4.8
(9)
403
riders
28
rides
Road cycling routes around Village of Brewster traverse a landscape characterized by extensive paved pathways, river valleys, and historic rail trails. The region offers a strategic connection to significant trail networks, including the Empire State Trail and the Maybrook Trailway. Cyclists can expect varied terrain, from flat, scenic sections along waterways like the East Branch of the Croton River to routes with considerable elevation gain through woodlands and past historic sites. This area provides a blend of natural beauty and…
Last updated: July 7, 2026
119km
05:02
770m
770m
Cycle the challenging 74-mile Hudson Valley Greenway Trail Loop, featuring diverse scenery and 2516 feet of elevation gain.
5.0
(2)
80
riders
80.7km
03:28
700m
690m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
71
riders
42.0km
01:42
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
27
riders
33.5km
01:27
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
50
riders
57.2km
02:28
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Village of Brewster
This paved rail trail traverses two counties in New York — you can bike more than 28 miles on it if you go from end to end. This particular section passes through a sort of wetland land — keep an eye out for birds!
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Lots of benches just off the paved trail to rest your legs or to enjoy the scenery.
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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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Lake Casse is a 30-acre lake that is owned and managed by the Lake Casse Park District. There is a beach, public restrooms, a playground, and a clubhouse.
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Great views of Croton reservoir and the red bridge itself is worth a stop. That said watch out for stopped cyclist and pedestrians if you're biking through.
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The Village of Brewster offers a diverse selection of over 25 road cycling routes. These routes cater to various skill levels, with options ranging from easy to difficult, ensuring there's something for every cyclist.
Road cycling routes in the Village of Brewster feature a mix of terrain. You'll find extensive paved pathways, including sections of the Empire State Trail and the Maybrook Trailway, offering relatively flat and scenic rides. Other routes may include significant elevation gain as they traverse through woodlands and past historic sites, providing a more challenging experience.
While cycling, you can enjoy scenic views along the East Branch of the Croton River and pass by the historic Tudor train station. The area also features green spaces like the Brewster Preserve and the Diverting Reservoir. The Maybrook Trailway – Whaley Lake loop from Brewster, for example, offers picturesque views around Whaley Lake.
Yes, the Village of Brewster is rich in history. You can cycle past charming Victorian and old Colonial homes, and the historic Walter Brewster House (built in 1850) is a notable landmark. The area also has a strong railroad history, with the Metro-North Harlem Line still serving the village. The Tilly Foster Mine, once the world's deepest open-pit mine, is also nearby.
Yes, the Village of Brewster offers several moderate routes that are great for beginners and families. These often utilize the paved rail trails like sections of the Putnam Trailway. For example, the Quiet resting spot loop from Brewster is a moderate route leading through varied local landscapes.
Absolutely. For advanced cyclists seeking a challenge, routes like the Empire State Trail: Hudson Valley Loop offer significant elevation gain and a longer distance, providing a strenuous and rewarding ride with diverse scenery.
The spring, summer, and fall months are ideal for road cycling in the Village of Brewster. Fall is particularly scenic, with vibrant foliage along the routes. The well-maintained paved trails make cycling enjoyable across these seasons.
Parking is generally available at various trailheads for the Maybrook Trailway and Putnam Trailway in and around Brewster. Specific parking information for trailheads can often be found on local government websites or trail-specific resources. For more information on the Empire State Trail section through Brewster, you can visit ny.gov.
Yes, the Village of Brewster is served by the Metro-North Harlem Line, making it accessible by public transport. This allows cyclists to reach the village and connect to the extensive network of trails, including the Empire State Trail, which runs directly through the village.
While the paved rail trails like the Maybrook Trailway and Putnam Trailway are generally popular for walking and cycling, it's important to check specific trail regulations regarding dogs, especially when cycling. Many trails allow leashed dogs, but always confirm local rules before heading out.
The Village of Brewster itself offers various cafes, pubs, and restaurants where you can stop for refreshments. Many routes, especially those passing through or near the village center, provide convenient access to these amenities. The Maybrook Trailway, for instance, connects to areas where such stops are available.
The road cycling routes in the Village of Brewster are highly rated by the komoot community, with an average score of 4.8 stars from over 9 reviews. Cyclists often praise the diverse scenery, well-maintained paved trails, and the connection to major networks like the Empire State Trail.
Yes, there are several excellent circular road cycling routes that start and end in Brewster. A popular option is the Maybrook Trailway – Maybrook Trailway loop from Town Open Space (Ridgebury Road), which offers a moderate ride through the local landscape.


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