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Routes
Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Cannondale

The best road cycling routes around Cannondale

5.0

(3)

482

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92

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Road cycling around Cannondale features a landscape characterized by rolling hills and scenic water bodies, including the Saugatuck Reservoir and Held Pond. The region offers varied terrain suitable for road bikes, with routes that traverse local parks and provide views of the surrounding natural environment. Elevations are moderate, with climbs typically under 500 meters, making it accessible for different fitness levels. The area's road network allows for circular routes exploring these features.

Best road cycling routes around Cannondale

  • The most…

Last updated: May 20, 2026

14

riders

#1.

View of Saugatuck Reservoir – Keene Park loop from Wilton Center

29.3km

01:22

250m

250m

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

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Easy

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

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

Moderate

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

Moderate

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

Moderate
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Popular around Cannondale

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Tips from the Community

Jamie S.
February 26, 2024, Biddle Hill

Biddle Hill is a 732-foot hill on Branchville Road. This is a nice climb in a quiet area and a good addition to any ride.

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At this spot Silver Springs Swamp flows over a small dam into a small stream. This is a very pretty place to ride past as you explore the area.

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If you look to the south while cycling along the road, you can see Held Pond, a beautiful 31.4-acre pond that, unfortunately, is only accessible to the residents living along its shore. The origin of this pond is a former rock quarry that was filled with water.

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Javi Jaavii
January 26, 2024, Keene Park

If you're riding along River Rd, you'll come across Keene Park, a quiet and secluded park next to the Saugatuck River. It features a small playground for children and offers the opportunity to explore the wooded area by foot.

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Alex
December 30, 2023, Marvin Tavern

The Marvin Tavern, also known as Matthew Marvin House, has been on the National Register of Historic Places since 1984. It is a historic building 2 and a half stories tall. It was built in 1760 with impressive woodwork. It is privately owned today but can be seen from the street.

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This is a beautiful National Historic Site that contains the immaculately preserved Weir house, barn and art studios. A stunning setting among more than 60 acres of woods, fields, and waterways. Take some time to visit the home and studio of America's most beloved Impressionist, J. Alden Weir.

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Lisa
November 16, 2023, Deer Run Pond

Want a break from a scenic ride along Nod Road or nearby Whipstick Road? Pull off onto Nod West Drive for a few moments beside this small pond.

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Very steep downhill leads right into a light uphill.

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Frequently Asked Questions

What kind of difficulty levels can I expect on road cycling routes around Cannondale?

Cannondale offers a diverse range of road cycling routes suitable for various fitness levels. You'll find approximately 19 easy routes, 58 moderate routes, and 17 more challenging options, catering to both beginners and experienced cyclists.

Are there any family-friendly road cycling routes in Cannondale?

Yes, there are several easy road cycling routes around Cannondale that are suitable for families. These routes typically feature moderate elevations and pass through scenic areas like local parks. One popular easy route is the View of Saugatuck Reservoir – Keene Park loop from Wilton, which is 18.3 miles long.

What are the most scenic viewpoints along the road cycling routes in Cannondale?

Many routes in Cannondale offer picturesque views, particularly of the region's water bodies. You can enjoy stunning vistas of the Saugatuck Reservoir and Held Pond. Routes like the View of Saugatuck Reservoir – View of Held Pond loop from Wilton specifically connect these beautiful natural landmarks.

Are there circular road cycling routes available in Cannondale?

Yes, the road network around Cannondale is well-suited for circular routes. Many of the most popular options are loops, allowing you to start and finish at the same point while exploring the rolling hills, reservoirs, and parks. Examples include the View of Held Pond – View of Saugatuck Reservoir loop from Cannondale.

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

The komoot community highly rates road cycling in Cannondale, with an average score of 4.9 stars from nearly 40 reviews. Cyclists often praise the varied terrain, the scenic views of reservoirs and parks, and the accessibility of routes for different ability levels.

What are some notable natural attractions to see while road cycling in Cannondale?

While cycling, you'll encounter beautiful natural features such as the South Norwalk Reservoir, the Saugatuck Reservoir, and the Siscowit Reservoir. These water bodies are central to many of the area's most scenic routes.

Are there any historical sites or cultural landmarks near the road cycling routes?

Yes, beyond the natural beauty, you can find cultural points of interest. For example, Weir Farm National Historical Park is an attraction in the wider Cannondale area that offers a glimpse into American art and history.

What is the best time of year for road biking in Cannondale?

The region's moderate elevations and varied terrain make it enjoyable for road cycling across multiple seasons. Spring and fall typically offer pleasant temperatures and vibrant scenery, while summer provides longer daylight hours. Winter conditions would require appropriate gear due to potential colder weather.

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

Yes, for those seeking a greater challenge, Cannondale offers routes with more significant elevation gains. For instance, the Ferris Hill – Wren Knolls loop from Morgan Cemetery is a moderate route spanning over 43 km with an elevation gain of over 500 meters, providing a good workout.

How many road cycling routes are available in the Cannondale area?

There are over 90 road cycling routes available around Cannondale, offering a wide selection for different preferences and skill levels. This includes a mix of easy, moderate, and difficult options.

Can I find routes that offer views of multiple reservoirs?

Absolutely. Many routes are designed to showcase the region's beautiful reservoirs. The View of Saugatuck Reservoir – View of Saugatuck Reservoir loop from Wilton, for example, provides extensive views of the Saugatuck Reservoir, a prominent feature of the landscape.

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