Beginner Off-Road Trails Near Sleepy Hollow, Wyoming
Weston Hills
Exceptionally beautiful scenery and rock formations with abundant wildlife to spot along the way. Some areas can be challenging if there are oncoming vehicles due to blind transitions on the steep grades. There are additional… Learn more about Weston Hills
Total Miles
7.7
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
DJ 220
This is an easy and slow drive with a few hills to climb along the way. Most of the hills could get very difficult if there is any measurable amount of rain. Towards the end… Learn more about DJ 220
Total Miles
14.3
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
Bear Lodge
Bear Lodge is an easy well maintained road for Jeeps, SUVs, Overlanders and horse trailers. 4x4 might be needed in the spring, as there might still be snow and mud. Any vehicle, without four-wheel-drive, may… Learn more about Bear Lodge
Total Miles
8.5
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Reanus Cone Trail Part 1
The Reanus Cone Trails are winding single tracks that lead through the mixed pine of the Custer National Forest to a couple of immense meadows. In these high meadows, you might see Wild Turkeys, a… Learn more about Reanus Cone Trail Part 1
Total Miles
4.2
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Reanus Cone Trail Part 2
Reanus Cone Road is a single-lane wide dirt track that leads up and over the Reanus Cone, a geological feature in Powder River County, MT. This road weaves upward through beautiful pines and grassland to… Learn more about Reanus Cone Trail Part 2
Total Miles
3.2
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Ten Mile Creek Road
Ten Mile Creek Road is a single-lane red dirt road that rolls through pasture, meadow, and the dense pines of the Custer National Forest. There are no obstacles on this road, though some sections of… Learn more about Ten Mile Creek Road
Total Miles
5.4
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Hole In the Wall Overlook
This 40-mile trail starts in Kaycee, Wyoming, right off of I-25, and takes you to the canyon rim overlooking the Hole in the Wall Valley and Hole in the Wall Pass. You can stage in… Learn more about Hole In the Wall Overlook
Total Miles
31.6
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Lemonade Road Pt 2
The Southern section of Lemonade Road is a single-lane dirt road that heads uphill (North) toward the heart of the Custer National Forest. While rough and well-traveled, the road has no obstacles on it, though… Learn more about Lemonade Road Pt 2
Total Miles
3.2
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Cement Ridge Fire Lookout
Leaving Spearfish Canyon from Savoy, you'll find yourself on Roughlock Falls Road, a well-maintained gravel road that leads you up to Cement Ridge Fire Lookout, which boasts expansive views of the Black Hills Forest and… Learn more about Cement Ridge Fire Lookout
Total Miles
11.5
Tech Rating
2
Easy
Best Time
Su / Fa
Drop Tube Part 1
Drop Tube Trail is a rolling single track through large open fields of the Custer National Forest. With beautiful open vistas and large meadows, the views are incredible. On this trail there are no obstacles… Learn more about Drop Tube Part 1
Lemonade Road is a red dirt road that winds and weaves its way up, over, around, and through a section of the Custer National Forest. There are no obstacles on this single-lane wide road, and… Learn more about Lemonade Road Part 1
Total Miles
7
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Boundary Gulch
Boundary Gulch trail is a Black Hills favorite for off-road enthusiasts of all kinds. The trail leads you to the Cement Ridge Fire lookout. Along the way, you will find ponds, scenic outlooks and the… Learn more about Boundary Gulch
Total Miles
3.4
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Drop Tube Part 2
Drop Tube Trail is a rolling single track through large open fields of the Custer National Forest. With beautiful open vistas and large meadows, the views are incredible. On this trail, there are no obstacles… Learn more about Drop Tube Part 2
Total Miles
1.7
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Crazy Woman Canyon Road
The canyon is a spectacular sight, and one of the best nature attractions in Northeast Wyoming. The road that winds through the canyon is lined with steep cliffs on both sides and immense boulders. Crazy… Learn more about Crazy Woman Canyon Road
Total Miles
4.6
Tech Rating
2
Easy
Best Time
Fa / Su / Sp
Slip Road
This beautiful drive connects the southern Bighorn National Forest to the small community of Mayoworth. The road's steep grades are almost as impressive as the scenery. Up high, you'll pass patchy forests, broad meadows, and… Learn more about Slip Road
Total Miles
35.6
Tech Rating
3
Moderate
Best Time
Su / Fa
Tinton Road
This is a great way to access trails in the area. It is a wide gravel road with several unloading areas. The traffic can get heavy at times. Beware of dust and wash boards. Learn more about Tinton Road
Total Miles
24.6
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
Kingsbury/Todd Cabin to Hazelton Road
This trail goes through beautiful Bighorn Mountain meadows. There are numerous camping sites...just park your camper anywhere and stay for 2 weeks for free. You won't see neighbors anywhere close, and you're very likely to… Learn more about Kingsbury/Todd Cabin to Hazelton Road
Total Miles
5.1
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Summit Road(FS 265)
This trail leads from Boles Canyon Road to the Summit Ridge cabin and fire lookout. Great views and a good picnic spot. Learn more about Summit Road(FS 265)
Total Miles
3.4
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
FSR 47781
Montana Road 47781 isn't much of one at all, but more like a rutted track through the high grassland of Montana. With views of buttes and forest, the road proved challenging after rain and snow,… Learn more about FSR 47781
Total Miles
1.1
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
FSR 47782
Montana Road 47782 is a rutted, mud track that meanders through the Montana countryside and Custer National Forest. This road isn't much of one at all, but more like a rutted track through the high… Learn more about FSR 47782
Total Miles
1.1
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
Red Top Hill Road
Red Top Hill road is a single-lane rock road leading to the Tarter Ranch at its terminus. This beautiful road winds and rolls to the South, giving tremendous vista views of Montana's prairies and buttes… Learn more about Red Top Hill Road
Wilbur Creek Cutoff Road is a beautiful relaxing trail that gently meanders through the rolling hills of the Custer National Forest. You'll see mule deer and cattle grazing along this road as well as groves… Learn more about Wilbur Creek Cutoff Road
Total Miles
4.7
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
FSR 47792
Montana Road 47792 is a rutted, mud track that meanders through the Montana Countryside and Custer National Forest. This road isn't much of one at all, but more like a rutted track through the high… Learn more about FSR 47792
Total Miles
4
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
Canyon Rim
This trail system off Tinton Road will give you hours of fun. With 4 main loops, you travel through some of the best the Black Hills has to offer. Before or after riding you can… Learn more about Canyon Rim
Total Miles
9.2
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
Sheep Mountain Fire Lookout Tower
From Highway 16, west of Buffalo, you take the Sheep Mountain Road to the lookout. It's an easy ride with spectacular views at the top. The fire lookout facility sits at 9600 feet in the… Learn more about Sheep Mountain Fire Lookout Tower
Total Miles
16.8
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
Game Farm
Game farm is a local favorite in the Spearfish Area. The area is a game preserve for the South Dakota Fish and Game Department. It can be accessed from Higgins Gultch Road, or from Tinton… Learn more about Game Farm
Total Miles
7
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
South Big Horn/Red Wall Scenic Backway
This designated Wyoming Scenic Backway makes a large semi-loop through the vastness of north-central Wyoming. It's a remarkable drive that crosses more than a hundred miles while catching the southern tail of the Bighorn Mountains.… Learn more about South Big Horn/Red Wall Scenic Backway
Total Miles
94.8
Tech Rating
3
Easy
Best Time
Su / Fa
Outlaw Cave
An easy 9-mile trail, using gravel roads leading to the Outlaw Cave Campground/parking area. From Kaycee, take Mayoworth Road west to Barnum Road. Take Barnum Road south to where it turns into dirt. You can… Learn more about Outlaw Cave