5.0
(4)
15
riders
3
rides
Touring cycling in Lovers Leap State Park and its vicinity offers routes through the scenic Housatonic River valley, characterized by rolling hills and diverse woodlands. While the park itself is primarily known for hiking, the surrounding area provides opportunities for touring cyclists to explore a mix of paved and unpaved surfaces. The landscape features dramatic vistas overlooking the river gorge and historic elements like the 1895 Berlin Iron Bridge.
Last updated: June 28, 2026
5.0
(4)
5
riders
49.6km
03:08
370m
370m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
33.4km
02:08
410m
410m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
37.9km
02:34
430m
430m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.
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Explore the Rock Tunnel, a 235-foot passage from the Shepaug Valley Railroad (1872-1948). It's a blast to go under during your hike, giving you a taste of the area's cool railroad history.
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This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.
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A short 235 foot tunnel that was built as part of the Shepaug Valley Railroad that ran from 1872 to 1948. Make sure you have your lights on going through the tunnel!
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The touring cycling routes in the vicinity of Lovers Leap State Park are characterized by scenic roads that navigate through rolling hills and diverse woodlands. You'll encounter a mix of paved and unpaved surfaces, offering varied experiences for different fitness levels. The area also features dramatic vistas overlooking the Housatonic River valley.
Yes, the area is rich in natural beauty and historical landmarks. You can expect breathtaking panoramic views of the Housatonic River valley. A notable historical feature is the 1895 Berlin Iron Bridge, one of the few remaining iron lenticular truss bridges in Connecticut. Routes like the Bulls Bridge loop from Sherman will take you past the historic Bulls Bridge.
The touring cycling routes in the Lovers Leap State Park area offer a range of difficulties. Most routes are classified as moderate, such as the Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury and the Bulls Bridge loop from Sherman. There are also more challenging options available, like the Leonard Pond – Hatch Pond loop from Sherman, which covers a longer distance and has significant elevation gain.
Yes, several touring cycling routes in the area are designed as loops. For instance, the Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury, the Bulls Bridge loop from Sherman, and the Leonard Pond – Hatch Pond loop from Sherman are all circular routes, allowing you to start and end at the same point.
While Lovers Leap State Park itself permits leashed dogs on its hiking trails, the suitability for dogs on specific touring cycling routes can vary. Generally, if you are cycling on public roads or designated multi-use paths outside the immediate park boundaries, leashed dogs are often permitted. Always ensure your dog is comfortable with the distance and terrain, and check local regulations for any specific route you plan to take.
The region around Lovers Leap State Park is particularly vibrant during the fall foliage season, offering breathtaking panoramic views. Spring and summer also provide pleasant conditions for cycling through the woodlands and along the Housatonic River. Always check local weather conditions before heading out.
While the park itself is primarily known for hiking, the surrounding area offers various touring cycling routes. The guide features routes that are generally moderate in difficulty, which might be suitable for families with older children or those accustomed to longer rides. For very young children, paved paths and scenic bridges within certain accessible areas of the park might be more appropriate for casual cycling.
Specific parking information for each touring cycling route is typically available on the individual route pages on komoot. Generally, you can look for parking areas near the suggested starting points of the routes, such as in Roxbury or Sherman, depending on the specific tour you choose.
Touring cyclists appreciate the scenic beauty of the Housatonic River valley, the rolling hills, and the diverse woodlands that characterize the routes. The komoot community has highly rated the routes in this area, often praising the varied terrain and the opportunity to explore both natural landscapes and historical elements like the 1895 Berlin Iron Bridge.
Yes, the Leonard Pond – Hatch Pond loop from Sherman is a touring cycling route that leads through woodlands and past local ponds, offering serene views of these water features.
The longest touring cycling route featured in this guide is the Leonard Pond – Hatch Pond loop from Sherman, which spans 37.1 miles (59.6 km) and typically takes about 3 hours and 40 minutes to complete.
Many routes in the Lovers Leap State Park area offer views of the Housatonic River valley. The park itself provides stunning views of the river gorge, and touring cycling routes in the vicinity are designed to showcase the scenic beauty of the river and its surroundings.


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