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Routes
Cycling routes
United States
Connecticut
Northwest Hills Planning Region

Chimney Point

The best cycling routes around Chimney Point

4.8

(7)

8

riders

3

rides

Touring cycling around Chimney Point offers routes along the eastern shore of Lake Champlain, characterized by a blend of historical sites and scenic landscapes. The region features peaceful country roads, picturesque villages, and varied terrain, including flat, well-paved sections and more challenging segments with elevation changes. Cyclists can enjoy views of Lake Champlain and the distant Adirondack Mountains. The area is integrated into extensive cycling networks, providing diverse options for exploration.

Best touring cycling routes around Chimney Point

  • The most…

Last updated: June 29, 2026

4.7

(3)

1

riders

#1.

Whalen Pond loop from Brookfield Center

24.9km

01:38

300m

300m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

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Popular around Chimney Point

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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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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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Caro "Bandit"
February 24, 2022, Bulls Bridge

This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.

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church in the wild.

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Frequently Asked Questions

How many touring cycling routes are available around Chimney Point?

While komoot currently lists a few specific routes, Chimney Point is a central part of the extensive Lake Champlain Bikeways network, which offers over 1,600 miles of routes. This includes 35 loops and tours ranging from 10 to 60 miles, as well as the 363-mile Champlain Bikeway that encircles the entire lake, providing numerous options for exploration.

What is the typical terrain like for touring cycling in Chimney Point?

The Champlain Valley around Chimney Point features varied terrain. You'll find peaceful country roads with mostly well-paved, flat surfaces suitable for all fitness levels, especially along the lake. However, there are also more challenging segments with elevation changes for experienced riders, particularly on routes like Leonard Pond – Hatch Pond loop from Sherman.

Are there any family-friendly touring cycling options in the area?

Yes, the region offers many peaceful country roads and relatively flat sections, especially those integrated into the Lake Champlain Bikeways network, which are suitable for families. These routes often pass through picturesque villages and offer scenic views without excessive difficulty.

What are some scenic highlights or landmarks I can see while cycling?

Cyclists can enjoy stunning, serene views of Lake Champlain and the distant Adirondack Mountains. A significant landmark is the Chimney Point State Historic Site, which explores 9,000 years of human habitation. You can also cross the bicycle-friendly Lake Champlain Bridge to access the Crown Point State Historic Site on the New York side, featuring historic fort ruins.

Is the Lake Champlain Bridge accessible for cyclists?

Yes, the Lake Champlain Bridge, connecting Chimney Point, Vermont, to Crown Point, New York, is explicitly bicycle-friendly. It includes sidewalks and special lanes for cyclists, making it easy to cross and access additional routes and historic sites on the New York side.

What is the best time of year to go touring cycling in Chimney Point?

The best time for touring cycling in Chimney Point is generally from spring through fall when the weather is mild and the scenery is vibrant. The region offers beautiful foliage in autumn. While some routes may be accessible in winter, conditions can be challenging due to snow and ice.

Are there any longer, more challenging touring routes for experienced cyclists?

Yes, for experienced cyclists seeking a challenge, routes like the Leonard Pond – Hatch Pond loop from Sherman offer a difficult 37.1-mile path with significant elevation changes. The broader Lake Champlain Bikeways network also includes longer tours, such as the 363-mile Champlain Bikeway around the entire lake.

Can I find circular touring cycling routes around Chimney Point?

Yes, the Lake Champlain Bikeways network, which Chimney Point is part of, specifically boasts 35 loops and tours. For example, the Whalen Pond loop from Brookfield Center is a moderate 15.5-mile circular route, and the Bulls Bridge – Birch Hill loop from Sherman is a 24.1-mile option.

What do other touring cyclists say about the routes in Chimney Point?

The touring cycling routes around Chimney Point are highly rated by the komoot community, with an average score of 4.8 stars from over 4 reviews. Cyclists often praise the serene lake views, gentle country roads, and the varied terrain that caters to different ability levels.

Are there opportunities for wildlife viewing while cycling?

Yes, the natural landscapes around Chimney Point, particularly near Lake Champlain, offer opportunities for wildlife viewing. The Chimney Point State Historic Site is noted as a good location for birdwatching, especially in late fall and winter, where various duck species can be observed.

Is there parking available near the touring cycling routes?

Parking is generally available at key access points for the Lake Champlain Bikeways network and at attractions like the Chimney Point State Historic Site. It's advisable to check specific starting points for designated parking areas before your ride.

Are there any touring routes that offer significant elevation changes for a challenge?

Absolutely. For those seeking more challenging climbs, routes like the Observatory Hill – Seeley Hill loop from New Fairfield, a difficult 30.1-mile route, feature substantial elevation gains, providing a rewarding workout amidst scenic views.

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