4.9
(7)
77
riders
12
rides
Touring cycling around Village of Brewster offers access to an extensive network of car-free paths, including segments of the Empire State Trail, Maybrook Trailway, and Putnam Trailway. The region features diverse scenery, from wetland areas and state forests to views of lakes like Whaley Lake and Tonetta Lake. While many routes utilize flat rail trail grades, the broader area also presents more challenging paths with significant elevation gains.
Last updated: July 7, 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
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 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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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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There are 13 touring cycling routes available around the Village of Brewster. These routes cater to various skill levels, with 4 easy, 7 moderate, and 2 difficult options.
Yes, the Village of Brewster offers 4 easy touring cycling routes, many of which utilize car-free paths like segments of the Empire State Trail, Maybrook Trailway, and Putnam Trailway. These trails often follow abandoned railroad rights-of-way, providing mostly flat and paved surfaces ideal for families and beginners. An example of an easy route is the Maybrook Trailway – Maybrook Trailway loop from Brewster, which is 16.2 miles (26.1 km) long.
You can expect a diverse range of terrain. Many routes utilize the gentle grades of former rail trails, offering flat and paved surfaces. However, the broader area also includes more challenging paths with significant elevation gains, such as the Senior Hill – The Pine Bridge Monument loop from Southeast, which features over 2,300 feet (700 meters) of elevation gain. You'll cycle through wetland areas, state forests, and past lakes.
Yes, several routes are designed as loops, allowing you to start and end in the same location. For example, the popular Maybrook and Putnam Trailways Loop is a 37.4 miles (60.2 km) route connecting major car-free rail trails. Another option is the moderate Whaley Lake – Maybrook Trailway loop from Brewster, which is 49.5 miles (79.7 km) long.
The routes offer diverse scenery, including views of lakes such as Whaley Lake and Tonetta Lake, wetland areas perfect for birdwatching, and extensive state forests. You'll also encounter segments along the East Branch of the Croton River. The 'Old Put' trail section, part of the Empire State Trail, is known for its continuous tree canopy and picturesque views.
Yes, the rail trails themselves are rich in history, often featuring historic markers and remnants of the old railroad lines. Within the Village of Brewster, you can find the Walter Brewster House, a notable Greek Revival style home built in 1850, adding to the historic charm of the area. The village itself features old brick buildings and picturesque Victorians.
The Village of Brewster is highly accessible via public transport. Its train station on the Metro-North Harlem Line makes it convenient for cyclists traveling with their bikes from New York City. This allows for easy point-to-point touring options.
While specific parking locations for each trailhead are not detailed here, the Village of Brewster is a key access point for major trail networks. Given its role as a hub for the Empire State Trail, Maybrook Trailway, and Putnam Trailway, parking facilities are typically available near trail access points within or close to the village.
Yes, the trails are generally equipped with benches for resting. Many tours highlight picnic areas, and the Village of Brewster itself offers opportunities to restock on snacks and water. Local establishments, such as the Bull & Barrel brewpub, provide options for post-ride refreshments and meals, adding to the community charm.
The diverse scenery and varied terrain make touring cycling enjoyable across multiple seasons. Spring and fall offer pleasant temperatures and beautiful foliage, while summer provides lush green landscapes. Given the extensive car-free paths, conditions are generally favorable outside of heavy snow or ice.
The touring cycling routes around Village of Brewster are highly rated by the komoot community, with an average score of 4.9 stars from over 40 reviews. Cyclists often praise the extensive network of car-free paths, the diverse landscapes ranging from wetlands to state forests, and the options available for different ability levels.
Many of the touring cycling routes around Village of Brewster are indeed car-free, utilizing segments of major trail networks like the Empire State Trail, Maybrook Trailway, and Putnam Trailway. These trails are often built on abandoned railroad rights-of-way, providing dedicated paths away from vehicular traffic, which is ideal for touring cyclists.


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