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Westchester

The best road cycling routes around Westchester

5.0

(3)

675

riders

17

rides

Road cycling around Westchester is characterized by diverse landscapes, including scenic reservoirs, views of the Hudson River, and extensive parklands. The region features a mix of rolling hills and dedicated multi-use trailways. This varied terrain provides options for different cycling preferences, from challenging climbs to leisurely rides.

Best road cycling routes around Westchester

  • The most popular road cycling route is Miami Marine Stadium – William M. Powell Bridge loop from University, a 23.7 miles (38.1 km) trail that takes…

Last updated: July 13, 2026

5.0

(3)

415

riders

#1.

Hobie Beach (Windsurfer Beach) – William M. Powell Bridge loop from Douglas Road

32.0km

01:17

30m

30m

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

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Easy

This road cycling loop offers a delightful journey through Miami's urban green spaces and the charming Coral Gables Waterway. You'll pedal past elegant Mediterranean Revival architecture and lush waterfronts, creating…

Easy
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This road cycling loop from Dadeland South offers a picturesque journey through South Florida's lush landscapes, highlighted by the magnificent, sprawling banyan trees that create a shaded canopy along the…

Moderate

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 Westchester

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Tips from the Community

Jorge
October 20, 2025, Southwest 42nd Road Pedestrian and Bicycle Bridge

Great scenic trail

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Hobie Beach, also known as Windsurfer Beach, is a fun stop if you’re riding along the Rickenbacker Causeway. It’s a popular spot for windsurfers and also one of Miami’s favorite dog-friendly beaches. The shallow water makes it safe for dogs to splash around, and there’s always something to watch—from kite sails to people enjoying the breeze.

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Nice view of the Coral Gables Waterway from the Commodore Trail. The trail is popular with cyclists, walkers, and runners, so if you want to stop to admire the view, make sure you are out of the way of other trail users.

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Nice pedestrian bridge on the Commodore Trail. It takes you over Coral Gables Waterway. The bridge is only open to cyclists and pedestrians.

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mtm05005
May 23, 2025, Regatta Park

Regatta Park, located on the shores of Biscayne Bay, is named after the sailing regattas frequently visible from its coastline. It features a boat launch and a few short paths suitable for various activities.

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These two giant banyan trees are more than 70 years old. To make sure that they are protected, they have been declared historic.

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very generously dimensioned bicycle and pedestrian bridge

Translated by Google

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Frequently Asked Questions

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

Westchester offers a diverse landscape for road cycling, characterized by scenic reservoirs, views of the Hudson River, and extensive parklands. You'll find a mix of rolling hills and dedicated multi-use trailways, providing options from leisurely rides to more challenging sections. The region's routes generally feature manageable elevation changes, with many easy routes having less than 50 meters of ascent.

Are there routes suitable for beginners or those looking for an easy ride?

Yes, Westchester has numerous easy road cycling routes. For instance, the Miami Marine Stadium – William M. Powell Bridge loop from University is an easy 23.7-mile (38.1 km) trail with minimal elevation gain, offering a pleasant ride around the stadium and bridge. Another accessible option is the View of Coral Gables Waterway – Regatta Park loop from Dadeland North, an easy 19.5-mile (31.5 km) path with scenic views.

Which routes offer scenic views or pass by notable landmarks?

Many routes in Westchester are known for their scenic beauty. The View of Coral Gables Waterway – Regatta Park loop from Dadeland North provides scenic views of the Coral Gables Waterway and passes by Regatta Park. The Old Cutler Trail – Historic Giant Banyan Trees loop from Douglas Road takes you through the Old Cutler Trail and past the impressive Banyan Trees on Old Cutler Road. The region's reservoirs, like the New Croton and Kensico, also offer picturesque backdrops for cycling.

Are there any long-distance or more challenging road cycling routes?

For those seeking a longer ride, the Old Cutler Trail – Historic Giant Banyan Trees loop from Dadeland South is a moderate 65-mile (104.5 km) route. While Westchester's routes are generally not categorized as 'difficult' in terms of extreme elevation, the longer moderate routes provide a good endurance challenge. The region's rolling hills also add variety to your ride.

What is the best time of year to go road cycling in Westchester?

The spring, summer, and fall months are ideal for road cycling in Westchester. Spring offers pleasant temperatures and blooming scenery, while summer provides warm weather for longer rides. Fall is particularly popular for its stunning foliage, especially along routes near reservoirs and parkways. Winter cycling is possible but requires checking conditions for ice and snow, as some multi-use trails may not be regularly cleared.

Are there any dedicated multi-use trailways for road cycling in Westchester?

Yes, Westchester boasts several excellent paved multi-use trailways perfect for road cycling. These include the 11.2-mile Bronx River Pathway, the 22.1-mile North County Trailway, and the 14.1-mile South County Trailway. These trailways offer traffic-free or low-traffic environments, making them great for all skill levels. The Old Croton Aqueduct State Historic Trail also provides a unique, historic cycling experience.

What do other cyclists say about road cycling in Westchester?

The road cycling routes in Westchester are highly regarded by the komoot community, with an average rating of 5.0 stars from 6 reviews. Cyclists often praise the region's diverse landscapes, scenic reservoir views, and the availability of dedicated multi-use trailways that cater to various preferences and skill levels.

Are there any family-friendly road cycling options in Westchester?

Absolutely. The dedicated multi-use trailways like the Bronx River Pathway, North County Trailway, and South County Trailway are excellent for family-friendly road cycling due to their paved surfaces and separation from vehicle traffic. These trails offer a safe and enjoyable environment for cyclists of all ages. Additionally, 'Bicycle Sundays' on the Bronx River Parkway provide a unique traffic-free experience on select dates.

Where can I find information about parking or public transport access to trailheads?

Many of Westchester's trailways and popular cycling routes offer designated parking areas at various access points. For detailed information on parking facilities and public transport options to specific trailheads, it's best to consult local park websites or resources like Westchester County Parks. Some routes, particularly those along multi-use trailways, may also be accessible via Metro-North train stations.

Are there any circular road cycling routes available?

Yes, many of the popular road cycling routes in Westchester are designed as loops, offering a convenient way to start and end your ride at the same point. Examples include the Miami Marine Stadium – William M. Powell Bridge loop from University, the View of Coral Gables Waterway – Regatta Park loop from Dadeland North, and the Old Cutler Trail – View of Coral Gables Waterway loop from Douglas Road. The New Croton Reservoir and Kensico Reservoir also feature well-known circular routes.

What are the typical lengths of road cycling routes in Westchester?

Road cycling routes in Westchester vary in length, catering to different preferences. You can find shorter, easy paths around 19-24 miles (30-39 km), such as the Miami Marine Stadium – William M. Powell Bridge loop from University. Longer routes, like the Old Cutler Trail – Historic Giant Banyan Trees loop from Dadeland South, can extend to about 65 miles (104.5 km), offering more extensive exploration of the region.

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