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Routes
Road cycling routes
United States
Connecticut
Northwest Hills Planning Region

Sharon

The best road cycling routes around Sharon

3.0

(5)

230

riders

26

rides

Road cycling around Sharon, Massachusetts, offers varied terrain characterized by rolling hills and wooded neighborhoods. The town's geography includes significant natural features such as Lake Massapoag, a 353-acre body of water, which provides scenic backdrops for many routes. Over 5,000 acres of protected land, including the Moose Hill Wildlife Sanctuary, contribute to the area's natural beauty, featuring wetlands and forests. These elements create a diverse environment for road cyclists seeking different levels of challenge.

Best road cycling routes around Sharon

Last updated: May 17, 2026

3.5

(2)

37

riders

#1.

Wassiac Rail Station – Wassiac Bridge over a Creek loop from Millerton

36.8km

01:57

170m

170m

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

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Easy

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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24

riders

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

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

Moderate
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Popular around Sharon

Hiking around Sharon

Cycling around Sharon

Tips from the Community

Alex Tray
June 8, 2024, Wassiac Bridge over a Creek

Near and artist commune

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Wonderful food and rest stop at the end of the trail

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Train goes to and from NYC

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View of a pond and wildlife

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Scott
February 27, 2024, Lakeville

Nestled in the Litchfield Hills of Connecticut, Lakeville is a charming small town known for its scenic beauty. The town is surrounded by rolling hills, forests, and several lakes, including Lake Wononscopomuc, which is the largest natural lake in the state.

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Frequently Asked Questions

How many road cycling routes can I explore around Sharon?

Sharon offers a diverse network of over 25 road cycling routes, catering to various skill levels. These routes are highly regarded by the komoot community, with more than 240 road cyclists having used komoot to discover the area's varied terrain.

What kind of terrain can I expect on road cycling routes in Sharon?

Road cycling in Sharon is characterized by rolling hills and wooded neighborhoods, providing a mix of challenges and scenic beauty. You'll find routes with varied elevation gains, from gentle gradients suitable for leisurely rides to more challenging climbs, often passing by natural features like Lake Massapoag.

Are there any easy or beginner-friendly road cycling routes in Sharon?

Yes, Sharon has several easy road cycling options. For instance, the Wassiac Rail Station – Wassiac Bridge over a Creek loop from Village of Millerton is an easy 22.9-mile route featuring gentle gradients through rural landscapes. Another easy option is the Wassiac Rail Station – Wassiac Bridge over a Creek loop from Sharon Station, which is 21.3 miles long.

What are some scenic highlights or attractions I can see while road cycling in Sharon?

Many routes offer picturesque views of Lake Massapoag, a significant 353-acre body of water. You can also cycle through areas near the Moose Hill Wildlife Sanctuary, known for its protected wetlands and forests, or connect to roads that pass by Borderland State Park, home to the historic Ames Mansion.

What do other road cyclists enjoy most about the routes in Sharon?

The road cycling routes in Sharon are highly rated by the komoot community, with an average score of 3.8 stars. Reviewers often praise the area's 'classic New England back roads,' the moderate terrain, and the scenic views, particularly around Lake Massapoag and through wooded areas.

Are there any circular road cycling routes in the Sharon area?

Yes, many routes in Sharon are designed as loops, allowing you to start and end at the same point. Examples include the Candy-O's Candy & Collectibles loop from Benton Hill Preserve, a moderate 18.6-mile path, and the Rail trail bridge loop from Coleman Station, a 20.8-mile trail through varied terrain.

Is Sharon suitable for family-friendly road cycling?

Sharon offers routes with varying difficulty levels, including several easy options with gentle gradients that can be suitable for families. The presence of mostly paved surfaces and low elevation gain around areas like Lake Massapoag makes them accessible for different fitness levels. Always check the specific route details for distance and elevation to ensure it matches your family's capabilities.

What is the best time of year for road cycling in Sharon?

The spring, summer, and fall months generally offer the best conditions for road cycling in Sharon. Fall, in particular, is popular for its stunning fall foliage, which adds an extra layer of beauty to the wooded routes. While winter cycling is possible, riders should be prepared for colder temperatures and potential icy conditions.

Are there places to park near the road cycling routes in Sharon?

While specific parking information for each route varies, many popular cycling areas and trailheads in Sharon, such as those near Lake Massapoag or Borderland State Park, typically offer designated parking facilities. It's advisable to check local regulations or specific route starting points for parking availability.

Are there any cafes or pubs near the road cycling trails in Sharon?

Sharon has a local community with various amenities. While specific establishments directly on every trail may vary, you can find cafes and pubs within the town center or nearby areas that are easily accessible from many cycling routes, perfect for a post-ride refreshment.

Are there any permits required for casual road cycling in Sharon?

Generally, casual road cycling on public roads and designated bike paths in Sharon does not require special permits. However, if your route takes you through specific state parks or private lands, it's always a good idea to check their individual regulations regarding access or permits.

How challenging are the road cycling routes in Sharon?

Sharon's road cycling routes range from easy to difficult. You'll find 5 easy routes, 17 moderate routes, and 3 difficult routes. This variety ensures that both beginners and experienced riders can find suitable challenges, with options featuring rolling hills and varied elevation profiles.

Most popular routes around Sharon

Hiking around Sharon

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