Lovers Leap State Park
Lovers Leap State Park
4.0
(1)
44
riders
14
rides
Road cycling routes in Lovers Leap State Park are situated in a region characterized by a rugged ridge overlooking the Housatonic River and Lake Lillinonah. The surrounding New Milford area features an extensive network of paved, low-traffic roads that traverse rolling hills and woodlands. While the park's interior trails are multi-use, the external roads provide continuous views of the river valley and connect to broader cycling routes. This landscape offers varied terrain suitable for road cyclists.
Last updated: July 12, 2026
7
riders
89.5km
04:54
1,620m
1,620m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4
riders
19.0km
00:55
210m
210m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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8
riders
56.5km
02:50
790m
790m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
4
riders
31.0km
01:37
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
52.1km
02:15
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Lovers Leap State Park
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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Harrybrooke Park is a hidden gem in an ideal setting near the river. In addition to the lovely surroundings the the Historic Harden House Museum is open to visitors.
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Disbrow Pond is a small body of water just off the side of Sawmill Road. You get a pretty great view from the bridge crossing over the water, but you can hop off the bike and go down next to the water if you pull into the entrance on the north side of the reservoir.
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Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.
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Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.
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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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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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The road cycling routes in the Lovers Leap State Park region primarily feature paved, low-traffic roads that traverse rolling hills and woodlands. You'll experience varied terrain, with some routes offering extensive views of lakes and others leading through scenic river valleys.
While the guide lists routes with moderate and difficult ratings, the broader New Milford area and sections of the Housatonic Covered Bridge Bicycle Trail are known for utilizing riverside roads with generally few hills, making them enjoyable for less experienced road cyclists. Many routes are on existing publicly maintained paved roads.
Road cycling in this region offers continuous views of the Housatonic River valley and the rolling hills of Connecticut. You can expect to see dramatic vistas, especially from roads near the park, and the historic 1895 Berlin Iron Bridge is visible from nearby routes. Routes like Squantz Pond – Squantz Pond loop from Candlewood Mountain provide scenic views of Squantz Pond, while others showcase the picturesque landscapes of the Housatonic River and Lake Lillinonah.
Yes, many of the road cycling routes in the area are loops. For example, the Lake Warmaug State Park – Lake Waramaug loop from New Milford is a challenging circular route, and the Harrybrooke Park loop from Brookfield offers a moderate, shorter option through woodlands and local parks.
For experienced riders seeking a longer challenge, the Lake Warmaug State Park – Lake Waramaug loop from New Milford is a difficult 55.6-mile (89.5 km) route that takes nearly 5 hours to complete, offering extensive views and significant elevation changes.
While specific parking for road cycling routes isn't detailed, the Lovers Leap State Park itself has an entrance on Still River Drive, which connects to broader paved routes. The New Milford area, which serves as a starting point for many routes, typically offers various parking options within the town or near trailheads that access the Housatonic River Valley cycling network.
The region is particularly vibrant during the fall foliage season, offering breathtaking panoramic vistas. Spring and summer also provide pleasant conditions for road cycling, with lush greenery and comfortable temperatures. It's always a good idea to check local weather conditions before heading out.
The road cycling routes in Lovers Leap State Park are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the scenic views of the Housatonic River valley, the low-traffic paved roads, and the varied terrain that offers options for different skill levels.
The road cycling network in the Housatonic River Valley connects to charming towns like New Milford. These towns typically offer cafes, restaurants, and other amenities where cyclists can stop for refreshments. Routes starting from or passing through these areas will provide opportunities for breaks.
There are over 10 road cycling routes available in the Lovers Leap State Park region, with options ranging from moderate to difficult in terms of challenge.
Yes, several routes in the area feature beautiful lakes and ponds. The Lake Warmaug State Park – Lake Waramaug loop from New Milford offers extensive views of Lake Waramaug, and the Squantz Pond – Squantz Pond loop from Candlewood Mountain provides scenic views of Squantz Pond.
Many of the routes utilize low-traffic, paved roads, which can be suitable for families with older children who are comfortable with road cycling. The New Milford River Trail, with its paved sections alongside the Housatonic River, offers a flat and scenic ride that could be a good option for families.


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