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Routes
Road cycling routes
United States
Connecticut
Northwest Hills Planning Region

Lovers Leap State Park

The best road cycling routes in 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.

Best road cycling routes…

Last updated: July 12, 2026

7

riders

#1.

Lake Waramaug State Park – Lake Waramaug loop from New Milford

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.

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Hard

4

riders

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

4.0

(1)

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Lovers Leap State Park

Hiking in Lovers Leap State Park

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Running Trails in Lovers Leap State Park

Cycling in Lovers Leap State Park

Tips from the Community

Zachary
September 3, 2024, Lake Waramaug 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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Andrus
February 25, 2024, Harrybrooke Park

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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Matthew
February 20, 2024, Disbrow Pond

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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Jamie S.
February 20, 2024, Squantz Pond

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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Jamie S.
February 14, 2024, Squantz Pond

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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Caro "Bandit"
February 24, 2022, Bulls Bridge

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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Douglas Nadig
September 26, 2021, Harrybrooke Park

on exit path from park.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in the Lovers Leap State Park area?

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.

Are there road cycling routes suitable for beginners in the Lovers Leap State Park area?

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.

What scenic views or landmarks can I expect to see while road cycling near Lovers Leap State Park?

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.

Are there any circular road cycling routes in the Lovers Leap State Park area?

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.

What are some longer road cycling routes for experienced riders?

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.

Where can I find parking for road cycling near Lovers Leap State Park?

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.

When is the best time of year to go road cycling in Lovers Leap State Park?

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.

What do other road cyclists enjoy most about the routes in Lovers Leap State Park?

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.

Are there cafes or places to stop for refreshments along the road cycling routes?

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.

How many road cycling routes are available in the Lovers Leap State Park region?

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.

Can I find routes that feature lakes or ponds?

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.

Are the road cycling routes around Lovers Leap State Park suitable for families?

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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