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Routes
Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Bogus Hill

The best road cycling routes around Bogus Hill

4.0

(1)

48

riders

15

rides

Road cycling routes around Bogus Hill are characterized by varied terrain, including rolling hills and stretches through rural landscapes. The area features a mix of open roads and tree-lined sections, providing diverse cycling experiences. Elevations vary, with some routes offering moderate climbs and descents. The region's geography supports both shorter, less strenuous rides and longer, more challenging excursions.

Best road cycling routes around Bogus Hill

  • The most popular road cycling route is Maybrook Trailway – Whaley Lake loop from Putnam…

Last updated: June 29, 2026

9

riders

#1.

Fife 'n Drum Restaurant & Inn loop from Sherman

59.1km

02:36

550m

550m

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

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Moderate

4.0

(1)

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy 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. Some segments of this route may be unpaved and difficult to ride.

Moderate

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

Easy
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Popular around Bogus Hill

Hiking around Bogus Hill

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Cycling around Bogus Hill

Tips from the Community

Zachary
September 26, 2024, View of the Housatonic River

This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.

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Andrus
February 25, 2024, Harrybrooke Park

Harrybrooke Park is a hidden gem in an ideal setting near the river. In addition to the lovely surroundings the the Historic Harden House Museum is open to visitors.

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Matthew
February 20, 2024, Disbrow Pond

Disbrow Pond is a small body of water just off the side of Sawmill Road. You get a pretty great view from the bridge crossing over the water, but you can hop off the bike and go down next to the water if you pull into the entrance on the north side of the reservoir.

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Jamie S.
February 20, 2024, Squantz Pond

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

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Jamie S.
February 14, 2024, Squantz Pond

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

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Douglas Nadig
September 26, 2021, Harrybrooke Park

on exit path from park.

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Opportunity to have a decent meal along this route. Friendly folks refill water and it has a proper washroom as well. In general Kent is a good stop to refill or rest before heading further as supply station might become sparse.

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Frequently Asked Questions

How many road cycling routes are available around Bogus Hill?

There are 16 road cycling routes around Bogus Hill, offering a variety of experiences. These include 2 easy routes, 13 moderate routes, and 1 difficult route, catering to different skill levels.

What kind of terrain can I expect on road cycling routes near Bogus Hill?

Road cycling routes around Bogus Hill feature varied terrain, including rolling hills and stretches through rural landscapes. You'll find a mix of open roads and tree-lined sections, with elevations varying to provide both moderate climbs and descents, as well as longer, more challenging excursions.

Are there any challenging road cycling climbs in the Bogus Hill area?

Yes, the region offers routes with significant elevation gain. For instance, the Squantz Pond – Bulls Bridge loop from New Fairfield is a difficult 54.7-mile route with over 3,385 feet (1032 meters) of climbing, providing a substantial challenge for advanced cyclists.

What are some popular loop routes for road cycling around Bogus Hill?

Many cyclists enjoy loop routes in the area. Two popular options are the Maybrook Trailway – Whaley Lake loop from Putnam Lake, a moderate 36.6-mile ride, and the Fife 'n Drum Restaurant & Inn loop from Sherman, which is also a moderate 36.7-mile path.

Are there any family-friendly road cycling options near Bogus Hill?

While the guide primarily features moderate to difficult routes, there are 2 easy routes available that could be suitable for families or those looking for a less strenuous ride. These routes offer gentler terrain and shorter distances, perfect for a relaxed outing.

What do other road cyclists think about the routes in Bogus Hill?

The road cycling routes in Bogus Hill are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the varied terrain, scenic countryside, and the options available for different ability levels.

What attractions can I see along the road cycling routes around Bogus Hill?

While cycling, you can explore natural attractions such as Squantz Pond State Park and Squantz Pond itself. You might also pass by Harrybrooke Park, offering a pleasant natural setting.

Are there any hidden gem road cycling trails near Bogus Hill?

For those looking for less-traveled paths, the area offers numerous routes that wind through quiet rural landscapes. Consider exploring routes like the Hatch Pond – Leonard Pond loop from Sherman, which provides a moderate 22.8-mile ride through scenic countryside, away from busier roads.

What is the best time of year for road biking around Bogus Hill?

The best time for road biking around Bogus Hill is generally during the warmer months when the roads are clear and the weather is pleasant. The region's lush green landscapes are particularly beautiful in July and August, often with wildflowers in bloom, enhancing the scenic experience.

Are there any routes that offer scenic viewpoints around Bogus Hill?

Many routes in the Bogus Hill area provide scenic vistas as they traverse rolling hills and open countryside. While specific viewpoints are not detailed for every route, the varied elevation changes and rural settings ensure plenty of picturesque moments, especially on routes that pass by lakes or through forested sections.

How long are the road cycling trails near Bogus Hill?

The road cycling trails near Bogus Hill vary in length. You can find shorter, less strenuous rides, as well as longer, more challenging excursions. For example, the Harrybrooke Park loop from Brookfield is a moderate 19.2-mile route, while the Squantz Pond – Bulls Bridge loop from New Fairfield extends to 54.7 miles.

Most popular routes around Bogus Hill

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