4.2
(35)
1,373
riders
18
rides
Road cycling around Port Chester offers diverse terrain across Westchester County and into Connecticut, providing varied landscapes for cyclists. The region features a mix of flat sections and challenging routes with significant elevation gains, catering to different fitness levels. Natural features include several reservoirs like Byram Lake Reservoir and Titicus Reservoir, which provide scenic backdrops. The area's geography allows for rides through both coastal areas and more hilly inland sections.
Last updated: April 28, 2026
24
riders
63.4km
03:04
570m
570m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
58.0km
02:43
620m
620m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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4.6
(5)
40
riders
27.9km
01:11
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
14
riders
118km
05:16
1,210m
1,210m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
26
riders
69.3km
03:23
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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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Great stretch of a well paved and quiet road. There is little to no shoulder though, so that might put off les experienced riders.
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A wide crushed stone path takes you along the coast of the park. A short jetty juts out from a grassy area with picnic tables and a view out across the water. You can see the New York City skyline clearly on a good day.
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This late Gothic Revival-style chapel is on the National Register of Historic Places; it's run by a volunteer board of trustees and is available for both religious and secular activities.
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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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As you pass over Cross River Bridge, you get a great view of the water below. The traffic is normally light, so you should be able to go slowly to enjoy the view. There is no shoulder on the road as it crosses the river, so it is not safe to stop while on the bridge.
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The beach is located inside of Greenwich Point Park which requires you to purchase a ticket for entry. The beach itself is great and has everything you'll need for a day of sun, sand, & swimming. Bring your own lunch or try some of the beach concessions. This is a great place to bring the family.
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Along the coast of Connecticut you'll a small portion of the 3,000 mile East Coast Greenway. The ECG runs through 15 states & Washington D.C. with a stated goal of connecting people to each other and to a healthy active lifestyle.
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Port Chester offers a diverse selection of over 15 road cycling routes. These routes cater to various fitness levels, with 3 easy routes, 11 moderate routes, and 4 challenging routes designed for experienced cyclists.
Yes, for beginners or those seeking a relaxed ride, the region offers several easy options. A notable one is the Playland Lake – Red Mill at Kirby Tidal Pond loop, which is just over 20 kilometers with minimal elevation gain, making it suitable for any fitness level.
Road cycling routes around Port Chester offer varied landscapes, including picturesque reservoirs like Byram Lake Reservoir, Titicus Reservoir, and Cross River Reservoir. You'll also encounter rolling hills, coastal areas, and stretches of quiet roads, providing diverse scenery throughout your ride.
Absolutely. For experienced cyclists seeking a significant challenge, the Titicus Reservoir South Side – Cross River Reservoir loop from Port Chester is a demanding 117.7 km route with over 1,200 meters of elevation gain. Another difficult option is the North County Trailway – New Croton Dam loop from Port Chester, covering 112.9 km with similar elevation.
The road cycling routes in Port Chester are highly rated by the komoot community, with an average score of 5.0 stars. Cyclists frequently praise the varied terrain, which includes both reservoir-side roads and rolling hills, and the options available for different ability levels. The network extending into Westchester County and Connecticut also offers diverse scenery.
Yes, many routes offer scenic points and nearby attractions. You might pass by the historic Old Croton Aqueduct Trail or enjoy views of the Hudson River from areas like Lenoir Preserve. The region also features several reservoirs, such as Kensico Reservoir and Playland Lake, which provide beautiful backdrops for your ride.
While many road cycling routes involve varied terrain and some elevation, families looking for flatter, paved options might consider sections of the Bronx River Greenway or the South County Trailway. These trails are known for their scenic views and well-maintained surfaces, offering a more relaxed experience away from traffic.
Yes, many of the road cycling routes around Port Chester are designed as loops, allowing you to start and end at the same point. Examples include the popular Milbank Conservation Easement – Round Hill Community Church loop from Port Chester and the Round Hill Community Church – New York–Connecticut Border loop from Port Chester.
The varied terrain of Port Chester makes it suitable for cycling across multiple seasons. Spring and fall offer pleasant temperatures and beautiful foliage, while summer provides longer daylight hours. Always check local weather conditions before heading out, as some routes may have unpaved segments that can be affected by rain.
Westchester County is rich in parks and preserves. While some, like Cranberry Lake Preserve, are not suitable for bikes, others offer excellent cycling opportunities. The Old Croton Aqueduct Trail, Bronx River Greenway, and South County Trailway are popular choices, providing paved or well-maintained paths for cyclists. For more information on parks in the region, you can visit Visit Westchester NY.
While specific cafes are not always directly on every route, Port Chester and the surrounding towns offer various amenities. Many routes pass through or near communities where you can find places to stop for coffee or a meal. Planning your route with komoot can help you identify towns and potential stops along the way.
For a balanced challenge, consider the Byram River Marina – Byram Lake Reservoir loop from Port Chester, a 48.7 km route with approximately 530 meters of elevation gain. Another great option is the Milbank Conservation Easement – Round Hill Community Church loop from Port Chester, which is 63.1 km with 560 meters of climbing.


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