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Bike touring routes & trails
United States
Connecticut
Western Connecticut Planning Region
New Canaan

New Canaan to Pear Tree Point Beach loop

Moderate

4.6

(4052)

13,228

riders

New Canaan to Pear Tree Point Beach loop

03:01

50.0km

370m

Cycling

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

Last updated: February 26, 2026

Waypoints

A

Start point

Train Station

Get Directions

1

115Β m

New Canaan

Highlight β€’ Settlement

New Canaan is a wealthy little town about an hour's train ride away from Manhattan.

Tip by

2

25.0Β km

Ring's End Bridge

Highlight β€’ Bridge

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

Tip by

3

26.2Β km

Pear Tree Point Cove

Highlight β€’ Beach

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, …

Tip by

4

35.4Β km

Crescent Beach

Highlight β€’ Beach

Riding on Crescent Beach Road, you get lovely views of the Long Island Sound.

Tip by

B

50.0Β km

End point

Train Station

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Way Types & Surfaces

Way Types

29.2Β km

18.8Β km

1.34Β km

636Β m

Surfaces

31.3Β km

18.4Β km

268Β m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (130Β m)

Lowest point (0Β m)

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Weather

Powered by Foreca

Today

Tuesday 7 July

21Β°C

16Β°C

88Β %

Additional weather tips

Max wind speed: 16.0Β km/h

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Frequently Asked Questions

How long does it typically take to complete this cycling loop?

The New Canaan to Pear Tree Point Beach loop is approximately 50 kilometers (31 miles) long. Cyclists generally complete it in about 3 hours, though this can vary based on your pace and stops along the way.

What is the difficulty level of this cycling route?

This route is classified as moderate. It requires a good level of fitness due to its length and an elevation gain of about 370 meters. It's not considered an easy ride, so some cycling experience is beneficial.

What kind of terrain can I expect on the cycling route?

The route primarily features paved surfaces, with about 31.3 kilometers of asphalt and 18.4 kilometers of other paved types. However, be aware that some short segments, approximately 268 meters, have an unknown surface type and could be unpaved or challenging to ride.

What are the main points of interest along the New Canaan to Pear Tree Point Beach loop?

You'll pass through the charming town of New Canaan and cross the historic Ring's End Bridge. A significant highlight is Pear Tree Point Cove, a sheltered inlet known for its birdlife. Riding along Crescent Beach Road offers lovely views of the Long Island Sound, leading to Pear Tree Point Beach itself, which provides breathtaking views and a peaceful atmosphere.

Where can I park when cycling this route?

Parking is available at Pear Tree Point Beach, which is well-equipped with amenities. It's a convenient starting and ending point for the loop. For specific parking regulations or fees, it's advisable to check local town resources.

What is the best time of year to cycle this loop?

The best time to cycle this loop is generally during the spring, summer, and fall months. These seasons offer pleasant weather for enjoying the coastal views and the amenities at Pear Tree Point Beach. Autumn provides particularly picturesque scenery with changing foliage.

Are there any permits or entrance fees required for this route or Pear Tree Point Beach?

While there are no specific permits required for cycling the general route, Pear Tree Point Beach itself is an eight-acre park. Access to the beach and its amenities, especially during peak season, may require a fee or resident pass. It's best to check the official Darien town website or local visitor guides like connecticutvisitorguide.com or ctvisit.com for current information.

Is the New Canaan to Pear Tree Point Beach loop dog-friendly?

The cycling route itself generally follows public roads and paths, where dogs on a leash are typically allowed. However, specific rules apply to Pear Tree Point Beach. While it's a popular park, dog access to the beach area may be restricted, especially during peak season or certain hours. Always check local signage or the town's official website for the most up-to-date pet policies.

Are there amenities like restrooms or food available along the route?

Pear Tree Point Beach is well-equipped with amenities, including picnic areas, restrooms, and a concession stand during peak season. As the route passes through New Canaan and other developed areas, you'll find various cafes and shops for refreshments and supplies.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the East Coast Greenway (CT) and the Baker park trail.

What makes Pear Tree Point Beach a notable stop on this loop?

Pear Tree Point Beach is an eight-acre park offering breathtaking views of the Long Island Sound, a pristine shoreline, and a peaceful atmosphere. It's ideal for watching boats, enjoying spectacular sunsets, and features amenities like a boat launch, a gazebo, and community events. Its commitment to environmental sustainability also makes it a well-regarded spot for both locals and visitors.

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