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Routes
Road cycling routes
United States
Connecticut
South Central Connecticut Planning Region

Naugatuck State Forest

The best road cycling routes in Naugatuck State Forest

4.9

(58)

757

riders

71

rides

Road cycling in Naugatuck State Forest offers diverse terrain across nearly 5,000 acres of Connecticut woodlands. The region features an irregular landscape of rolling hills, steep-sided valleys, and low-lying swamps, shaped by glacial erosion. Numerous rivers and reservoirs, including the Naugatuck River, provide scenic backdrops for road cycling routes. The forest's mix of evergreen and hardwood woods, along with wider woods roads and nearby multi-use greenways, provides varied conditions for cyclists.

Best road cycling routes in Naugatuck State Forest

  • The…

Last updated: May 4, 2026

2

riders

#1.

Hesseky Meadow Pond – Radey Pond loop from Towantic Hill

48.6km

02:18

560m

560m

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

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Moderate

5.0

(3)

59

riders

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

Easy
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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. Some segments of this route may be unpaved and difficult to ride.

Moderate

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 Naugatuck State Forest

Hiking in Naugatuck State Forest

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Cycling in Naugatuck State Forest

MTB Trails in Naugatuck State Forest

Tips from the Community

Garmin2017!
May 22, 2025, Farmington Canal Heritage Trail

Fun ride

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Go see it

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The Milton Train Depot was built in 1882 and remains today as a refurbished, one-room station.

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This trail runs about 84 miles in total from Northampton to New Haven. This section of the trail is well marked and paved but stops here around Lazy Lane.

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Lisa
February 25, 2024, View of Sleeping Giant

The obvious, tree-covered hill to your northeast, on the far side of the Mill River, is Sleeping Giant, which looks like the head of the giant when viewed from the right angle. You can also bike north or south from here on the Farmington Heritage Canal, which is part of the East Coast Greenway.

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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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From here you can see lovely views of Milford Harbor and the wetland around it.. Keep your eyes peeled for the varied bird species that inhabit the shoreline.

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Frequently Asked Questions

How many road cycling routes are available in Naugatuck State Forest?

Naugatuck State Forest offers a wide selection of road cycling routes, with over 70 options available. These routes cater to various skill levels, including 20 easy, over 50 moderate, and a few more challenging rides.

What kind of terrain can I expect when road cycling in Naugatuck State Forest?

The terrain in Naugatuck State Forest is quite diverse, featuring an irregular landscape of rolling hills, steep-sided valleys, and woodlands. You'll find a mix of wider 'woods roads' within the forest and nearby multi-use greenways, which often have smoother, firmly packed surfaces ideal for road cycling. Routes can range from gentle climbs along river valleys to more significant elevation gains through forested areas.

Are there any scenic viewpoints or natural features to see along the road cycling routes?

Yes, Naugatuck State Forest is rich in natural beauty. You can expect to see several reservoirs, rivers like the Naugatuck River, and even waterfalls such as Spruce Brook Falls and Roaring Brook Falls. Dramatic rock formations and overlooks like Beacon Cap or those offering views of the Naugatuck River Valley are also common. Some routes, like the Granite Hill view – View of Sleeping Giant loop from Kathan Woods, specifically highlight scenic viewpoints.

What are the typical surfaces like for road cycling in the area, especially on greenways?

While the forest itself features wider 'woods roads,' the surrounding region offers multi-use greenways and former railroad beds. These typically provide generally flat, paved, or firmly packed surfaces, making them excellent for road cycling. The Naugatuck River Greenway, for example, offers scenic views along the river on such surfaces, and the Larkin State Park Trail is known for its unpaved but firm path suitable for cycling.

Are there any family-friendly road cycling routes in Naugatuck State Forest?

Yes, there are several routes suitable for families. The forest offers options with milder terrain and gentle climbs. An excellent example is the Cran Preserve – Milton Train Depot loop from Lock 12 Historical Park, which is an easy 13.1-mile path with minimal elevation gain, perfect for a relaxed family outing.

What is the best time of year to go road cycling in Naugatuck State Forest?

The forest is beautiful year-round, but spring and fall are particularly popular. Spring brings lush greenery, while fall offers vibrant foliage displays, especially with the mix of evergreen and hardwood woods. Summer is also great, though it can be warmer. Winter cycling is possible, but conditions may vary depending on snow and ice, especially on unpaved sections.

Are there any loop trails for road cyclists?

Yes, many of the road cycling routes in Naugatuck State Forest are designed as loops, allowing you to start and end at the same point. For instance, the popular Hesseky Meadow Pond – Radey Pond loop from Towantic Hill is a 30.2-mile loop with significant elevation gain, offering a comprehensive tour of varied woodlands.

What do other road cyclists enjoy most about cycling in Naugatuck State Forest?

The area is highly rated by the komoot community, with an average score of 4.9 stars from more than 20 reviews. Cyclists often praise the diverse terrain, from challenging climbs to scenic riverside paths, and the opportunity to explore wild, undeveloped woodlands and historical sites. The variety of routes ensures there's something for every ability level.

Is there parking available for road cyclists visiting Naugatuck State Forest?

While specific parking areas for each route may vary, Naugatuck State Forest is accessible from several towns, and trailheads often have designated parking. It's advisable to check the starting point of your chosen route on komoot for detailed parking information.

Can I bring my dog along on road cycling routes?

While Naugatuck State Forest is generally dog-friendly for hiking, road cycling with a dog directly on the bike can be challenging and is typically not recommended for safety reasons. However, if you're cycling on wider woods roads or multi-use paths, and your dog is well-behaved and on a leash, they might be able to accompany you alongside the path, where permitted. Always ensure your dog's safety and comfort, and check local regulations regarding pets on specific trails.

Are there any historical sites to explore along the routes?

Yes, Naugatuck State Forest has a rich history. You can find remnants of 18th-century ironworks ruins, abandoned homes, and old stone fences from former farms within the forest. These historical elements add an interesting dimension to your ride, offering glimpses into the region's past as you cycle through the natural landscape.

Are there any very long road cycling routes for endurance training?

For those seeking longer rides, Naugatuck State Forest and its surrounding areas offer routes that extend for significant distances. For example, the Silver Sands State Park Beach – View on the harbour of Milford loop from Seymour covers over 58 miles (93 km) with substantial elevation gain, providing a challenging option for endurance cyclists.

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