4.9
(14)
473
riders
51
rides
Road cycling routes around Lake Mohegan offer diverse landscapes across Fairfield, Connecticut, and Westchester County, New York. The region features a mix of pristine coastline, rolling hills, and enchanting forests, providing varied terrain for cyclists. Many routes utilize mostly paved surfaces, making them suitable for road bikes. The area also includes the Long Island Sound shore, the Hudson River, and various watersheds, contributing to scenic backdrops for rides.
Last updated: May 16, 2026
7
riders
69.8km
03:44
1,070m
1,070m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
119km
06:11
1,820m
1,810m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.7
(3)
78
riders
85.0km
04:09
1,020m
1,020m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
66
riders
41.7km
01:48
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
33
riders
107km
05:51
1,860m
1,860m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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Originally a small pond, Lake Welch was increased to its current size when a dam was built in 1942. It boasts the largest beach in Harriman State Park as well as multiple picnic and bbq areas.
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Little Long Pond is beautiful any time of year, but if you happen to be riding along Kanawauke Road during the fall color season you'll be in for a real treat!
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Covering 43 acres with an average depth of 15 feet, Lake Askoti is a popular spot for fishing. The lake is stocked with hundreds of Brown Trout which means anglers have a good chance of making a catch at one of the many access points along Seve Lakes Drive.
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Lake Tiorati (Algonquin for sky-like) is one of the seven main lakes in Harriman State Park. Swimming, boating, camping, hiking, and ice-fishing are all popular activities on the lake.
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The road makes a loop around the summit of Bear Mountain with the Perkins Memorial Tower at its center. From the top you get sweeping views south across the Hudson, Harriman State Park, and the route taken by the Appalachian Trail.
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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Yorktown Heights is particularly scenic. It passes several Revolutionary War monuments and an old railway depot. The section ends at a beautiful old railway trestle bridge.
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This bronze statue is a memorial to the Battle of Pines Bridge, a battle in the Revolutionary War. The monument is made to reflect the diversity of the soldiers in the war. The monument is located in Railroad Park, which has benches and a cafe.
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As you cross over an old rail trestle bridge, you are treated to great views of the New Croton Reservoir. The bridge is not open for car traffic, so you can stop on the path for a quick break to take in the views.
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The region offers a diverse mix of landscapes. In Fairfield, Connecticut, you'll find pristine coastline, rolling hills, and enchanting forests. In Westchester County, New York, routes often feature mostly paved surfaces, traversing varied terrain including forested areas, open roads, and scenic views along the Hudson River and Long Island Sound shore.
Yes, among the 50+ road cycling routes around Lake Mohegan, there are options for various skill levels. While many routes are moderate to difficult, there are at least 2 easy routes available, providing a gentler introduction to the area's cycling opportunities.
Cyclists can enjoy several points of interest. Highlights include the impressive New Croton Dam, the historic Red Bridge over the Croton Reservoir, and the scenic The Pine Bridge Monument. You can also find stunning vistas like the View from Turkey Mountain and the expansive View of the Hudson River and the Bear Mountain Bridge from Anthony's Nose.
Absolutely. For those seeking a challenge, the area offers extensive routes. The Harriman Madness Loop is a difficult 73.8-mile (118.8 km) path, traversing varied landscapes. Another challenging option is the View of Storm King Mountain – Bear Mountain Bridge loop from Peekskill, which covers 53.1 miles (85.5 km) with significant elevation gain.
The routes around Lake Mohegan cater to a range of abilities. Out of over 50 routes, 36 are considered moderate, and 15 are difficult, featuring significant elevation changes. There are also 2 easy routes for a more relaxed experience. The region is known for its rolling hills and mountainous terrain, especially in areas like Bear Mountain.
The road cycling routes around Lake Mohegan are highly regarded by the komoot community, holding an average score of 4.9 stars from more than 10 reviews. Over 400 road cyclists have used komoot to explore the varied terrain, often praising the scenic backdrops and diverse landscapes.
Yes, many of the popular road cycling routes in the Lake Mohegan area are designed as loops. For example, the Bear Mountain Double Loop and the View from bridge – The Pine Bridge Monument loop from Shenorock are excellent circular options, allowing you to start and finish at the same point.
Lake Mohegan in Fairfield, Connecticut, is known for its 'Lake to Beach' path and surrounding areas with pristine coastline, rolling hills, and forests. Westchester County, New York, particularly near Putnam Valley, offers a robust selection of routes, often featuring mostly paved surfaces, with scenic backdrops of the Long Island Sound shore, Hudson River, and various watersheds. Both areas provide diverse terrain suitable for road cycling.
Yes, several routes in the Westchester County, New York area provide stunning views of the Hudson River. The View of Storm King Mountain – Bear Mountain Bridge loop from Peekskill, for instance, leads through scenic mountain views and along the Hudson River, offering memorable vistas.
For a significant challenge, consider the Bear Mountain Double Loop, a 43.3-mile (69.8 km) trail with substantial elevation gain through mountainous terrain. Another difficult option is the Viewpoint - Bear Mt Summit – Bear Mountain Bridge loop from Peekskill, which also features considerable climbing.
The region is rich in natural beauty. You'll encounter pristine coastlines, rolling hills, and enchanting forests, particularly in Fairfield, CT. In Westchester County, NY, routes often feature views of the Long Island Sound shore, the Hudson River, and various watersheds, providing a diverse and scenic cycling experience.


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