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Routes
Road cycling routes
United States
Connecticut
Northwest Hills Planning Region

Chimney Point

The best road cycling routes around Chimney Point

4.0

(1)

45

riders

12

rides

Road cycling routes around Chimney Point offer diverse terrain with views of Lake Champlain and the Adirondack Mountains. The region features a mix of paved roads and some sections with hard-packed dirt or gravel, characterized by rolling climbs and winding descents. The landscape includes rural scenery, farms, orchards, and forests, providing varied backdrops for cycling.

Best road cycling routes around Chimney Point

  • The most popular road cycling route is Squantz Pond – Bulls Bridge loop from New Fairfield, a…

Last updated: May 17, 2026

4.0

(1)

4

riders

#1.

Harrybrooke Park loop from Brookfield

31.0km

01:37

340m

340m

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

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Moderate

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 Chimney Point

Hiking around Chimney Point

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Gravel biking around Chimney Point

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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church in the wild.

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Frequently Asked Questions

How many road cycling routes are available around Chimney Point?

There are over 10 road cycling routes around Chimney Point, offering a variety of experiences. These include options ranging from moderate to difficult, with a few easier routes also available.

What kind of terrain can I expect on road cycling routes in Chimney Point?

Road cycling routes in Chimney Point feature diverse terrain, including rolling climbs and winding descents. While mostly paved, some sections may include hard-packed dirt or gravel roads. You'll be treated to views of Lake Champlain, the Adirondack Mountains, and charming rural scenery with farms, orchards, and forests.

Are there routes suitable for beginners or less experienced cyclists?

Yes, there are easier options available. For instance, the 'roadbike loop from Button Bay State Park' is well-suited for any fitness level due to its mostly well-paved and easy-to-ride surfaces. While not explicitly listed in the routes data, the region generally offers routes for varying abilities.

What are some challenging road cycling options in the area?

For a challenging ride with significant elevation gain, consider the Squantz Pond – Bulls Bridge loop from New Fairfield. This 54.7-mile (88.0 km) route takes over 4 hours to complete and features over 1000 meters of ascent.

Can I find long-distance road cycling routes around Chimney Point?

Yes, Chimney Point is part of the broader Lake Champlain Bikeway, a massive 363-mile cycling route that encircles Lake Champlain. This system also includes 992 miles of themed loop rides, primarily on paved roads with minimal traffic, offering excellent conditions for long-distance touring.

What historical sites or natural landmarks can I see while cycling?

You can explore several significant sites. The Chimney Point State Historic Site itself offers a rich historical context. Cycling across the Lake Champlain Bridge provides remarkable views and connects you to the Crown Point State Historic Site in New York, featuring preserved fort ruins. Many routes also offer breathtaking vistas of Lake Champlain and the Adirondack Mountains.

Are there any family-friendly cycling options?

While specific family-friendly routes are not detailed in the provided data, the 'roadbike loop from Button Bay State Park' is described as easy and suitable for any fitness level, making it a good option for families. Button Bay State Park also offers camping, swimming, and other activities.

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

The region's natural beauty, including farms, orchards, and forests, suggests that late spring, summer, and early fall would be ideal for road cycling, offering pleasant weather and vibrant scenery. Always check local weather conditions before your ride.

Where are good starting points for road cycling routes in Chimney Point?

Many routes can be started from various points around Chimney Point. The Chimney Point State Historic Site offers picnic areas and a boat launch, which could serve as a convenient starting point. Button Bay State Park is another excellent option, especially for the easier loop mentioned.

Are there scenic routes with opportunities for breaks or refreshments?

Yes, many routes offer scenic views of Lake Champlain and the Adirondacks. While specific cafes aren't listed, the rural landscape often includes charming towns where you might find local establishments. The Chimney Point State Historic Site itself has a tavern building (circa 1785) and picnic areas for breaks.

What do other cyclists say about the road cycling experience in Chimney Point?

The road cycling routes in Chimney Point are highly rated by the komoot community, with an average score of 4.0 stars from over 1 review. Cyclists often praise the diverse terrain, stunning lake and mountain views, and the deep historical roots of the area.

Is it possible to combine cycling with other activities in the area?

Absolutely! Beyond cycling, Chimney Point and its surroundings offer ample opportunities for other outdoor pursuits. The Lake Champlain narrows are popular for anglers, and a boat launch provides lake access. Birdwatching is also popular, and nearby Button Bay State Park offers camping, swimming, fishing, and hiking.

How can I explore routes that cross Lake Champlain?

You can explore routes that traverse both sides of Lake Champlain by utilizing the Lake Champlain Bridge, which connects Chimney Point in Vermont with Crown Point in New York and offers pedestrian and bicycle access. Some routes also include crossing the lake via ferry to Ticonderoga, New York, adding an interesting element to your ride.

Most popular routes around Chimney Point

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