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Routes
Road cycling routes
United States
New York
Putnam County

Brewster Hill

The best road cycling routes around Brewster Hill

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.

Best road cycling routes around Brewster Hill

  • The most popular road cycling route is Empire State Trail: Hudson…

Last updated: May 5, 2026

#1.

Empire State Trail: Hudson Valley Loop

119km

05:02

770m

770m

Cycle the challenging 74-mile Hudson Valley Greenway Trail Loop, featuring diverse scenery and 2516 feet of elevation gain.

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Hard

45

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Popular around Brewster Hill

Hiking around Brewster Hill

Cycling around Brewster Hill

Running Trails around Brewster Hill

Tips from the Community

Lisa
June 23, 2025, Trailside Café

A great place to stop for a snack and a quick drink.

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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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AverieOutside
January 25, 2024, Lake Casse

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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An American Revolution Monument

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Buck R-T
July 10, 2022, Whaley Lake

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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Frequently Asked Questions

How many road cycling routes are available in the Brewster Hill area?

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.

Are there any easy road cycling routes suitable for beginners in Brewster Hill?

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).

What are some challenging road cycling routes for experienced riders around Brewster Hill?

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.

Are there any long-distance road cycling routes in Brewster Hill?

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).

What kind of terrain can I expect on road cycling routes in Brewster Hill?

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.

Are there any circular road cycling routes in the area?

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.

What are some scenic viewpoints or attractions I can see along the road cycling routes?

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.

What do other road cyclists enjoy most about road cycling in Brewster Hill?

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.

Are there routes that utilize the Maybrook Trailway?

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.

Can I find routes that pass by lakes or water bodies?

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.

What is the typical duration for a road cycling route in Brewster Hill?

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.

Most popular routes around Brewster Hill

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