5.0
(22)
442
riders
19
rides
No traffic road cycling routes in Naugatuck State Forest traverse a landscape characterized by wild woodlands, the Naugatuck River valley, and gentle hills. The region features a mix of undeveloped forests, grasslands, and rivers, with some areas offering dedicated greenways. While the forest itself contains "woods roads" more suited for mountain biking, the surrounding area provides paved paths and firm, unpaved surfaces ideal for road cycling. These routes offer varied terrain through scenic river valleys and diverse natural settings.
Last updated: May 25, 2026
5.0
(4)
60
riders
29.5km
01:10
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
24
riders
49.8km
02:14
340m
340m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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5.0
(1)
9
riders
16.6km
00:39
20m
20m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5
riders
38.8km
01:57
480m
480m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
3
riders
27.7km
01:20
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Naugatuck State Forest
The Milton Train Depot was built in 1882 and remains today as a refurbished, one-room station.
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Has baked good but also a sit down place to eat brunch. Really good!
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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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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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Located in Litchfield, Judd Hill Pond is a small, yet idyllic lake, known for fishing near The Crossings nature reserve.
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There are over 20 traffic-free road cycling routes available in and around Naugatuck State Forest, offering a variety of distances and experiences. You can find routes ranging from easy to moderate difficulty.
Yes, many routes are suitable for beginners. For example, the Cran Preserve – Milton Train Depot loop from Lock 12 Historical Park is an easy route covering just over 21 km with minimal elevation gain, perfect for a relaxed ride.
The routes often traverse wild woodlands, open grasslands, and areas near rivers and lakes within the scenic Naugatuck River valley. You might encounter dramatic rock formations, streams, and historical stone fences. While the forest itself has many unpaved 'woods roads', the designated traffic-free routes often follow adjacent greenways or quiet country lanes, offering views of the diverse landscape.
While the forest's interior features overlooks like those in the West Block of Naugatuck State Forest, many traffic-free road cycling routes in the broader area, such as the Granite Hill view – View of Sleeping Giant loop from Cheshire, offer scenic vistas and expansive views of the surrounding region.
Yes, several easy routes are ideal for families. The low elevation gain and traffic-free nature of many paths make them safe and enjoyable for all ages. Look for routes marked as 'easy' in the guide, such as the Cran Preserve loop from Cheshire, which is just over 16 km long.
Generally, dogs are welcome on trails and paths in Naugatuck State Forest and many adjacent greenways, provided they are kept on a leash. However, specific rules can vary by trail or park section, so it's always best to check local signage or official park websites for the most current regulations before you go.
Parking is typically available at various access points for the greenways and state park trails that host these traffic-free routes. For example, routes starting near Cheshire or Lock 12 Historical Park often have designated parking areas. Always check the specific route details on komoot for recommended starting points and parking information.
Spring, summer, and fall generally offer the best conditions for road cycling. Spring brings lush greenery, while autumn showcases vibrant fall foliage, making for particularly scenic rides. Summer is also great, but be mindful of warmer temperatures. Winter cycling is possible but depends on snow and ice conditions, as some paths may not be cleared.
The komoot community highly rates the cycling experience in this area, with an average score of 4.9 stars. Reviewers often praise the peacefulness of the routes, the beautiful natural surroundings, and the joy of riding away from vehicle traffic.
Yes, many of the traffic-free road cycling routes in this guide are designed as loops, allowing you to start and end at the same point without retracing your steps. An example is the Milton Train Depot – Paul Gregory’s Bistro loop from Cheshire, which offers a pleasant circular ride.
This guide focuses on road cycling, so the routes primarily utilize paved surfaces or very well-maintained, firm unpaved paths suitable for road bikes, such as those found on dedicated greenways like the Naugatuck River Greenway or sections of the Larkin State Park Trail. While Naugatuck State Forest itself has many unpaved 'woods roads', the selected routes aim for traffic-free surfaces suitable for road bikes.
While many routes are easy, there are moderate options available for those seeking more of a challenge. For instance, the Caleb Hill – Cox Nature Reserve loop from Waterbury-Oxford Airport is a moderate route covering over 27 km with significant elevation gain, offering a more demanding ride.


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