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Routes
Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Old Greenwich

The best road cycling routes around Old Greenwich

4.6

(22)

1,065

riders

14

rides

Road cycling around Old Greenwich offers routes through coastal areas, well-maintained parks, and sections of the East Coast Greenway. The terrain is generally gentle, with some routes featuring moderate elevation gains. The region is characterized by its proximity to the Long Island Sound and various green spaces like Binney Park and Greenwich Point Park. These features provide varied backdrops for road cycling, from waterfront paths to tree-lined park roads.

Best road cycling routes in Old Greenwich

  • The most popular road…

Last updated: May 4, 2026

14

riders

#1.

East Coast Greenway – Taconic Road loop from Old Greenwich

60.5km

03:04

680m

680m

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

Moderate

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

Moderate

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

Easy
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Popular around Old Greenwich

Hiking around Old Greenwich

Cycling around Old Greenwich

Running Trails around Old Greenwich

Tips from the Community

Zachary
June 18, 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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A calm pond, surrounded by lush greenery, has a road winding along it the entire way. In the winter, you'll see some ice skaters on the lake as well.

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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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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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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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mtm05005
January 1, 2025, Cove Island Park

Cove Island Park is a popular park and beach in Stamford. It is on the Long Island Sound and offers great views of the water and nearby Brush Island. It also has a walking trail, a playground, and a cycling path.

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mtm05005
February 20, 2024, Brown Preserve

Brown Preserve is a beautiful, protected woodland that Stanwich Road runs through. It is a great section of shady road to ride through, especially on a hot summer's day.

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Lisa
February 20, 2024, Newman Mills Park

This 7.6-acre park used to be a grist mill, but now it's a tiny gem along the Mianus River. You'd need a parking sticker to leave your car here, but biking here is free.

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Frequently Asked Questions

How many road cycling routes are available around Old Greenwich?

Old Greenwich offers a wide selection of road cycling routes, with over 160 options available. These routes cater to various skill levels, from easy rides to more challenging excursions.

What kind of terrain can I expect when road cycling in Old Greenwich?

The terrain in Old Greenwich is generally gentle, featuring well-paved surfaces suitable for road cycling. You'll find routes that traverse coastal areas, well-maintained parks, and segments of the East Coast Greenway. While many routes are relatively flat, some do include moderate elevation gains, particularly as you venture further from the immediate coastline.

Are there any easy road cycling routes suitable for beginners or families in Old Greenwich?

Yes, Old Greenwich has several easy road cycling routes perfect for beginners or families. For instance, the Binney Park – East Coast Greenway loop from Cos Cob is an easy 9-mile ride offering a blend of park scenery and the East Coast Greenway. Another great option is the East Coast Greenway – Greenwich Point Beach loop from Old Greenwich, which provides coastal views along Greenwich Point Park.

What are some notable landmarks or scenic viewpoints I can see while cycling in Old Greenwich?

Road cycling in Old Greenwich offers many scenic opportunities. You can enjoy stunning views of the Long Island Sound, especially along routes that pass through Greenwich Point Park. Other picturesque spots include Binney Park with its stone bridges and gazebo, and the maritime charm around the Old Greenwich Yacht Club. The East Coast Greenway itself offers continuous scenic stretches.

Are there any longer or more challenging road cycling routes for experienced cyclists?

For experienced cyclists seeking a longer ride, the East Coast Greenway – Binney Park loop from Old Greenwich is a moderate 37.5-mile route with significant elevation gain. Another option is the Binney Park – Mianus River Reservoir loop from Old Greenwich, a 23.9-mile moderate trail that takes you through Binney Park and near the Mianus River Reservoir, offering a good workout.

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

Old Greenwich is generally pleasant for road cycling from spring through fall. The weather is typically mild, making for comfortable rides. While winter cycling is possible, be mindful of colder temperatures and potential icy conditions, especially on less-trafficked roads.

Can I find loop routes for road cycling in Old Greenwich?

Yes, many road cycling routes in Old Greenwich are designed as loops, allowing you to start and end at the same point. Examples include the Binney Park – East Coast Greenway loop from Cos Cob and the East Coast Greenway – Greenwich Point Beach loop from Old Greenwich, both offering circular paths to explore the area.

Are there any parks or natural areas accessible by road bike in Old Greenwich?

Absolutely. Greenwich Point Park and Binney Park are both excellent for road cycling, offering scenic paths and well-maintained surfaces. While Mianus River Park is better suited for mountain or hybrid bikes due to its trails, the roads leading to and around it provide a scenic cycling experience.

What do other road cyclists enjoy most about cycling in Old Greenwich?

The road cycling routes in Old Greenwich are highly rated by the komoot community, with an average score of 4.6 stars from over 20 reviews. Cyclists frequently praise the beautiful coastal paths, the well-maintained park roads, and the accessibility of the East Coast Greenway, which offers varied backdrops for rides.

Are there any attractions or points of interest near the cycling routes?

Yes, several attractions are close to the cycling routes. You can visit Greenwich Point Beach for coastal views, or explore Mianus River Natural Park for a change of scenery. The East Coast Greenway itself is a major point of interest, connecting various parts of the region.

Is public transport available to access road cycling routes in Old Greenwich?

Old Greenwich has public transport options, including train services, which can help you access various parts of the region. It's advisable to check local schedules and policies regarding bikes on public transport to plan your journey effectively.

Where can I find parking for road cycling routes in Old Greenwich?

Parking is generally available at key access points for parks and trails in Old Greenwich. For specific details on parking at locations like Greenwich Point Park or Binney Park, it's recommended to check the respective park websites or local municipal information for any permit requirements or restrictions.

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