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Road cycling routes
United States
New York
Suffolk County

Fishers Island

The best road cycling routes around Fishers Island

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Road cycling around Fishers Island features routes that traverse coastal areas and offer views of the surrounding waters. The terrain generally includes gentle undulations, with some routes following riverfronts and passing through local communities. Elevations are typically low, making for accessible cycling. The island's landscape provides a mix of open stretches and scenic points of interest suitable for road cyclists.

Best road cycling routes around Fishers Island

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

Last updated: July 16, 2026

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#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

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Popular around Fishers Island

Hiking around Fishers Island

Running Trails around Fishers Island

Cycling around Fishers Island

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

How many road cycling routes are available around Fishers Island?

There are over 70 road cycling routes available around Fishers Island, offering a variety of options for different skill levels. The komoot community has explored these routes over 300 times.

Are there any easy road cycling routes suitable for beginners or families?

Yes, Fishers Island offers several easy road cycling routes. A great option is the Old Mystic – Mystic River Waterfront loop from Mystic, an easy 21.1-mile path that follows the Mystic River, providing scenic views. Another accessible route is the Mystic River Bascule Bridge – Union Baptist Church loop from Mystic, a 14.9-mile trail through local landmarks.

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

Road cycling around Fishers Island features routes that traverse coastal areas and offer views of the surrounding waters. The terrain generally includes gentle undulations, with some routes following riverfronts and passing through local communities. Elevations are typically low, making for accessible cycling.

Are there any longer distance road cycling routes for more experienced riders?

For those looking for a longer ride, the Watch Hill Point – Maschaug Pond loop from Stonington is a moderate 35.0-mile route that takes approximately 2 hours 21 minutes to complete, offering views of coastal points and a pond. Another moderate option is the Union Baptist Church – Hoxie Scenic Overlook loop from Groton, spanning 53.2 miles.

What are some scenic viewpoints or attractions I can see along the road cycling routes?

Many routes offer scenic views. You can pass by Watch Hill Point, known for its coastal vistas, or the Hoxie Scenic Overlook. The Old Mystic – Mystic River Waterfront loop from Mystic provides continuous scenic views along the Mystic River.

Are there any circular road cycling routes around Fishers Island?

Yes, many of the routes around Fishers Island are designed as loops. For instance, the Watch Hill Point – Maschaug Pond loop from Stonington and the Mystic River Bascule Bridge – Union Baptist Church loop from Mystic are both popular circular routes.

What is the best season for road biking around Fishers Island?

Given its coastal location, spring and fall generally offer pleasant temperatures and fewer crowds, making them ideal seasons for road biking around Fishers Island. Summer can also be enjoyable, though it may be warmer and busier.

Are there any challenging or advanced road cycling routes in the area?

While there are no routes classified as 'difficult' in this area, there are several moderate routes that offer longer distances and more elevation gain for those seeking a greater challenge. The Old Mystic – Mystic River Waterfront loop from Haley Farm State Park, for example, covers 49 miles with over 430 meters of elevation gain.

What do other road cyclists enjoy most about road cycling in Fishers Island?

The area is highly rated by the komoot community, with an average score of 4.6 stars. Reviewers often praise the scenic coastal paths, riverfront routes, and the variety of options suitable for different ability levels.

Is there public transport available to access road cycling routes near Fishers Island?

Access to Fishers Island itself is primarily by ferry. For routes on the mainland near Fishers Island, public transport options may vary by specific starting point. It's advisable to check local bus or train schedules for towns like Mystic or Stonington, which are common starting points for many routes.

Where can I find parking for road cycling routes around Fishers Island?

Parking availability will depend on your chosen starting point. Many routes begin in towns like Stonington or Mystic, where public parking lots or street parking may be available. For specific routes, checking the komoot tour details or local municipal websites for parking information is recommended.

Are there any unique or less-traveled road cycling routes to discover?

While many routes offer popular scenic views, exploring some of the less-frequented paths can reveal hidden gems. Consider routes that venture slightly inland from the immediate coast to discover quieter roads and local communities, offering a different perspective of the region.

Most popular routes around Fishers Island

Easy hikes around Fishers Island

Most popular attractions around Fishers Island

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