4.5
(4)
80
riders
23
rides
Road cycling around Maybrook, New York, is characterized by its extensive multi-use paved trails, notably the Maybrook Trailway. This region offers generally flat terrain with minimal grades, making it accessible for various skill levels. Cyclists can experience diverse landscapes, including dense woods, open farm fields, and picturesque ponds and wetlands, often alongside an active railroad line. The area's connectivity to larger regional trail systems like the Putnam County Trailway and Dutchess Rail Trail allows for continuous car-free cycling.
Last updated: July 12, 2026
42
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
7
riders
69.1km
03:05
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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6
riders
64.5km
02:51
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
41.1km
01:45
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
5
riders
41.0km
02:01
280m
280m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The windiest piece of rail trail I've ever seen
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This longer section of the Walden-Wallkill Rail Trail is completely paved and is pretty flat. Since it follows an old train line, it technically climbs slightly uphill in one direction and is completely downhill when traveling in the other direction.
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The Shawangunk Grasslands National Wildlife Refuge covers an area of 597 acres. It was initiated to support migratory birds and wintering raptors. It has great views of the stunning Shawangunk Ridge. It is a beautiful area to cycle around.
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Shawangunk Kill is a 47.2-mile-long stream that flows through several counties in New York. This point provides a nice view of the stream from a small bridge, making it an ideal spot for a quick break before you continue.
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The lake is somewhat concealed from the road, but it becomes visible from the bridge, offering a clear view of the lake and the Mara Kill branching from it. This spot is perfect for a quick view before continuing on your ride.
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In this National Historic Landmark District, there are 7 historic stone-house museums, a reconstructed church from 1717, an old burying ground and a replica Esopus Munsee wigwam. This is a great outdoor museum to explore. Keep an eye out for the blue and yellow signs, which provide information on the different buildings.
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The Huguenot Street Historic District is an outdoor musuem displaying the 300 year history of the area.
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Maybrook offers a good selection of road cycling routes, with over 20 tours available. These routes cater to various skill levels, ensuring there's something for everyone.
The road cycling routes around Maybrook are generally accessible, with 5 easy and 16 moderate tours. The prominent Maybrook Trailway is largely flat with a maximum grade of about 1.5%, making it suitable for a wide range of cyclists.
You can expect diverse and scenic landscapes. Routes often traverse dense woods, alongside farm fields, and past picturesque ponds and wetlands. The main Maybrook Trailway is a paved, multi-use path, offering a smooth ride away from traffic.
Yes, the Maybrook Trailway is a crucial link in a larger regional trail system. It connects to the Putnam County Trailway and the Dutchess Rail Trail, allowing for continuous car-free cycling for significant distances. You can even connect to the extensive Empire State Trail, with the potential to ride almost 100 miles between New York City and Kingston.
While cycling, you might encounter several natural highlights. The Maybrook Reservoir is excellent for birdwatching, and nearby Stewart State Forest offers wetlands, fields, and forests with diverse wildlife. You can also find Diamond Lake within Winding Hills County Park.
The Maybrook Trailway itself is a significant feature, running alongside the active Maybrook Line, a 'rail with trail' system. Informational signs along the route provide insights into the area's rich railroad history, offering a unique blend of nature and heritage.
While specific parking areas for the Maybrook Trailway are not detailed here, it's generally recommended to look for designated trailheads or public parking in nearby towns like Hopewell Junction, which offers access to amenities and the trail.
Yes, several routes offer a circular experience. For example, the Skydive the Ranch – View of the Shawangunk Kill loop from Town of Montgomery is a moderate 42.9-mile loop providing scenic vistas. Another option is the View of the Shawangunk Kill loop from Town of Montgomery, a 41-mile moderate route.
The Maybrook Trailway offers a remote and serene cycling experience, meaning services and restrooms are not readily available directly along its 24-mile length between Brewster and Hopewell Junction. However, connecting towns like Hopewell Junction provide access to local businesses and amenities, including a railroad depot museum.
Absolutely. The Maybrook Trailway's generally flat, paved surface and minimal grade make it an excellent choice for family-friendly cycling. Its car-free nature ensures a safe and enjoyable experience for riders of all ages.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the quiet, car-free experience on the paved trails, the diverse landscapes of woods and farm fields, and the connectivity to a broader network of trails.


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