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Road cycling routes
United States
New York
Westchester County

Rye Brook

The best road cycling routes around Rye Brook

4.4

(39)

1,764

riders

169

rides

Road cycling routes around Rye Brook feature diverse parks, green spaces, and well-maintained infrastructure. The area includes scenic routes around reservoirs and along dedicated trailways. Riders can explore varied landscapes, from expansive lawns and wooded areas to views of the Long Island Sound. The terrain generally offers a mix of flat sections and gentle inclines suitable for road cycling.

Best road cycling routes around Rye Brook

  • The most popular road cycling route is Red Mill at Kirby Tidal Pond – Playland Lake loop from Rye, a 10.9 miles (17.6 km) trail that takes 1 hour to complete. This easy route offers views of Playland Lake.
  • Another top favourite among local road cyclists is Bruce Park – Bruce Park Drive - Quiet Road loop from Port Chester, an easy 23.0 miles (37.0 km) path. This route incorporates Bruce Park and quiet roads.
  • Local road cyclists also love the Milbank Conservation Easement – Round Hill Community Church loop from Port Chester, a 39.2 miles (63.1 km) trail leading through varied terrain, often completed in about 3 hours.
  • Road cycling around Rye Brook is defined by diverse parks, reservoirs, and dedicated trailways. The network offers options for various ability levels.
  • The routes in Rye Brook are highly rated by the komoot community with an average score of 4.1 stars from over 19 reviews. More than 1200 road cyclists have used komoot to explore Rye Brook's varied terrain.

Last updated: June 26, 2026

8

riders

#1.

Stone Hill Road loop from Byram River Gorge

58.0km

02:42

690m

690m

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

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Moderate

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

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

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

Moderate
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Popular around Rye Brook

Hiking around Rye Brook

Cycling around Rye Brook

Running Trails around Rye Brook

Tips from the Community

Felix
August 10, 2025, Byram Lake Reservoir

This is a beautiful reservoir on a road which is gravel for about 2 miles and asphalt otherwise. Along the reservoir there is a grassy very small park with two benches which is a nice place to stop.

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The park is situated in a small valley that offers a steady climb up the road no matter which direction you choose.

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Zachary
January 24, 2025, Streets Pond

Streets Pond is a long, thin, and stretches under the road as you ride by. There are wooden fences that make it difficult to get a good view from the road, but if you pull up on the sidewalk you can look down the length of the forested pond.

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Scott
February 29, 2024, Pear Tree Point Cove

Pear Tree Point Cove is a sheltered inlet off Long Island Sound, providing a calm environment for various marine life. The diverse birdlife in and around the cove attracts birdwatchers, offering opportunities to observe various species throughout the year. The cove offers stunning water views and is surrounded by lush greenery, making it a picturesque location for relaxation.

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Natalie
February 25, 2024, Crawford Park

The road through Crawford Park runs east to west, past the historic mansion and through the beautiful park. It's a popular place to be outdoors with plenty of people joining you in exercise through hiking, running and cycling.

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Alex
February 1, 2024, Taconic Road

The views from this fast flowing and good quality road are lovely. With trees and quiet fields around you will gain a feeling of inner peace cycling along it.

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Alex
January 31, 2024, Stone Hill Road

Stone Hill Road is a cracking road to cycle on with good quality tarmac and plenty of wildlife to keep your eye out for.

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Jamie S.
January 17, 2024, Twin Lakes

The Twin Lakes in Bedford, New York straddle either side of Twin Lakes Drive, making for a scenic section of riding. Keep an eye out for turtle crossings in the spring and summer!

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Frequently Asked Questions

How many road cycling routes are available around Rye Brook?

Rye Brook offers a wide selection of road cycling routes. There are over 160 routes available, catering to various skill levels and preferences.

What kind of terrain can I expect on road cycling routes around Rye Brook?

The region features a diverse landscape, from expansive lawns and wooded areas to scenic views of the Long Island Sound. You'll find a mix of well-paved surfaces, with routes offering both flat sections and gentle inclines. Some segments, particularly on trailways, might have varied surface conditions.

Are there easy road cycling routes suitable for beginners in Rye Brook?

Yes, Rye Brook has numerous easy road cycling routes perfect for beginners. For example, the Kensico Reservoir loop from Byram River Gorge is an easy 22.2 km ride offering scenic views. Another great option is the Crawford Park – Crawford Park loop from Rye, an easy 29.3 km path through a beautiful park.

What are some scenic road cycling routes with good views in the area?

For scenic rides, consider routes around the Kensico Reservoir, which offers beautiful water views. Rye Town Park and Rye Hills Park also provide scenic views of the Long Island Sound. The Byram Lake Reservoir – View of Rockwood Lake loop from Rye is another moderate option known for its picturesque landscapes.

Can I find longer, more challenging road cycling routes near Rye Brook?

Absolutely. For those seeking a longer and more challenging ride, the South County Trailway – Putnam Trail loop from Rye is a moderate 69.9 km route. Another option is the Binney Park – East Coast Greenway loop from Byram River Gorge, a moderate 67.1 km ride with significant elevation gain.

Are there any dedicated cycling trails or trailways in the Rye Brook area?

Yes, the region benefits from dedicated cycling infrastructure. The South County Trailway is a significant asphalted route that extends from New York City, offering a good cycling experience. Many routes incorporate sections of these trailways.

What natural features or landmarks can I see along the road cycling routes?

Road cycling routes in Rye Brook often pass through diverse parks and natural preserves. You can explore Binney Park, Crawford Park with its expansive lawns, and the scenic Kensico Reservoir. Nearby nature preserves like Marshlands Conservancy and Edith G. Read Wildlife Sanctuary also offer opportunities to enjoy nature and birdwatching, complementing your ride.

Is Rye Brook a good destination for family-friendly road cycling?

Yes, Rye Brook is suitable for family-friendly road cycling, especially with its easy routes and parks. The Crawford Park loop from Rye is an easy ride that incorporates a 35-acre park with open spaces, making it a pleasant option for families.

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

The spring and summer months, particularly May and June, are popular for cycling in Rye Brook due to favorable weather conditions. The diverse parks and green spaces are especially vibrant during these seasons, enhancing the riding experience.

Where can I find parking for road cycling routes in Rye Brook?

Many parks and trailheads in and around Rye Brook offer parking facilities. For instance, parks like Crawford Park and Rye Town Park provide accessible parking. For routes utilizing the South County Trailway, look for designated parking areas along its length.

Is public transport available to access road cycling trails in Rye Brook?

While specific public transport connections directly to trailheads may vary, Rye Brook is part of the broader Westchester County public transport network. It's advisable to check local bus schedules or Metro-North train lines for stations near your desired starting points, keeping in mind bike carriage policies.

Are there any permits required for cycling on trails in Rye Brook?

Generally, permits are not required for cycling on public roads and designated multi-use trails like the South County Trailway in Rye Brook. However, always check specific park regulations if you plan to cycle within certain managed park areas, as rules can vary.

What do other cyclists say about road cycling in Rye Brook?

The road cycling routes around Rye Brook are highly rated by the komoot community, with an average score of 4.1 stars from over 26 reviews. Cyclists often praise the diverse parks, scenic reservoirs, and well-maintained trailways that make for an enjoyable riding experience.

Are there places to stop for refreshments like cafes along the routes?

Rye Brook and its surrounding towns offer various amenities. While specific cafes directly on every route might be limited, you'll find options in the nearby town centers and villages. Planning your route to pass through these areas will allow for refreshment stops.

Most popular routes around Rye Brook

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