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Road cycling routes
United States
Connecticut
South Central Connecticut Planning Region

Naugatuck

The best road cycling routes around Naugatuck

4.8

(17)

336

riders

56

rides

Road cycling around Naugatuck, Connecticut, features a landscape characterized by rolling hills, numerous ponds, and the presence of the Housatonic River. The region offers varied terrain suitable for road cyclists, including routes that pass through natural reserves and local parks. Elevations are generally moderate, with some routes incorporating climbs up to several hundred meters. The area's geography provides a mix of open roads and tree-lined sections.

Best road cycling routes around Naugatuck

  • The most popular road cycling route is Granite…

Last updated: October 5, 2026

22

riders

#1.

View of Long Meadow Pond – East Spring Brook loop from Post University

53.1km

02:48

810m

810m

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

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Moderate

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

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Tips from the Community

Jamie S.
February 25, 2024, Middlebury Greenway (Chase Road Section)

This section of the Middlebury Greenway near Chase Road is an especially scenic bit of riding on this popular, paved multi-use path. You ride on the raised trail above a pretty stream, then pass through an interesting rock notch east of Chase Road. This is a great bit of riding that is also away from cars.

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Jamie S.
February 25, 2024, Fenn Pond

Fenn Pond is a small freshwater pond between Middlebury Avenue and Charcoal Road. This attractive body of water is in an open field and surrounded by reeds, making it a peaceful spot to ride past.

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oliviakellis
February 24, 2024, Judd Hill Pond

Located in Litchfield, Judd Hill Pond is a small, yet idyllic lake, known for fishing near The Crossings nature reserve.

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Jamie S.
February 24, 2024, Sherman Hill

Sherman Hill is a 604-foot hill on Old Sherman Hill Road in Woodbury. This is a nice little climb in a quiet residential area surrounded by forest and old stone walls.

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This historic home offers guided tours for a fee. The gardens are nice, especially in the spring with the flowers in bloom. The property also joins the 81-acre Bellamy Preserve.

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Long Meadow Pond stretches north from Bellamy Lane to the Schwartz Preserve. This preserve protects the north eastern section of lake, keeping it free from the development that surrounds the rest of the lake.

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This woodland just off Tuttle Road is a natural reserve of trees and land. There is no public access into the reserve, but you get a good feel for the natural beauty of the area when riding down the road.

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The Natalie White Preserve is one of many such preserves overseen by the Roxbury Land Trust. Though small there is a short trail leading to a hilltop that affords nice views of the areas and makes for a good picnic spot.

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Frequently Asked Questions

How many road cycling routes are available around Naugatuck?

There are over 50 road cycling routes available around Naugatuck, offering a variety of options for different skill levels and preferences.

Are there easy road cycling routes suitable for beginners in Naugatuck?

Yes, Naugatuck offers several easy road cycling routes. There are 13 routes specifically categorized as easy, perfect for those new to road cycling or looking for a more relaxed ride.

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

The terrain around Naugatuck is characterized by rolling hills, numerous ponds, and sections along the Housatonic River. You'll find a mix of open roads and tree-lined areas, with moderate elevations and some climbs up to several hundred meters.

Are there any challenging road cycling routes for experienced riders?

Yes, for experienced riders seeking a challenge, Naugatuck has 2 routes categorized as difficult, alongside 40 moderate routes that often include significant climbs and longer distances. For example, the View of Housatonic River – Minor Bridge loop from Hidden Pond Park features over 800 meters of elevation gain.

Can I find road cycling routes that pass by scenic viewpoints or natural attractions?

Absolutely. Many routes offer scenic views. For instance, the popular Granite Hill view – View of Sleeping Giant loop from Kathan Woods provides views of Granite Hill and the Sleeping Giant mountain range. You can also explore highlights like Gorge Cascade Falls or the serene Hop Brook Lake, which are near some cycling paths.

Are there any loop trails for road cycling in the Naugatuck area?

Yes, many of the road cycling routes around Naugatuck are designed as loops. Examples include the Judd Hill Pond – Cox Nature Reserve loop from Waterbury-Oxford Airport and the Cedarland Park – Radey Pond loop from Hidden Pond Park, offering convenient circular rides.

What do other road cyclists say about the routes in Naugatuck?

The road cycling routes in Naugatuck are highly rated by the komoot community, with an average score of 4.7 stars from over 18 reviews. Cyclists often praise the varied terrain, scenic ponds, and routes along the Housatonic River.

Are there any bike-friendly cafes or places to stop for refreshments along the routes?

While specific cafes directly on every route aren't listed, you can find options like Fussy Coffee at Science Park in the broader Naugatuck area, which is a popular stop for many. Planning your route with komoot can help you identify other potential stops.

What is the typical duration for road cycling routes in Naugatuck?

Route durations vary significantly based on distance and elevation. For example, the Granite Hill view – View of Sleeping Giant loop typically takes around 2 hours 5 minutes, while the Quassy – Caleb Hill loop from Middlebury might take closer to 2 hours 30 minutes for an average rider.

Are there any routes that pass by lakes or ponds?

Yes, the Naugatuck region is known for its numerous ponds and lakes. Routes like the Judd Hill Pond – Cox Nature Reserve loop traverse areas around Judd Hill Pond. You can also find highlights such as Hop Brook Lake and Lake Bethany Dam near various cycling paths.

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

Spring, summer, and fall generally offer the best conditions for road cycling in Naugatuck. Spring brings blooming scenery, summer provides warm weather, and fall showcases vibrant foliage. Always check local weather forecasts before heading out, especially for rain or strong winds.

Are there any routes that follow dedicated cycle paths or trails?

While many routes are on roads, you can find sections of dedicated paths. For instance, a section of the Farmington Canal Heritage Trail is accessible in the wider Naugatuck area, offering a car-free cycling experience.

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Browse the best Road cycling routes in other regions.

New HavenEast HavenWaterburyCheshire VillageUniversité QuinnipiacSleeping Giant State ParkNaugatuck State ForestWolcott Recreation AreaNorth HavenFarmington Canal Line State Park TrailMeridenWest HavenWoodmontWest Rock Ridge State ParkFarm River State ParkDerbyMilford City (Balance)OrangeHammonasset Beach State ParkNaugatuck State Forest -East BlockMadison CenterSouthford Falls State ParkGuilford CenterQuinnipiac River State ParkHeritage VillageGeorge C. Waldo State ParkBranford CenterAnsoniaNorthfordWhittemore Glen State ParkNaugatuck State Forest - Quillinan Reservoir BlockWallingford CenterOsbornedale State Park

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