Whittemore Glen State Park
Whittemore Glen State Park
53
riders
29
rides
Road cycling in Whittemore Glen State Park features routes through extensive forested areas and rolling hills, offering views of the Naugatuck River Valley. The region includes the Larkin State Park Trail, a 10-mile crushed stone path suitable for road bikes that can handle unpaved surfaces. This area provides a serene environment with diverse flora and fauna, making it suitable for nature observation during rides.
Last updated: May 21, 2026
18
riders
47.4km
02:23
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
42.4km
02:08
560m
560m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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3
riders
27.7km
01:20
340m
340m
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.
7
riders
59.2km
02:38
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Whittemore Glen State Park
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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Whittemore Glen State Park offers over 20 road cycling routes, catering to various skill levels. You'll find a good mix of easy, moderate, and challenging options to explore the park's diverse landscapes.
The routes in Whittemore Glen State Park primarily feature extensive forested areas and rolling hills. You can also expect scenic views of the Naugatuck River Valley. The Larkin State Park Trail, a notable feature, is a 10-mile crushed stone path that is suitable for road bikes capable of handling unpaved surfaces.
Yes, Whittemore Glen State Park has a few easy road cycling routes. The Larkin State Park Trail, with its relatively flat and smooth crushed stone surface, is particularly well-suited for those seeking a less strenuous ride. While the guide primarily lists moderate routes, there are options for a more relaxed experience.
Parking is available at the entrances to Whittemore Glen State Park. For vehicles registered in Connecticut, parking is free through the Passport to the Parks program. Bike racks are also provided at the entrances for your convenience.
Among the popular routes, the Judd Hill Pond – Cox Nature Reserve loop from Waterbury-Oxford Airport is a favorite, covering 29.3 miles through rolling hills. Another highly regarded option is the Nichols Hill – Bald Hill loop from Waterbury, offering scenic views across the Naugatuck River Valley over 27.8 miles.
The park is beautiful throughout the warmer months, but autumn is particularly stunning. The vibrant fall foliage transforms the forested areas into a striking display of colors, creating a picturesque backdrop for your ride.
Yes, while many routes are moderate, Whittemore Glen State Park does offer a couple of more challenging road cycling routes. These typically feature greater elevation changes and longer distances, providing a good workout for experienced cyclists.
Absolutely. Whittemore Glen State Park is known for its diverse flora and fauna. As you cycle through forested lands and wetlands, you'll have opportunities for nature observation and bird watching. The Naugatuck River Valley also adds to the picturesque appeal.
Many of the road cycling routes in Whittemore Glen State Park are designed as loops, allowing you to start and finish at the same point. Examples include the Caleb Hill – Cox Nature Reserve loop from Waterbury-Oxford Airport and the Hesseky Meadow Pond – Radey Pond loop from Towantic Hill.
Road cycling in Whittemore Glen State Park is unique due to its blend of serene forested areas, rolling hills, and the distinctive Larkin State Park Trail. It offers a peaceful environment with opportunities for nature observation, making it a refreshing escape for cyclists.
The duration of road cycling routes in Whittemore Glen State Park varies. For instance, a route like the Bedlam Hill – Fenn Pond loop from Waterbury-Oxford Airport can be completed in about 1 hour 10 minutes, while longer routes like the Judd Hill Pond – Cox Nature Reserve loop might take around 2 hours 20 minutes.


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