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Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Lakeside Woods

The best road cycling routes around Lakeside Woods

75

riders

12

rides

Road cycling around Lakeside Woods features a landscape characterized by rolling hills and forested areas, offering varied terrain for cyclists. The region includes several lakes, providing scenic backdrops for routes that navigate through the countryside. Road cyclists can expect elevation changes throughout the area, with routes ranging from moderate climbs to more challenging ascents.

Best road cycling routes around Lakeside Woods

  • The most popular road cycling route is Squantz Pond – Squantz Pond loop from Candlewood Mountain, a 35.1…

Last updated: July 12, 2026

8

riders

#1.

Squantz Pond – Squantz Pond loop from Candlewood Mountain

56.5km

02:50

790m

790m

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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Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

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

Easy

4

riders

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Popular around Lakeside Woods

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Cycling around Lakeside Woods

Tips from the Community

Zachary
September 3, 2024, Lake Waramaug State Park

This is a tiny but highly scenic little park. The roads that circumnavigate Lake Warmaug are partially shaded and go right up to the water's edge, and the views out across the water are especially beautiful in the autumn. There is also camping, hiking, and kayaking here, as well as a couple small beaches for swimming.

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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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This small lake-side park comes equipped with picnic benches and plenty of trees to provide shade on a summers day. A great spot to take a break.

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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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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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Cemetery at the beginning of the decent. Watch out, there is a sharp turn in the middle of the segment.

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Frequently Asked Questions

What kind of terrain can I expect when road cycling around Lakeside Woods?

Road cycling around Lakeside Woods is characterized by rolling hills and forested areas, offering varied terrain. You can expect elevation changes throughout the area, with routes ranging from moderate climbs to more challenging ascents. The region also includes several lakes, providing scenic backdrops for your rides.

Are there road cycling routes suitable for different skill levels in Lakeside Woods?

Yes, the road cycling network around Lakeside Woods offers options for various ability levels. While there are no routes specifically graded as 'easy' in our current selection, you'll find 9 moderate routes and 2 difficult routes, ensuring options for both intermediate and experienced cyclists.

What are some popular loop routes for road cycling in Lakeside Woods?

Many road cycling routes in Lakeside Woods are designed as loops, offering a comprehensive tour of the area. A popular choice is the Squantz Pond – Squantz Pond loop from Candlewood Mountain, which covers 35.1 miles (56.5 km) with significant elevation gain. Another favorite is the Fife 'n Drum Restaurant & Inn loop from Sherman, a moderate 36.7-mile (59.1 km) path with a mix of forested sections and open roads.

What are the typical lengths and durations for road cycling routes in Lakeside Woods?

The road cycling routes in Lakeside Woods vary in length and duration. For example, the Hatch Pond – Leonard Pond loop from Sherman is about 22.8 miles (36.7 km) and takes around 1 hour 39 minutes. Longer routes, like the challenging Lake Warmaug State Park – Lake Waramaug loop from New Milford, span 55.6 miles (89.5 km) and can take nearly 5 hours to complete.

What natural features or landmarks can I see along the road cycling routes?

While the specific road cycling routes primarily focus on scenic roads, the broader Lakeside Woods area offers several natural attractions. You might pass by areas near Squantz Pond State Park or Squantz Pond itself. The region is known for its wooded landscapes, and you may encounter viewpoints like the River Trail or forested areas such as Harrybrooke Park.

Is Lakeside Woods suitable for family-friendly road cycling?

The road cycling routes in Lakeside Woods are generally characterized by rolling hills and elevation changes, with routes graded as moderate to difficult. While the region is beautiful, the specific wilderness areas often described as 'Lakeside Woods' are more geared towards hiking and mountain biking on rugged trails. For road cycling, families might prefer exploring paved roads in surrounding towns or designated paved paths outside these specific wilderness areas, as the listed routes involve significant distances and elevation.

What is the best time of year for road biking in Lakeside Woods?

The best time for road biking in Lakeside Woods is typically during the spring, summer, and fall months when the weather is milder and the scenery is vibrant. The region's forested areas are particularly beautiful during autumn. Winter conditions can bring snow and ice, making road cycling more challenging or unsafe on many routes.

Are there any specific parking recommendations for accessing road cycling routes?

While specific parking details for each route start point are best checked on the individual komoot tour pages, many routes around Lakeside Woods begin from towns or established parks. For example, routes like the Squantz Pond loop start from areas like Candlewood Mountain, where public parking may be available. Always verify parking availability and regulations before your ride.

Can I find cafes or other amenities along the road cycling routes in Lakeside Woods?

Many road cycling routes in Lakeside Woods pass through or near small towns and communities, where you can typically find cafes, restaurants, and other amenities. For instance, the Fife 'n Drum Restaurant & Inn loop from Sherman suggests a starting point that implies access to local establishments. Planning your route with komoot allows you to identify points of interest and services along the way.

What do other road cyclists enjoy most about road cycling in Lakeside Woods?

Road cyclists using komoot to explore Lakeside Woods often praise the varied terrain, which includes rolling hills and forested roads, and the scenic lakeside views. The region offers a good mix of moderate and difficult routes, appealing to those looking for a challenging yet rewarding ride through natural landscapes.

Are there any specific considerations for road cycling in Lakeside Woods during winter?

During winter, road cycling in Lakeside Woods can be significantly impacted by weather conditions. Snow and ice can make roads hazardous, especially in hilly and forested areas. It's advisable to check local weather forecasts and road conditions before planning a winter ride. Many cyclists opt for indoor training or other sports during the colder months.

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