New Canaan to Pear Tree Point Beach loop
New Canaan to Pear Tree Point Beach loop
4.6
(4052)
13,228
riders
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
Start point
Train Station
Get Directions
115Β m
Highlight β’ Settlement
Tip by
25.0Β km
Highlight β’ Bridge
Tip by
26.2Β km
Highlight β’ Beach
Tip by
35.4Β km
Highlight β’ Beach
Tip by
50.0Β km
End point
Train Station
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
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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This route was planned by komoot.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Yes, the route also passes through sections of the East Coast Greenway (CT) and the Baker park trail.
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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