5.0
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Gravel biking in Lovers Leap State Park offers diverse terrain across a rugged ridge with panoramic views of the Housatonic River and surrounding hills. The park features dense forests, rocky outcrops, and tranquil creek beds, providing a varied landscape for cyclists. Routes incorporate a mix of gravel roads, hard-packed gravel, asphalt, and dirt roads, traversing areas like the Housatonic Gorge and overlooking Lake Lillinonah. This region provides engaging experiences for gravel cyclists seeking natural beauty and varied surfaces.
Last updated: September 29, 2026
16
riders
126km
07:36
1,630m
1,630m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
riders
106km
06:02
1,330m
1,330m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5
riders
63.6km
03:52
820m
820m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
43.7km
02:50
790m
790m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
38.6km
02:36
730m
730m
Hard gravel ride. Very good fitness required. You may need to push your bike for some segments of this route.
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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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This is a tiny but highly scenic little park. The roads that circumnavigate Lake Warmaug are partially shaded and go right up to the water's edge, and the views out across the water are especially beautiful in the autumn. There is also camping, hiking, and kayaking here, as well as a couple small beaches for swimming.
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The Mine Hill Preserve covers 360 acres and include the remnants of a 19th century iron making facility, which is now on the National Register of Historical Places. A series of signs along the paths give you the details of iron making process from mining the ore to processing steel.
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This part of Upper Grassy Hill Road runs parallel to this small grass airstrip with its old hangar, where you might catch sight of a plane.
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This small lake-side park comes equipped with picnic benches and plenty of trees to provide shade on a summers day. A great spot to take a break.
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The Natalie White Preserve is one of many such preserves overseen by the Roxbury Land Trust. Though small there is a short trail leading to a hilltop that affords nice views of the areas and makes for a good picnic spot.
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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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There are over a dozen dedicated no-traffic gravel bike trails in and around Lovers Leap State Park. These routes offer a mix of moderate and difficult options, ensuring a suitable ride for various skill levels.
The trails in Lovers Leap State Park feature diverse terrain, including gravel roads, hard-packed gravel, asphalt sections, and dirt roads. You'll encounter dense forests, rocky outcrops, and tranquil creek beds, often with significant elevation changes.
Yes, many of the gravel bike routes in the Lovers Leap State Park area are designed as loops. For example, you can explore the challenging River Trail – Tracy Road Gravel Route loop from New Milford, which covers over 126 km, or the shorter, moderate Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury.
Many routes offer stunning views of the Housatonic River and Lake Lillinonah. You'll also encounter historical features like the iconic 1895 Berlin Iron Bridge, known as the Lovers Leap Bridge, and various historical ruins, including remnants of an old estate and a castle ruin, adding a unique historical dimension to your ride.
Lovers Leap State Park is particularly beautiful during the fall foliage season, when the surrounding hills are vibrant with color. Spring and summer also offer pleasant conditions, though summer can be warm. Winter biking is possible, but be prepared for colder temperatures and potential snow or ice on trails.
While many routes in the immediate vicinity are rated difficult, there are moderate options that might be suitable for families with older, experienced riders. The Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury is a moderate 21 km loop that could be a good starting point for those looking for a less strenuous ride.
Gravel bike trails in Lovers Leap State Park vary significantly. You can find shorter, moderate routes around 20-25 km with a few hundred meters of elevation gain, such as the Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury. Longer, more challenging routes can extend over 100 km with more than 1500 meters of climbing, like the River Trail – Bulls Bridge loop from New Milford.
Yes, Lovers Leap State Park is home to various wildlife. Cyclists often spot birds, deer, and small mammals along the trails, especially during quieter times of the day. The park's diverse woodlands provide a rich habitat for these creatures.
Absolutely. Experienced riders seeking a significant challenge will find several long-distance routes. The Lake Waramaug State Park – River Trail loop from New Milford offers a demanding 63.5 km ride with over 800 meters of elevation, while the River Trail – Tracy Road Gravel Route loop from New Milford is an epic 126 km journey with over 1600 meters of climbing.
The unique blend of challenging terrain, historical landmarks like the Lovers Leap Bridge and various ruins, and the stunning panoramic views of the Housatonic River and Lake Lillinonah set Lovers Leap State Park apart. The park's natural beauty, especially during fall, combined with its rich folklore, creates a memorable gravel biking adventure.


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