5.0
(12)
306
riders
49
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.
Last updated: July 2, 2026
18
riders
47.4km
02:23
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
56.1km
03:02
820m
820m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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2
riders
42.4km
02:08
560m
560m
The Sherman Hill – Quassy loop from Waterbury offers a dynamic road cycling experience, blending paved roads with sections of hard-packed dirt and gravel. You'll navigate rolling hills and open…
3
riders
42.6km
02:10
590m
590m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
22.5km
01:10
320m
320m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Hiking around Bedlam Hill provides a serene experience amidst quiet residential surroundings. Although it's designated as a summit at 801 feet high, don't anticipate panoramic views. Instead, enjoy the surroundings as you immerse yourself in the tranquil ambiance of the area. Ideal for those seeking a leisurely hike in a calm environment.
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Cycling by Bedlam Hill offers a peaceful ride through a quiet residential area. Despite its status as a summit, reaching 801 feet high, there are no elevated views. Instead, enjoy the tranquil surroundings as you pedal along the paved roads. Ideal for those seeking a serene biking experience.
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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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Located in Litchfield, Judd Hill Pond is a small, yet idyllic lake, known for fishing near The Crossings nature reserve.
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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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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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There are over 50 road cycling routes available around Naugatuck, offering a variety of options for different skill levels and preferences.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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