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.
Last updated: July 12, 2026
8
riders
56.5km
02:50
790m
790m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
59.1km
02:36
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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7
riders
89.5km
04:54
1,620m
1,620m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
8
riders
35.1km
01:29
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
19.0km
00:55
210m
210m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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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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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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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