4.6
(43)
594
riders
65
rides
Touring cycling around New Milford offers a diverse landscape of rolling hills, dense forests, and river-carved paths. The region features a developing greenway network, including sections of the New Milford River Trail Greenway, which enhances cycling opportunities. The Housatonic River is a prominent natural feature, with many routes running alongside it. This varied terrain provides options for different cycling abilities.
Last updated: May 15, 2026
18
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(2)
8
riders
43.2km
02:33
240m
240m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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7
riders
89.2km
05:14
470m
470m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
6
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
15.2km
01:01
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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There is a memorial, playground, and trailhead for Rockleigh Woods behind the Volunteer Fire Department.
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The Oradell Reservoir is an important source of clean drinking water to around 750,000 people. Built up over the early 1900s and completed in 1923, it’s now protected as a Category 1 water source, meaning it’s some of the purest in the state. It is a critical part of the region’s infrastructure and a reminder of how closely nature and community are connected.
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The majority of the river courses through popular suburban areas. It earns its name from a river in Scotland near Saddell. This section of the river winds its way through several parks, offering a delightful view of the flowing waters from this point.
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The Oradell Dam forms this freshwater reservoir, which feeds the Lower Hackensack River. Created to supply drinking water to over 800,000 people, it holds 29.4 billion gallons of water. This spot offers a nice view of the crystal-clear water.
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Nice view of the Tarrytown Reservoir. The trail runs very close to the water, so you have a wonderful, unobstructed view across the reservoir. The path is popular with cyclists, so make sure you move to the edge if you want to stop to enjoy the great vistas.
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New Milford offers a wide variety of touring cycling routes, with over 70 options available. These routes cater to different skill levels, including 22 easy, 38 moderate, and 10 difficult trails.
The diverse landscape of New Milford makes it appealing for touring cycling throughout much of the year. However, the fall foliage season is particularly vibrant, offering picturesque views. Spring and early summer also provide pleasant conditions before the peak heat, while the winter months may present challenges due to snow and ice on some trails.
The touring cycling routes in New Milford are highly rated by the komoot community, with an average score of 4.6 stars from over 140 reviews. Cyclists often praise the region's diverse landscape, which includes rolling hills, dense forests, and scenic river-carved paths, as well as the developing greenway network.
Yes, New Milford has several routes suitable for beginners and families. The Saddle River Pathway – Wild Duck Pond loop from Anderson Street is a moderate option that offers a scenic loop experience. Additionally, sections of the New Milford River Trail Greenway, particularly the paved quarter-mile Riverwalk at Young's Field Park, are flat and easy, ideal for a relaxed family ride.
Absolutely. For experienced cyclists seeking a challenge, New Milford offers routes with significant elevation gains. The The High Bridge – Hudson River Drive loop from River Edge is a difficult 52.7-mile path featuring substantial climbing and river views. Another demanding option is the Hudson River Drive – 9W Market loop from Oradell, a 66.2-mile trail through scenic roadways.
The New Milford River Trail Greenway features varied terrain. Currently, a five-mile section from Boardman Road north to Gaylordsville is primarily gravel and dirt, following the Housatonic River corridor and generally easy to ride. There's also a paved quarter-mile section at Young's Field Park, known as the Riverwalk, which is flat and runs alongside the Housatonic River.
Many routes in New Milford run alongside the prominent Housatonic River, offering scenic views. You can also find several viewpoints and natural monuments in the area. For example, Point Lookout and Alpine Lookout offer panoramic vistas. The region also features several beautiful lakes, such as Oradell Reservoir and Wild Duck Pond, which can be enjoyed from nearby trails.
Yes, many touring cycling routes in New Milford are designed as loops, providing a convenient way to start and end your ride at the same point. An example is the Small Water Jewel – Joseph B. Clarke Rail Trail loop from Dumont, a moderate 43.1 km trail. The Oradell Reservoir – Piermont Railway Station (historic) loop from Oradell is another popular moderate loop option.
Yes, the region offers historical points of interest. The Boardman Bridge, a historic lenticular truss structure built in 1888 and listed on the National Register of Historic Places, is located near the northern section of the New Milford River Trail. The Housatonic Bike Trail also utilizes less-traveled, rural roadways that pass through small villages, offering glimpses into the area's past.
New Milford boasts several parks and green spaces that enhance the cycling experience. The New Milford River Trail Greenway passes through Saga Meadows Park and includes the Riverwalk at Young's Field Park. Other notable parks include Lover's Leap State Park, Squantz Pond State Park, Lake Waramaug State Park, Carlson's Grove Park, Harrybrooke Park, Baldwin Park, and Clatter Valley Park, many of which offer trails or scenic spots for a break.
Yes, the New Milford River Trail Greenway is an integral part of a broader vision. It's planned to be a 13-mile town-length greenway and is part of a larger 55-mile trail connecting Gaylordsville to Norwalk, CT. Furthermore, it overlaps with the Western New England Greenway (U.S. Bike Route 7), a multi-segment, multi-state bike route linking New York City and Montreal, offering extensive touring opportunities.
Several lakes and water bodies are accessible or visible from touring cycling routes. These include Oradell Reservoir, Wild Duck Pond, Lake Tappan, and Small Water Jewel. Lake Waramaug State Park also offers a pleasant lakeside stop with picnic facilities.


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