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Routes
Road cycling routes
United States
Connecticut
Northwest Hills Planning Region

New Milford

The best road cycling routes around New Milford

4.5

(2)

177

riders

38

rides

Road cycling around New Milford, Connecticut, offers diverse terrain characterized by rolling hills, expansive lakes, and the Housatonic River. The region features a mix of well-paved roads and some unpaved segments, providing varied cycling experiences. Cyclists can find routes with gentle gradients around lakes or more challenging paths with significant elevation changes through forested areas. This landscape provides a scenic backdrop for road cycling, accommodating different fitness levels.

Best road cycling routes around New Milford

  • The most popular road cycling…

Last updated: May 17, 2026

60

riders

#1.

Lake Waramaug State Park – Lake Waramaug loop from Marbledale

19.9km

00:53

200m

200m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. 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

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

Moderate

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard
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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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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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Jamie S.
January 17, 2024, Jones Pond

Jones Pond is a small pond just off of Lakeside Road. This is a pretty place to slow down a little and look out over the water.

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From 1903 to 1942, the site served as the rural campus of Columbia University's Engineering Department. Imagine students learning surveying, mining, and other practical skills amidst the serene Connecticut countryside.

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Alex
December 30, 2023, Bantam Swamp

Bantam Swamp is around and predominately south of Little Pond. It is a wetland teeming with wildlife, and it is a picturesque area to visit.

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Frequently Asked Questions

How many road cycling routes are available in New Milford?

New Milford offers over 40 road cycling routes, providing a diverse range of options for cyclists of all abilities. These routes vary in difficulty, from easy loops around lakes to more challenging rides with significant elevation changes.

What kind of terrain can I expect on road cycling routes in New Milford?

The terrain around New Milford is characterized by rolling hills, expansive lakes, and the Housatonic River. You'll find a mix of well-paved roads, with some routes incorporating unpaved segments that are generally passable with road bikes if navigated carefully. Elevation gains range from less than 1,000 feet on easier rides to over 3,000 feet on more challenging routes.

Are there any easy, beginner-friendly road cycling routes in New Milford?

Yes, New Milford has several easy routes perfect for beginners or those seeking a relaxed ride. A great option is the Lake Waramaug State Park – Lake Waramaug loop from Marbledale, which is 12.4 miles long and offers scenic views with minimal elevation gain. Another easy route is the Lake Waramaug – Lake Waramaug State Park loop from Washington, providing extensive lake views over 25.4 miles.

What are some challenging road cycling routes in the New Milford area?

For cyclists looking for a challenge, New Milford offers routes with significant climbs and longer distances. The Lake Waramaug State Park – Lake Waramaug loop from Washington, at 40.6 miles with over 2,800 feet of elevation gain, provides a good workout through rolling hills. Another moderate option is the Squantz Pond – Squantz Pond loop from Candlewood Mountain, covering 35 miles with similar elevation.

What natural features and landmarks can I see along the road cycling routes?

Many routes offer stunning views of the region's natural beauty. You can cycle alongside the picturesque Housatonic River, or enjoy the expansive waters of Candlewood Lake and Lake Lillinonah. Routes around Lake Waramaug provide beautiful lake views, especially during autumn. Notable landmarks and natural features include Lake Waramaug State Park and Squantz Pond State Park. You might also encounter the River Trail and the historic Quarry Bridge.

Are there any circular road cycling routes in New Milford?

Yes, many of the road cycling routes in New Milford are designed as loops, allowing you to start and end at the same point. Popular circular routes include those around Lake Waramaug, such as the Lake Waramaug State Park – Lake Waramaug loop from Marbledale, and the Squantz Pond – Squantz Pond loop from Candlewood Mountain.

What is the best time of year for road cycling in New Milford?

The spring, summer, and especially autumn months are ideal for road cycling in New Milford. Spring brings lush greenery, while summer offers warm weather for longer rides. Autumn is particularly stunning, with vibrant fall foliage providing a picturesque backdrop, especially around Lake Waramaug. Winter cycling is possible but requires appropriate gear due to colder temperatures and potential for snow or ice.

What do other road cyclists enjoy most about cycling in New Milford?

The road cycling routes in New Milford are highly rated by the komoot community, with an average score of 4.5 stars. Cyclists frequently praise the region's diverse terrain, from scenic lake loops to challenging climbs, and the beautiful natural landscapes, including views of the Housatonic River and expansive lakes.

Are there options for family-friendly road cycling in New Milford?

While specific dedicated family-friendly road cycling trails are not highlighted, the easier, shorter loop routes with less elevation, such as the 12.4-mile Lake Waramaug State Park – Lake Waramaug loop from Marbledale, can be suitable for families with older children who are comfortable on roads. Always prioritize safety and choose routes with lower traffic.

Where can I find parking for road cycling routes in New Milford?

Many popular cycling areas, especially around state parks like Lake Waramaug State Park and Squantz Pond State Park, offer designated parking facilities. For routes starting in or near towns, street parking or public lots may be available. It's advisable to check specific route details or local town information for the most convenient parking options.

Are there any cafes or pubs along the road cycling routes in New Milford?

New Milford's charming historic downtown and surrounding areas offer various amenities. While specific cyclist-friendly establishments aren't listed for every route, you can often find cafes, pubs, and restaurants in the town center or nearby villages. For example, the Fife 'n Drum Restaurant & Inn loop from Sherman suggests a potential stop along its route.

Does New Milford offer connections to larger cycling networks?

Yes, New Milford is strategically located to connect with broader cycling networks. The planned New Milford River Trail is set to become part of the Western New England Greenway, a multi-state network of on-road bike routes. This includes US Bike Route 7, which follows the Route 7 Corridor, offering opportunities for longer-distance cycling adventures.

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