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.
Last updated: May 17, 2026
60
riders
19.9km
00:53
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
10
riders
65.3km
03:11
850m
850m
Moderate road ride. Good fitness required. 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.
8
riders
59.1km
02:36
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
89.5km
04:53
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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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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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