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Routes
Cycling routes
United States
Connecticut
Western Connecticut Planning Region

New Canaan

The best cycling routes around New Canaan

4.8

(32)

193

riders

52

rides

Touring cycling around New Canaan offers a diverse landscape characterized by rolling hills, scenic river valleys, and access to coastal areas. The region features a mix of suburban roads, dedicated trails, and routes that pass by reservoirs and beaches. Elevations are generally moderate, with some routes including gradual climbs. This varied terrain provides a range of experiences for touring cyclists.

Best touring cycling routes around New Canaan

  • The most popular touring cycling route is New Canaan to Pear Tree Point…

Last updated: April 25, 2026

5

riders

#1.

Norwalk River Valley Trail

14.0km

00:49

20m

20m

An easy 8.7-mile touring cycling route on the Norwalk River Valley Trail in Calf Pasture Beach Park, featuring diverse urban and natural sce

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Easy

3.0

(1)

3

riders

Cycle the moderate 31-mile New Canaan to Pear Tree Point Beach loop, enjoying coastal views and charming town scenery.

Moderate
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5.0

(2)

2

riders

Cycle the moderate 20.2-mile Talmadge Hill to Crescent Beach loop, enjoying coastal views and varied scenery through Noroton and Rowayton.

Moderate

5.0

(2)

3

riders

Cycle the difficult 30.5-mile Siscowit & South Norwalk Reservoir loop, gaining 1532 feet through varied terrain and scenic views.

Hard

This moderate 25.2-mile touring cycling loop from New Canaan, CT to Bedford, NY offers scenic rolling hills and historic charm.

Moderate
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Popular around New Canaan

Hiking around New Canaan

Road Cycling Routes around New Canaan

Running Trails around New Canaan

Tips from the Community

Felix
July 18, 2025, South Norwalk Reservoir

Beautiful reservoir and bridge across it (Old Huckleberry Rd). The approach through Old Kingdom Road, Reservoir Rd and Old Huckleberry on very narrow, windy and hilly roads is beautiful as well.

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This is a popular beach on Long Island Sound with picnic areas, benches, and a paved path. It's a great place to run with a nice view of the water.

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Scott
September 12, 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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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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Thanks to over a century of dedicated work by the Bedford Historical Society this town has a number of well preserved buildings plus multiple museums and education programs for locals & tourists alike.

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Andrus
January 2, 2024, Ring's End Bridge

The current bridge was built nearly a century ago and replaced previous bridges that have crossed this span since at least 1825.

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Tyler Sanders
November 19, 2023, Waveny Park

The main focal point of the park is Waveny House, a castle constructed in 1912. This location has featured in numerous movies and TV shows, including All My Children.

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Andrus
September 13, 2023, South Norwalk Reservoir

Beautiful spot to take a break and enjoy the scenery. There's plenty of trees nearby to have a shady rest and snack/water break as well.

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Frequently Asked Questions

How many touring cycling routes are available around New Canaan?

There are over 50 touring cycling routes mapped around New Canaan, offering a wide variety of experiences for different skill levels.

Are there easy touring cycling routes suitable for beginners or families in New Canaan?

Yes, New Canaan offers 14 easy touring cycling routes. A great option for a relaxed ride is the Norwalk River Valley Trail, which follows a scenic river valley and is relatively flat and accessible.

What kind of terrain can I expect on touring cycling routes in New Canaan?

The region features a diverse landscape with rolling hills, scenic river valleys, and routes that provide access to coastal areas and reservoirs. You'll find a mix of suburban roads and dedicated trails, with elevations generally moderate, though some routes include gradual climbs.

Are there any challenging touring cycling routes for experienced riders?

Yes, for more experienced touring cyclists, there are 11 difficult routes. The Siscowit & South Norwalk Reservoir loop is a demanding option, covering nearly 50 km with significant elevation changes.

What are some interesting places to see along the touring cycling routes?

Many routes offer scenic views and pass by notable attractions. You might cycle past the South Norwalk Reservoir, or historic sites like the Lockwood-Mathews Mansion Museum. The New Canaan to Pear Tree Point Beach loop offers coastal views.

Are there touring cycling routes that form a loop?

Yes, many routes in New Canaan are designed as loops. For example, the Talmadge Hill to Crescent Beach loop takes you through varied suburban and coastal landscapes, while the Siscowit Reservoir & New Canaan loop explores reservoir areas.

Where can I find places to eat or drink near the cycling routes?

New Canaan and its surrounding areas offer various spots for refreshments. Some routes pass close to local establishments, such as Kneads Bakery, which is a popular cafe in the area.

What do other touring cyclists say about the routes in New Canaan?

The touring cycling routes in New Canaan are highly rated by the komoot community, with an average score of 4.8 stars from over 27 reviews. Cyclists often praise the diverse scenery, from rolling hills to coastal stretches, and the variety of routes available for different skill levels.

What is the best time of year to go touring cycling in New Canaan?

Spring and fall generally offer the most pleasant conditions for touring cycling in New Canaan, with mild temperatures and beautiful foliage. Summer can also be enjoyable, especially on routes with shade or coastal breezes, but be prepared for warmer weather.

Are there any less crowded or 'hidden gem' touring cycling routes in the area?

While specific crowd levels vary, exploring some of the moderate or difficult routes, or those slightly further from the town center, might offer a more secluded experience. The region's 50+ routes provide ample opportunity to discover less-traveled paths.

Is public transport available to access the touring cycling routes in New Canaan?

New Canaan has a Metro-North train station, which can provide access to the town. From there, you can connect to various routes. It's advisable to check the specific route starting points and public transport schedules for the most convenient access.

Can I bring my dog on the touring cycling routes?

While many routes are on public roads or shared paths, specific regulations regarding dogs can vary by park or trail section. It's best to check local signage or the specific rules for any parks or natural areas you plan to cycle through with your dog.

Most popular routes around New Canaan

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