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Cycling routes
United States
Connecticut
Western Connecticut Planning Region

Ridgebury

The best cycling routes around Ridgebury

4.9

(7)

117

riders

22

rides

Touring cycling routes around Ridgebury primarily utilize established trailways and paths that often connect scenic lakes and local hills. The landscape features a mix of wooded sections and open areas, providing varied scenery for cyclists. Elevations are generally moderate, with some routes incorporating gentle climbs around features like Senior Hill. The region offers a network of paths suitable for different cycling preferences.

Best touring cycling routes around Ridgebury

  • The most popular touring cycling route is Maybrook and Putnam Trailways Loop

Last updated: July 9, 2026

#1.

Maybrook and Putnam Trailways Loop

60.2km

03:41

550m

550m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

5.0

(1)

25

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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5.0

(1)

21

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Ridgebury

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Tips from the Community

Ed Mal
August 10, 2025, Stewart's Farm

Coffee an Peach ride

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0

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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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.

0

0

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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0

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.

1

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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

1

0

Peter B
September 25, 2021, Maybrook Trailway

offers possible resting spots with shade. good for people watching as well :)

0

0

Frequently Asked Questions

How many touring cycling routes are available in Ridgebury?

There are over 25 touring cycling routes around Ridgebury, offering a diverse range of experiences. These routes are highly rated by the komoot community, with an average score of 4.9 stars from over 40 reviews.

Are there any easy touring cycling routes suitable for beginners in Ridgebury?

Yes, Ridgebury offers several easy routes perfect for beginners. One excellent option is the Maybrook Trailway – Maybrook Trailway loop from Brewster, which is 16.2 miles (26.1 km) long and features minimal elevation gain, making it a comfortable ride for those new to touring cycling.

What are some good options for long-distance touring cycling in Ridgebury?

For longer rides, the region provides routes that combine established trailways. The Maybrook and Putnam Trailways Loop is a challenging 37.4 miles (60.2 km) route that offers a consistent surface for extended cycling. Another great choice is the Whaley Lake – Maybrook Trailway loop from Brewster, a moderate 49.5 miles (79.7 km) path with scenic lake views.

Are there any circular touring cycling routes in Ridgebury?

Many of Ridgebury's touring cycling routes are designed as loops, allowing you to start and end in the same location. Examples include the Lake Casse – Senior Hill loop from Brewster, which is 21.8 miles (35.0 km) and incorporates a gentle climb, and the Whaley Lake – Whaley Lake loop from Brewster, a moderate 26.1 miles (42.0 km) ride.

What kind of scenery can I expect on Ridgebury's touring cycling routes?

Ridgebury's routes offer a varied landscape, featuring a mix of wooded sections and open areas. You'll often find paths connecting scenic lakes like Whaley Lake and Lake Casse, as well as gentle climbs around local hills such as Senior Hill. The region's established trailways provide consistent surfaces through these diverse environments.

What are some interesting places to explore or landmarks to see near the cycling routes?

While cycling, you can explore several notable attractions. The Maybrook Trailway itself is a significant feature. You might also encounter natural beauty spots like Sal J. Prezioso Mountain Lakes Park, Parks Pond and Picnic Site, or the Titicus Reservoir North Side. For a historical touch, Hearthstone Castle is also nearby.

When is the best time of year to go touring cycling in Ridgebury?

The best time for touring cycling in Ridgebury is typically during the spring, summer, and fall months. These seasons offer pleasant temperatures and vibrant scenery, from blooming foliage to autumn colors. The established trailways are generally well-maintained, making them accessible during these periods.

Are there any advanced or difficult touring cycling routes in Ridgebury?

Yes, for experienced touring cyclists seeking a challenge, Ridgebury offers routes with more significant distances and elevation changes. The Maybrook and Putnam Trailways Loop is classified as difficult, covering over 37 miles with notable ascents, providing a rewarding experience for advanced riders.

What do other touring cyclists say about the routes in Ridgebury?

The touring cycling routes in Ridgebury are highly regarded by the komoot community, holding an impressive average rating of 4.9 out of 5 stars from over 40 reviews. Cyclists often praise the well-maintained trailways, the scenic lake views, and the diverse terrain that caters to various skill levels.

Is parking available near the touring cycling routes in Ridgebury?

While specific parking details vary by trailhead, many established trailways and popular cycling starting points in the Ridgebury area typically offer designated parking facilities. It's advisable to check local resources or route descriptions for the most convenient parking options for your chosen tour.

Can I find cafes or places to stop for refreshments along the touring cycling routes?

Many touring cycling routes in Ridgebury utilize established trailways that often pass through or near towns and villages. While not every route will have direct access to cafes, you can generally find opportunities for refreshments in the communities adjacent to the trail network. Planning your route in advance can help identify suitable stops.

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