This wooded, mountain road is an easy gravel bypass. The road takes you by the Wildcat Mountain Civil War monuments and battlefield. It's a very beautiful drive and full of history. Learn more about Rockcastle Exploring River Bypass
Total Miles
3.1
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
Daughtry to Sheltowee Trace
Daughtry ln starts out as a nice gravel road for about 2 miles. There's a couple creek crossings which one can get deep and fast moving. Once you've crossed the creek you'll go through a… Learn more about Daughtry to Sheltowee Trace
Total Miles
6.7
Tech Rating
4
Moderate
Best Time
Sp / Su / Fa / Wi
Rock Lick / Pipeline Exit
This is a very scenic trail that runs along and through Rock Lick Creek. There are multiple creek crossings, as well a few deep and off-camber mud holes. Most of the deep mud holes have… Learn more about Rock Lick / Pipeline Exit
Total Miles
5.3
Tech Rating
6
Moderate
Best Time
Sp / Su / Fa / Wi
KAT Hard 2
This is a 1000-mile scenic loop through Kentucky, Tennessee and West Virginia. This is one of the harder sections. It's an awesome section with lots of mud, but most of the mud holes have a… Learn more about KAT Hard 2
Total Miles
8
Tech Rating
6
Moderate
Best Time
Sp / Su / Fa / Wi
Pistol Creek
This is a great, 19-mile loop that takes you through a rocky creek beds and some fun obstacles. It is a scenic drive overlooking the Kentucky River. Learn more about Pistol Creek
Total Miles
17.9
Tech Rating
5
Moderate
Best Time
Sp / Su / Fa / Wi
Henry Mountain Road
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… Learn more about Henry Mountain Road
Total Miles
4.2
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
New Virgina Ridge Rd to Hidden Lake
This is a nice trail that takes you to a secluded pond. It is a great spot to camp and fish. There are some low hanging branches to watch out for, and some muddy spots… Learn more about New Virgina Ridge Rd to Hidden Lake
Total Miles
2.7
Tech Rating
4
Moderate
Best Time
Su
Lake Trail
This is a little shortcut to get to a hidden lake. It has a couple of rocky spots with a small sandstone incline. You can tie this from New Virginia Ridge Road to bypass some… Learn more about Lake Trail
Total Miles
0.5
Tech Rating
4
Moderate
Best Time
Sp / Su / Fa / Wi
Sinking Creek
Sinking Creek is a very scenic trail that features large rock walls and a few springs that feed out of the rock. The large variety of plant life almost makes it seem tropical in the… Learn more about Sinking Creek
Total Miles
1.8
Tech Rating
6
Moderate
Best Time
Sp / Su / Fa
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… Learn more about Bald Rock Fork Rd
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… Learn more about Cave Fork Rd DBBB
Total Miles
2.7
Tech Rating
2
Easy
Best Time
Su
No Man's Overlook
Beautiful overlook of the area. This trail has been recently graded so its nice and flat. There could be some lose dirt and mud when wet. Be cautious when up here as there is no… Learn more about No Man's Overlook
Total Miles
3.2
Tech Rating
6
Moderate
Best Time
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. Learn more about Wentworth School Rd
Total Miles
2.5
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
Mountain Springs Road
Mountain Springs Road is a challenging track through a thick forest with lots of mud and ledges. There is a small rock garden towards the southern end of the trail. This route starts at the… Learn more about Mountain Springs Road
Total Miles
1.8
Tech Rating
6
Moderate
Best Time
Sp / Su / Fa / Wi
Trail 15 Hollerwood Park
This trail is Green Trail 15 at Hollerwood Offroad Park. It intersects with several Green, Blue, and Black trails. Some OPTIONAL difficult rock pinch (tight squeeze) points along the way but have bypasses maintaining its… Learn more about Trail 15 Hollerwood Park
Total Miles
0.9
Tech Rating
3
Easy
Best Time
Sp / Su / Fa / Wi
Old Fincastle Rd
This is a short trail with one difficult obstacle at the end. It is a mild trail to a deep creek crossing. Then a little off-camber dirt trail to the main event. Old Fincastle is… Learn more about Old Fincastle Rd
Total Miles
3
Tech Rating
7
Difficult
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… Learn more about Fixer Rd DBBB
Total Miles
2
Tech Rating
3
Easy
Best Time
Sp / Su / Fa / Wi
Walkers Creek
This is a really fun and beautiful trail. It starts with a rocky decent to a deep water crossin,g and then a long, straight stretch. There are several puddles with a solid bottom. Once you… Learn more about Walkers Creek
Total Miles
5
Tech Rating
6
Moderate
Best Time
Su
Sand Lick Rd
This is a dirt and gravel road with large ruts and deep puddles. It is a very scenic trail with a few side trails to explore. There are some creek crossings, as well a place… Learn more about Sand Lick Rd
Cowen Creek is a very beautiful trail. It follows a creek bed with rocks and mud holes to navigate. There are two waterfalls to climb. This trail requires high clearance. Learn more about Cowen Creek
Total Miles
2.1
Tech Rating
7
Difficult
Best Time
Sp / Su / Fa
Spaas Creek
Spaas Creek is a wonderful 6-mile creek ride east of Winchester. It is located inside the Daniel Boone National Forest and is a short distance from many other rides in the area. The northern trailhead… Learn more about Spaas Creek
Total Miles
5.6
Tech Rating
5
Moderate
Best Time
Sp / Su
Cold Iron Fork Road
This is an easy trail with a couple moderate sections. Not recommended when conditions are wet, as it can become very slick and rutted. The trail has lots of character with wild roses and plenty… Learn more about Cold Iron Fork Road
Total Miles
2.5
Tech Rating
7
Difficult
Best Time
Sp / Su / Fa
Trail 19 - Walnut Mountain Trail
This is a long mountain road that is almost all single track along the side of the mountains with beautiful views throughout the trail. There are lots of humps and dips that make it a… Learn more about Trail 19 - Walnut Mountain Trail
Total Miles
8.4
Tech Rating
6
Moderate
Best Time
Sp / Su / Fa / Wi
Elk Viewing Tower Road - Trail 25
This is a well-maintained gravel road that goes from Highway 25W to the elk viewing tower at Hatfield Knob. There are several viewing areas and lookouts on the way up as well, so keep an… Learn more about Elk Viewing Tower Road - Trail 25
Total Miles
4.3
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Trail 37 - Hickory Creek Trail
This trail is a wide rocky trail with small mud holes, transitioning to a single-track trail with longer mud holes, rocks, and water crossings near the end. At the end of the trail, you are… Learn more about Trail 37 - Hickory Creek Trail
Total Miles
3.1
Tech Rating
5
Moderate
Best Time
Sp / Su / Fa / Wi
Trail 13 - Lee Asbury Road
This trail starts on the south end as a wide dirt road that can be traversed in most stock vehicles. It remains this way until you get to around Broyles Cemetary. Towards the north end,… Learn more about Trail 13 - Lee Asbury Road
Total Miles
7.9
Tech Rating
4
Moderate
Best Time
Sp / Su / Fa / Wi
McCormick Cemetery Road - Trail 24
This trail is a maintained gravel road that connects several other popular trails. At one end it connects to Trail 19, and at the other end, it connects to Trail 25. Trail 37 is also… Learn more about McCormick Cemetery Road - Trail 24
Total Miles
3.9
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Bandy Creek Trek
This is a combination of dirt, gravel, and single-track in-the-woods roads. There really aren't a lot of difficult obstacles to make a note of other than a few areas that are washed out on Duncan… Learn more about Bandy Creek Trek
Total Miles
4.9
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
Trail 6 - Short Mountain Trail
This is a one-lane mountain road with steep climbs, ruts, and mud holes. There are places to pass and bypasses around most of the big mud holes. There is one mud pit with a steep… Learn more about Trail 6 - Short Mountain Trail