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Routes
Road cycling routes
United States
New York
Dutchess County

Shorehaven

The best road cycling routes around Shorehaven

5.0

(12)

535

riders

38

rides

Road cycling around Shorehaven offers diverse terrain, ranging from paved rail trails to routes with significant elevation gains. The region features varied landscapes, including wetlands, forests, and views from prominent structures like the Walkway Over the Hudson. Cyclists can expect a mix of flat sections and challenging climbs, with some routes extending for many miles. This area provides opportunities for both leisurely rides and more demanding endurance challenges.

Best road cycling routes around Shorehaven

  • The most popular road cycling route…

Last updated: May 21, 2026

5.0

(8)

137

riders

#1.

Whaley Lake – Walkway Over the Hudson loop from Patterson

103km

04:17

620m

620m

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

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Moderate

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

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

Easy

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

Moderate

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Popular around Shorehaven

Hiking around Shorehaven

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Tips from the Community

LuisG
August 24, 2025, Lake view

Should be the top and relatively flat. All downhill either direction

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Air pump!! and some tools at this location.

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Excellent views

Translated by Google

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Elevator goes to the waterfront

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Alex Tray
June 16, 2025, Lake view

Pretty lake on one side and a marsh on the other

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It has tours!

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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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Alex
September 13, 2024, Walkway Over the Hudson

The Walkway Over the Hudson, also known as the Poughkeepsie Bridge, is a steel cantilever bridge spanning the Hudson River between Poughkeepsie and Highland. Originally it was built as a railroad bridge in 1889, then closed in 1974 due to fire damage and later reopened as a pedestrian walkway in 2009. It connects the Hudson Valley Rail Trail with the Dutchess Rail Trail and is part of the Empire State Trail. Stretching 6,768 feet, it was the world’s longest pedestrian footbridge until 2016. The bridge is free to access and welcomes cyclists as well as foot traffic.

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Frequently Asked Questions

How many road cycling routes are available in Shorehaven?

Shorehaven offers a wide selection of road cycling routes, with over 35 options available. These routes cater to various skill levels, from easy rides to more challenging endurance tests.

What types of terrain can I expect on road cycling routes in Shorehaven?

You'll find diverse terrain, including paved rail trails, rolling hills, and routes with significant elevation gains. The region features varied landscapes, from wetlands along trails like the Maybrook Trailway to scenic views from structures like the Walkway Over the Hudson.

Are there easy road cycling routes suitable for beginners in Shorehaven?

Yes, Shorehaven has several easy road cycling routes perfect for beginners. One accessible option is the Gas station to refill water loop from Route 55 & Route 216 (CR 32), an 18.9-mile path with moderate elevation changes.

Are there challenging road cycling routes for experienced cyclists in Shorehaven?

Absolutely. For experienced cyclists seeking a challenge, routes like the Whaley Lake – Walkway Over the Hudson loop from Patterson offer significant elevation gains over 64.1 miles, often taking over 4 hours to complete. This route includes substantial climbs and passes by the historic Walkway Over the Hudson.

What are some popular road cycling loops in Shorehaven?

Beyond the challenging Whaley Lake loop, local road cyclists also enjoy the Seeley Hill – Bulls Bridge loop from Pawling, a 40.3-mile trail with notable climbs. Another popular option is the Whaley Lake – Whaley Lake loop from Patterson, which covers 49.3 miles with considerable elevation.

What scenic viewpoints or landmarks can I see along road cycling routes in Shorehaven?

Many routes offer scenic views. You can cycle across the historic Walkway Over the Hudson, which was once the world's longest pedestrian footbridge. The Maybrook Trailway traverses wetlands, and you might encounter views from Mount Nimham. Additionally, the Whaley Lake area provides picturesque settings.

Are there opportunities for birdwatching while cycling in Shorehaven?

Yes, several trails in Shorehaven are excellent for birdwatching. The Maybrook Trailway, for instance, traverses wetlands known for diverse birdlife. In the South Haven, Michigan area, the Kal-Haven Trail also runs through varied landscapes, including beech-maple forests, which are ideal for birdwatching.

What is the best season for road biking in Shorehaven?

While specific conditions vary, spring through fall generally offer the most pleasant weather for road cycling in Shorehaven, allowing you to enjoy the diverse landscapes and scenic views. Always check local weather forecasts before heading out.

Are there any unique rail trails to explore in Shorehaven?

Shorehaven is home to notable rail trails. The Maybrook Trailway is a paved path spanning over 28 miles, connecting to other major trails like the Hudson Valley Rail Trail and the Dutchess Rail Trail. In the South Haven, Michigan area, the Kal-Haven Trail offers a well-groomed, 34-mile path, primarily crushed limestone, with historical panels and amenities.

Are there any trails with amenities like water stops or restrooms?

Yes, particularly on longer rail trails. The Kal-Haven Trail in the South Haven, Michigan area, for example, is known for offering facilities such as water pumps, bathrooms, picnic areas, and bike fix-it stations along its route.

What do other road cyclists enjoy most about road cycling in Shorehaven?

The road cycling routes in Shorehaven are highly rated by the komoot community, with an average score of 4.0 stars from over 10 reviews. Cyclists often praise the diverse terrain, from extensive rail trails to challenging climbs, and the scenic views, including those from the Walkway Over the Hudson.

Can I combine road cycling with other activities in Shorehaven?

Absolutely. In the South Haven, Michigan area, you can combine cycling with exploring high dune formations and sandy beaches along Lake Michigan. The region also features the Lake Michigan Shore Wine Trail, offering opportunities to visit local wineries. The New York region provides access to various natural attractions and historical sites.

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