4.8
(39)
192
riders
14
rides
Touring cycling routes around Brewster Heights offer access to a diverse landscape in New York. The region features picturesque natural beauty, including several lakes and forested areas, with the Putnam Trailway passing by scenic bodies of water like Lake Mahopac and the Middle Branch Reservoir. Cyclists can experience miles of shady hardwood forests and varied terrain, including some challenging climbs, along historic rail corridors. This area provides a blend of natural environments and dedicated trails suitable for touring cyclists.
Last updated: May 13, 2026
60.2km
03:41
550m
550m
Cycle the Maybrook and Putnam Trailways Loop, a challenging 37.4-mile route with 1820 feet of elevation gain through scenic woodlands and pa
25
riders
26.1km
01:31
130m
120m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
5.0
(1)
27
riders
42.0km
02:27
210m
210m
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.
5.0
(1)
6
riders
19.1km
01:11
110m
110m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
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!
0
0
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.
0
0
It's along the rail trail. No fishing and no swimming from the trail side.
0
0
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
0
0
Here you have a great view of the Middle Branch Reservoir.
1
0
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
1
0
offers possible resting spots with shade. good for people watching as well :)
0
0
There are over 15 touring cycling routes around Brewster Heights, offering a diverse range of experiences. These routes are highly rated by the komoot community, with an average score of 5.0 stars from 40 reviews.
The region around Brewster Heights features picturesque natural beauty, including several lakes and forested areas. You can expect miles of shady hardwood forests and varied terrain, with some routes like the Putnam Trailway presenting satisfying challenges with steep climbs. Many routes follow historic rail corridors, offering a mix of paved and well-maintained surfaces.
Yes, Brewster Heights offers several easy touring cycling routes. For example, the Maybrook Trailway – Maybrook Trailway loop from Brewster is an easy 26 km path with minimal elevation gain, perfect for a relaxed ride.
Absolutely. For experienced riders seeking a challenge, routes like the Maybrook and Putnam Trailways Loop offer a difficult 60 km journey combining two significant trailways with substantial elevation changes. Another demanding option is the Senior Hill – The Pine Bridge Monument loop from Southeast, a 69.6 km trail with significant elevation gain.
Many routes pass by scenic bodies of water such as Lake Mahopac, Lake Casse, and the Middle Branch Reservoir. The Maybrook Trailway itself offers beautiful views. You can also find viewpoints like Mount Nimham, which provides expansive vistas of the surrounding landscape.
Beyond the natural beauty, you can explore the Ninham Mountain Fire Tower for historical interest and panoramic views. The Titicus Reservoir North Side is another notable spot for its serene waterscapes. Green Chimneys Farm & Wildlife Center, located just 15 minutes from downtown Brewster, offers a unique outdoor educational experience with over 300 animals.
Yes, many touring cycling routes in Brewster Heights are designed as loops. Examples include the popular Whaley Lake – Maybrook Trailway loop from Brewster and the Lake Casse – Senior Hill loop from Brewster, allowing you to start and end at the same point.
While specific 'family-friendly' designations vary, many of the easier, flatter sections of the rail trails, such as parts of the Putnam Trailway, are suitable for families. These trails often offer a smoother, more predictable surface away from vehicle traffic, making them enjoyable for all ages.
Many multi-use trails in the region, including sections of the Putnam Trailway and Maybrook Trailway, generally allow leashed dogs. However, it's always best to check specific trail regulations or local signage before heading out, as policies can vary.
Spring and fall generally offer the most pleasant cycling conditions with mild temperatures and beautiful foliage. Summer can also be enjoyable, especially on routes that pass through shady hardwood forests. Winter cycling is possible but requires appropriate gear and awareness of potential snow and ice conditions.
Parking is typically available at various access points along major trailways like the Putnam Trailway and Maybrook Trailway. Specific parking areas can often be found near trailheads in towns like Brewster. It's advisable to check local municipality websites or trail maps for designated parking locations.
Yes, the towns and villages along the major cycling routes, including Brewster itself, offer various cafes, restaurants, and shops where you can refuel and refresh. Planning your route to pass through these areas can enhance your cycling experience.
Brewster is served by Metro-North Railroad, making it accessible via public transport from New York City and other points. Cyclists can often bring their bikes on trains, providing a convenient way to reach the starting points of many routes, including the Putnam Trailway which begins in Brewster.


Browse the best Cycling routes in other regions.