61
riders
4
rides
Road cycling in Clifty Wilderness is not permitted within the wilderness boundaries; however, the surrounding Daniel Boone National Forest offers numerous routes. This region is characterized by rugged terrain, high cliffs, and steep valleys, with the Red River bisecting the area. Cyclists can explore routes through dense hemlock forests, hardwoods, and rhododendron thickets, encountering sandstone arches and rock shelters in the broader Red River Gorge area. The landscape provides a challenging environment for road cycling on paved and unpaved roads…
Last updated: July 2, 2026
6
riders
98.9km
04:37
1,150m
1,150m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
45.4km
01:59
420m
420m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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24
riders
61.2km
02:52
720m
720m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
25
riders
67.2km
03:32
670m
670m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
3
riders
52.8km
02:24
560m
560m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Clifty Wilderness
Flowing 97 miles from the Cumberland Plateau to the Kentucky River, the Red River winds through eastern Kentucky’s rugged landscapes and forms the Red River Gorge. Its 1,400-square-mile watershed has deep ravines, sandstone cliffs, and hemlock forests, creating a haven for outdoor recreation. A 19-mile designated Wild and Scenic River segment offers opportunities for paddling, from thrilling rapids in the upper gorge to calm stretches downstream. Anglers will find trout and bass in its cool, clear waters, while hikers and bikers can explore riverside trails, waterfalls, and natural arches. The Red River is both a lifeline for biodiversity and a gateway to unforgettable backcountry adventure.
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This narrow, one-lane tunnel is considered to be the gateway into the Red River Gorge. If you plan on riding through here be sure to have your lights ready as the tunnel it long enough to get very dark in the middle.
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No, road cycling and other mechanized equipment are prohibited within the boundaries of Clifty Wilderness itself. However, the surrounding Daniel Boone National Forest offers excellent road cycling opportunities, and the routes in this guide explore that broader area.
While cycling is restricted within Clifty Wilderness, the broader Daniel Boone National Forest, which encompasses the area, provides numerous roads suitable for road cycling. Our guide features routes that explore the scenic Red River Gorge area, known for its dramatic rock formations and features like the historic Nada Tunnel.
The road cycling routes in this region are generally considered moderate to difficult. You can expect significant elevation changes and challenging climbs. For example, the Nada Tunnel – Red River loop from Hoedown Island is rated difficult, featuring over 1100 meters of elevation gain.
The routes listed in this guide are primarily moderate to difficult, with no easy options. Cyclists should be prepared for challenging terrain and elevation. If you are a beginner, consider shorter sections of these routes or look for flatter options further afield in the Daniel Boone National Forest.
The routes in this region often pass through the Red River Gorge area, offering views of rugged terrain, high cliffs, and sandstone formations. A notable feature is the historic 900-foot Nada Tunnel, which cyclists pass through on routes like the Red River – Nada Tunnel loop from Ash Branch Climbing Area.
Spring and fall generally offer the most pleasant conditions for road cycling, with milder temperatures and beautiful foliage. Summers can be hot and humid, while winters may bring cold temperatures and potential for icy roads, especially in shaded areas.
Yes, all the road cycling routes featured in this guide are loops, allowing you to start and end at the same point. Examples include the Nada Tunnel – Red River loop from Hoedown Island and the Red River – Nada Tunnel loop from Peace of Mind Campground.
Given the rugged terrain and potential for varying weather, it's advisable to pack essentials such as plenty of water, snacks, a repair kit, and appropriate layers of clothing. A helmet is mandatory, and a GPS device or a downloaded komoot tour is highly recommended for navigation, as trails can be less marked in wilderness-adjacent areas.
While the immediate vicinity of the wilderness area is remote, you may find cafes and restaurants in nearby towns and communities within the broader Red River Gorge area. It's always a good idea to plan your stops in advance and carry sufficient provisions, especially for longer rides.
The road cycling routes in this guide vary in length. For instance, the Nada Tunnel – Red River loop from Hoedown Island is approximately 45 km, while the Nada Tunnel – Red River loop from Hoedown Island (the longer version) extends to nearly 98 km.
Road cycling in the Red River Gorge area offers a unique blend of challenging climbs, scenic vistas of dramatic sandstone cliffs and arches, and the experience of riding through the historic Nada Tunnel. The region's rich biodiversity and designation as a National Wild and Scenic River add to its distinctive character.

