4.8
(9)
440
riders
28
rides
Road cycling around Brewster Heights offers diverse terrain, characterized by a mix of paved rail-trails, scenic lakes, and wooded areas. The region features routes that traverse former railroad corridors, providing relatively flat sections alongside areas with moderate elevation changes. Natural features such as Lake Mahopac, Lake Casse, and the Middle Branch Reservoir contribute to the picturesque landscapes encountered on many routes.
Last updated: July 12, 2026
119km
05:02
770m
770m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
75
riders
42.0km
01:42
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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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.
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 Brewster Heights
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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There are over 25 road cycling routes around Brewster Heights, catering to various skill levels. You'll find a good mix, with 5 easy routes, 14 moderate routes, and 6 more challenging options.
Road cycling around Brewster Heights offers diverse terrain. You'll encounter a mix of paved rail-trails, which provide relatively flat sections, alongside areas with moderate elevation changes. The region features picturesque landscapes with scenic lakes and wooded areas, offering both gentle rides and satisfying climbs.
Yes, for those seeking longer rides, the area offers extensive options. A notable route is the Empire State Trail: Hudson Valley Loop, which is a challenging 74-mile (119 km) route. Additionally, the Putnam Trailway, a 45-mile paved corridor, provides a long, scenic ride through the region.
The routes in Brewster Heights are rich with natural beauty. You can expect to see several beautiful bodies of water, including Lake Mahopac, Lake Casse, Lake Gleneida, and the Middle Branch Reservoir. The Maybrook Trailway itself offers varied scenery, and you might also encounter views from Mount Nimham or the Ninham Mountain Fire Tower.
Yes, there are several loop options. A popular choice is the Maybrook Trailway – Whaley Lake loop from Brewster, a moderate 49.5-mile (79.7 km) path that follows the Maybrook Trailway and passes by Whaley Lake. Another option is the shorter Quiet resting spot loop from Brewster.
The area is highly rated by the komoot community, with an average score of 4.8 stars from 9 reviews. Cyclists often praise the varied terrain, which includes both flat rail-trails and routes with significant elevation gain, as well as the scenic beauty of the lakes and wooded sections.
Yes, the paved rail-trails, such as sections of the Putnam Trailway, are generally suitable for families due to their relatively flat and well-maintained surfaces. These trails offer a safe and scenic environment for cyclists of all ages.
The region's picturesque landscapes, with shady hardwoods and beautiful bodies of water, are particularly enjoyable during spring, summer, and fall. Spring offers fresh greenery, summer provides lush scenery, and autumn brings vibrant foliage, making these seasons ideal for road cycling.
Beyond the scenic routes themselves, you can find several points of interest. The Maybrook Trailway is a highlight in itself. You can also find the Titicus Reservoir North Side, and for those interested in views, Mount Nimham and the Ninham Mountain Fire Tower offer elevated perspectives.
The Putnam Trailway, a significant cycling corridor, begins in Brewster at Putnam Avenue. This suggests good accessibility for those arriving by public transport, such as Metro-North, which often allows bikes with a permit. It's advisable to check specific train line policies for bike carriage.
While popular routes like the Putnam Trailway can see more activity, exploring some of the less-trafficked local roads or the quieter sections of the Maybrook Trailway, such as the Maybrook Trailway – Whaley Lake loop from Croton Falls, might offer a more serene experience. The region's extensive network provides opportunities to find quieter paths, especially during off-peak hours.


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