful gravel road that leads to a walking trail for the old cottage furnace. It is an easy gravel road with beautiful trees and wildlife. There are a few other side roads…
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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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Billey Fork road is on the west side of the park and runs with Red's Hollow and is between trails 15 and 16. This is a maintained gravel road and will have other trails that…
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Trail 15 is a fairly new trail that is maintained gravel and dirt road. This trail goes into the park at Billey Fork and wraps into the park and comes back down to a dead-end…
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Trail 16 is a fairly new trail that is maintained gravel and dirt road. This trail goes into the park at Trail 29 and 31, and wraps into the park and comes back down. This…
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Trail 29 is a short gravel road trail that will allow the connection of Trail 15, 31, and Billey Fork Road. Additionally, Red Hollow Road is off of this trail as well, which will lead…
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Trail 11 is a lengthy trail that runs through the west side of the park that has many trails coming off of it. This could be considered one of the main thoroughfares through this side…
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Trail 12 is a lengthy trail that runs through the west side of the park, which has many trails coming off of it. This could be considered one of the main thoroughfares through this side…
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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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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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Trail 8 is somewhat of a connector from the east side of the park to the west side of the park. This is an overall easy trail that allows easy passing of vehicles and is…
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Trail 10 is a short two-part trail that will connect the west side of the park with several trails. This will be more of a bypass trail from Barkers Branch Road that will lead down…
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Green Pond Ridge Road is part of the Daniel Boone Backcountry Byway and is a well-maintained gravel road with no obstacles. Traveling this road should give you no problems in any 4WD vehicle. Highly unlikely…
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Trail 5A is an easy connector trail for trails 3, 4, 7, 8, and 46. You will find plenty of room to pass other vehicles. This is an easy-maintained trail that will lead to other…
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Trail 3 is an overall easy trail that runs between Trails 4 and 5. This trail is a quick run to the northeast side of the park to access several more difficult trails. Enjoy this…
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Trail 7 is a nice and easy scenic trail that starts out at Trail 5A and crosses over Trail 3. It travels along a ridge line and goes out to an area called Picinic Point.…
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This trail runs from Barker Branch Road to Trail 1 in the park. This trail circles around the view of the lake and the dam area. The trail travels downward away from a paved road…
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Trail 5 is an easy trail that leads and shoots of with many other trails. Those trails include 48, 13, 41, 42, 17, 9, 18, and 6. So many trails to choose from off this…
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There are lots to see on this trail. It is a fairly well-maintained gravel road. It does have 2 water crossings, one that is fairly shallow and one that can be over a foot deep.…
Learn more about Clover Bottom Creek Road

This trail is within the boundaries of the Daniel Boone National Forest and travels out of the area of Wind Cave to the Lake Branch area. The trail is somewhat maintained with the branches and…
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This trail is a short loop off of Trail 4. This trail travels around and beside an old oil pump. The trail then goes down and beside Sand Lick Fork. The creek that flows through…
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This is the main trailhead that leads into the park from the General Store, the Main Parking Lot, and other Camping and Parking Lots. The trail starts on gravel and is mostly dirt and gravel.…
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This trail is within the boundaries of the Daniel Boone National Forest and travels out of the area of Turkey Foot Campground and Wind Cave. The trail is somewhat maintained with the branches and trees…
Learn more about Big Branch 3044

New Virginia Ridge Road is part of the Daniel Boone Backcountry Byway. This trail is rated easy to moderate, with nothing on the trail providing much of a challenge for a stock Jeep or equivalent…
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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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