4.9
(22)
198
riders
11
rides
Touring cycling routes around Brewster Hill, New York, traverse a landscape characterized by extensive paved rail trails and scenic waterways. The region features multi-use paths like the Empire State Trail and Putnam Trailway, offering continuous routes through varied terrain. Cyclists encounter forested areas, wetlands, and picturesque bodies of water such as Lake Mahopac and Lake Gleneida. Elevation changes range from gentle gradients on rail trails to more significant climbs on some road sections.
Last updated: July 2, 2026
60.2km
03:41
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
25
riders
42.0km
02:27
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
21
riders
13.5km
00:52
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4.8
(5)
19
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
22
riders
48.3km
02:56
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Brewster Hill
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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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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It's along the rail trail. No fishing and no swimming from the trail side.
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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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Here you have a great view of the Middle Branch Reservoir.
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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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offers possible resting spots with shade. good for people watching as well :)
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Brewster Hill offers a diverse range of touring cycling routes, primarily featuring extensive paved rail trails like the Empire State Trail, Putnam Trailway, and Maybrook Trailway. You'll find routes suitable for various fitness levels, from easy, flat rides to more challenging options with significant elevation gains. The area has 4 easy routes, 10 moderate routes, and 2 difficult routes.
Yes, Brewster Hill has several easy touring cycling routes perfect for beginners or families. These often utilize the paved rail trails, which offer gentle gradients and a safe environment away from vehicle traffic. For example, the Maybrook Trailway – Maybrook Trailway loop from Brewster is an easy 16-mile route.
Cyclists in Brewster Hill can expect picturesque scenery including shady hardwoods, wetland areas, and stunning views of various bodies of water such as Lake Mahopac, Lake Casse, Lake Gleneida, and Whaley Lake. The routes often follow old railroad corridors, providing a unique blend of natural beauty and historical context.
Yes, several touring cycling routes in Brewster Hill are designed as loops, allowing you to start and end in the same location. Examples include the challenging Maybrook and Putnam Trailways Loop, or the moderate Whaley Lake – Maybrook Trailway loop from Brewster.
Along the routes, you can explore various points of interest. The Maybrook Trailway itself is a significant feature. You might also encounter natural sights like Titicus Reservoir North Side, or historical landmarks such as the Ninham Mountain Fire Tower. The village of Brewster also offers a charming Main Street with local shops.
Many routes are easily accessible. The village of Brewster is served by Metro-North train, and bikes are allowed on the train, making it convenient for touring cyclists traveling from and to New York City. For specific starting points, parking is often available near trailheads, especially along the major rail trails.
Yes, the charming village of Brewster, often referred to as the 'Hub of the Harlem Valley,' provides a quaint Main Street with local shops and eateries where you can refuel. Some routes may also pass through other small towns or near amenities, offering opportunities for breaks.
The best time for touring cycling in Brewster Hill is typically during the spring, summer, and fall months. Spring offers lush greenery, summer provides warm weather for lake views, and fall showcases vibrant foliage. Always check local weather conditions before heading out.
The touring cycling routes in Brewster Hill are highly rated by the komoot community, with an average score of 4.9 stars from over 40 reviews. Cyclists often praise the well-maintained rail trails, the diverse scenery encompassing lakes and forests, and the accessibility of routes for various skill levels.
Yes, experienced cyclists looking for a challenge will find routes with significant elevation gains. For instance, the Senior Hill – The Pine Bridge Monument loop from Southeast is a difficult 43-mile route with over 2,300 feet of elevation gain, offering varied terrain.
While popular rail trails can see more activity, exploring sections of the Maybrook Trailway or venturing onto some of the more challenging road routes can offer a quieter experience. Early mornings or weekdays are generally less crowded times to ride.
Touring cycling routes in Brewster Hill vary significantly in length. You can find shorter, easy rides around 16 miles, such as the Maybrook Trailway – Maybrook Trailway loop from Brewster. Longer, more challenging routes can extend up to 50 miles, like the Whaley Lake – Maybrook Trailway loop from Brewster.


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