4.5
(17)
864
riders
25
rides
Road cycling around Brewster Hill features a network of routes traversing varied terrain. The region includes established trails like the Maybrook Trailway and sections of the Empire State Trail. Cyclists can expect a mix of longer routes with notable elevation changes and shorter, more accessible paths. The landscape offers diverse settings for road cycling, from open stretches to areas near water bodies.
Last updated: May 5, 2026
119km
05:02
770m
770m
Cycle the challenging 74-mile Hudson Valley Greenway Trail Loop, featuring diverse scenery and 2516 feet of elevation gain.
45
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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19
riders
18.9km
00:45
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
28
riders
27.6km
01:14
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
9
riders
15.3km
00:41
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Brewster Hill
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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Nice little park with benches by an old little railroad station. The cafe on the south side of the park is a good place to stop as well.
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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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There are over 25 road cycling routes around Brewster Hill, offering a variety of options for different skill levels and preferences. The komoot community has explored these routes over 500 times.
Yes, Brewster Hill offers several easy road cycling routes perfect for beginners. For example, the Maybrook Trailway – Maybrook Trailway loop from Brewster is an easy 11.7-mile (18.9 km) route, and the Quiet resting spot loop from Southeast is another easy option at 9.5 miles (15.3 km).
For experienced road cyclists seeking a challenge, the Empire State Trail: Hudson Valley Loop is a difficult 74.0-mile (119.0 km) route with significant elevation changes, taking over 5 hours to complete. There are a total of 4 difficult routes in the area.
Yes, for those looking for longer rides, the Empire State Trail: Hudson Valley Loop is a substantial 74.0-mile (119.0 km) route. Another great option is the Maybrook Trailway – Whaley Lake loop from Brewster, which covers 49.5 miles (79.7 km).
Road cycling around Brewster Hill features a mix of established trails, rolling terrain, and routes that often pass near lakes. You'll find diverse settings, from open stretches to areas with more varied landscapes, including notable elevation changes on some longer routes.
Many of the road cycling routes around Brewster Hill are designed as loops. Examples include the Maybrook Trailway – Whaley Lake loop from Brewster and the Quiet resting spot loop from Brewster, offering convenient starting and ending points.
While cycling, you might encounter scenic spots like the Titicus Reservoir North Side. For panoramic views, consider visiting Mount Nimham or the Ninham Mountain Fire Tower, which are popular highlights in the wider Brewster Hill area.
The road cycling routes in Brewster Hill are highly rated by the komoot community, with an average score of 4.0 stars from over 15 reviews. Cyclists often praise the varied terrain, the network of established trails like the Maybrook Trailway, and the options available for all ability levels.
Yes, the Maybrook Trailway is a prominent feature in the region's road cycling network. Routes like the Maybrook Trailway – Whaley Lake loop from Brewster and the Maybrook Trailway – Maybrook Trailway loop from Brewster incorporate sections of this popular trail.
Many routes in Brewster Hill offer views of or pass near water bodies. The Maybrook Trailway – Whaley Lake loop from Brewster, for instance, passes by Whaley Lake, providing a scenic experience.
Route durations vary significantly based on distance and difficulty. Shorter, easy routes like the Maybrook Trailway – Maybrook Trailway loop from Brewster can be completed in under an hour, while longer, difficult routes such as the Empire State Trail: Hudson Valley Loop can take over 5 hours.


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