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Routes
Road cycling routes
United States
Connecticut
Southeastern Connecticut Planning Region

Stonington

The best road cycling routes around Stonington

4.8

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447

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Road cycling around Stonington, Connecticut, offers diverse terrain across its coastal landscapes and inland areas. The region features mostly flat routes along the shoreline, providing views of Fishers Island Sound and Block Island Sound. Cyclists can also explore scenic back roads that traverse farms and gentle hills. This combination of coastal and rural environments provides varied experiences for road cyclists.

Best road cycling routes around Stonington

  • The most popular road cycling route is Watch Hill Point – Maschaug Pond loop…

Last updated: July 12, 2026

5.0

(1)

49

riders

#1.

Watch Hill Point – Maschaug Pond loop from Stonington

56.3km

02:22

280m

280m

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

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Moderate

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

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

Easy

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

Easy

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

Easy
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Popular around Stonington

Hiking around Stonington

Cycling around Stonington

Running Trails around Stonington

Tips from the Community

Alex
February 19, 2024, Union Baptist Church

The church is an impressive sight from the roadside, with the architecture towering over the street. It is popular within the local community, and makes a great photo along your ride.

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For cyclists crossing the Mystic River Bascule Bridge, the view is nothing short of captivating. From this vantage point, you're treated to a picturesque scene of the serene Mystic River below. As you pedal across, you can admire the rhythmic motion of boats gliding through the water and the charming waterfront architecture lining the riverbanks. The bridge itself, with its impressive mechanical design, adds to the allure of the experience, providing cyclists with both a visual feast and a sense of the area's industrial heritage.

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Napatree Beach and Peninsula is a very picturesque and charming place. Busy in summer time, on one side you can see all the moored boats and on the other side you will have the beach to enjoy.

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There are four parcels of beachfront land set aside here for the private community of Groton Long Point. However, you can still enjoy the great views over the water as you pedal past.

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The Pawcatuck River will soon finish its journey at Little Narragansett Bay. Here, as you cycle down River Road, the river starts to open up, and you will see more leisure craft on the water. The views become more beautiful and expansive the closer you get to the sea.

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The Perkins Wildlife Corridor has an interesting array of trees and ponds that you can see some of from the road or more comprehensively if you step off the bike and take a break.

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Ride along South Shore Avenue and take in the great views from the beach all the way to Fisher Island in the distance.

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Fennerswood Preserve O'Neill Tract is a retreat into nature and provides a remote and quiet background whilst cycling on the road through it. Keep your eyes peeled for the birdlife in the trees around you.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Stonington?

Road cycling around Stonington, Connecticut, offers a mix of terrain. You'll find mostly flat routes along the picturesque shoreline, providing stunning views of Fishers Island Sound and Block Island Sound. For those seeking a different experience, there are also scenic back roads that traverse farms and gentle hills, particularly in areas like North Stonington. This combination provides varied experiences for cyclists of all levels.

Are there any easy road cycling routes suitable for beginners in Stonington?

Yes, Stonington offers several easy routes perfect for beginners or those looking for a relaxed ride. For instance, the Watch Hill Point – Maschaug Pond loop from Watch Hill is an easy 16.4-mile path that provides scenic coastal views along the shoreline. The region's coastal paths are generally less challenging.

What are some scenic viewpoints or natural features I can see while road cycling in Stonington?

Stonington's routes are rich with scenic beauty. You can enjoy panoramic vistas from Watch Hill Point, looking out to the Atlantic Ocean and Block Island Sound. Many routes offer views of Fishers Island Sound. The Watch Hill Point – Maschaug Pond loop from Stonington, for example, offers extensive coastal views. You might also pass by areas like the Barn Island Wildlife Management Area, known for its salt marshes and wildlife.

Are there any circular road cycling routes in Stonington?

Yes, many of the road cycling routes in Stonington are designed as loops, allowing you to start and end in the same location. Examples include the popular Watch Hill Point – Maschaug Pond loop from Stonington and the Old Mystic – Mystic River Waterfront loop from Mystic. These circular routes make planning your ride convenient.

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

The spring, summer, and fall months generally offer the best conditions for road cycling in Stonington. During these seasons, the weather is typically pleasant, and the coastal views are at their most vibrant. Summer can be warm, but coastal breezes often provide relief. Fall brings beautiful foliage to the inland routes.

Are there any family-friendly road cycling options in Stonington?

Stonington is known for its accessibility, including initiatives like 'Cycling Without Age' which provides outdoor cycling experiences for people of all ages and abilities. Many of the flatter, coastal routes, such as the Watch Hill Point – Maschaug Pond loop from Watch Hill, are suitable for families looking for a less strenuous ride.

What do other road cyclists enjoy most about cycling in Stonington?

The area is highly rated by the komoot community, with an average score of 4.75 stars from over 10 reviews. Reviewers often praise the diverse terrain, from scenic coastal paths to quiet back roads, and the beautiful views of the sounds and historic towns. The variety of routes catering to different ability levels is also frequently highlighted.

Can I find cafes or pubs along the road cycling routes in Stonington?

Yes, many routes in Stonington pass through or near charming towns like Mystic, Groton Long Point, Noank, and Stonington village. These areas offer opportunities to stop at local cafes, restaurants, and pubs. The Historic Stonington Borough, in particular, is known for its amenities and historic charm.

Are there any longer distance road cycling routes available in Stonington?

For cyclists looking for a longer ride, Stonington offers routes that can extend your journey. The Watch Hill Point – Maschaug Pond loop from Mystic is a moderate 87.2-mile route, providing a more extensive exploration of the region's coastal and inland landscapes.

What kind of historical landmarks or points of interest can I explore while cycling in Stonington?

Stonington is rich in history. You can cycle through the Historic Stonington Borough, known for its beautifully preserved colonial, Federal, and Greek revival architecture. The Stonington Harbor Light, now a museum, is another notable landmark. Routes often pass through towns like Mystic, which also boasts historical significance.

How many road cycling routes are available in Stonington?

There are over 90 road cycling routes available around Stonington, offering a wide range of options for different skill levels and preferences. This includes 35 easy routes and 62 moderate routes, ensuring there's something for everyone.

Are there specific routes that explore local wineries in Stonington?

Yes, for those interested in a leisurely ride with a unique stop, there are routes designed to explore local wineries such as Saltwater Farm, Jonathan Edwards, and Stonington Vineyards. These routes offer a pleasant combination of cycling and local flavor.

Most popular routes around Stonington

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