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Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Sherman

The best road cycling routes around Sherman

5.0

(1)

76

riders

14

rides

Road cycling routes around Sherman offer diverse landscapes, from the flat to gently rolling terrain around Lake Texoma to the scenic routes near Hagerman National Wildlife Refuge. The region features a mix of open country, wetlands, and forests, providing varied backdrops for rides. Sherman's parks and surrounding areas contribute to a network of paths suitable for road cyclists seeking engaging outdoor experiences.

Best road cycling routes around Sherman

  • The most popular road cycling route is Squantz Pond – Squantz Pond…

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

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

Moderate
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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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Near and artist commune

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Wonderful food and rest stop at the end of the trail

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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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Jamie S.
January 17, 2024, King Hill Road

The top of King Hill Road (King Hill) stands at 574 feet, making for a challenging climb in a pretty area in Sharon, Connecticut.

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Frequently Asked Questions

How many road cycling routes are available around Sherman?

Komoot offers over a dozen road cycling routes around Sherman, catering to various skill levels. Most of these routes are classified as moderate, with a few more challenging options for experienced cyclists.

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

Road cycling around Sherman features a mix of flat to gently rolling terrain. You'll find scenic routes along Lake Texoma, offering expansive water views, and paths near natural preserves like Hagerman National Wildlife Refuge, which provide a peaceful, picturesque backdrop of wetlands, forests, and open country.

Are there any longer, more challenging road cycling routes in the Sherman area?

Yes, for those seeking a significant challenge, routes like Lake Warmaug State Park – Lake Waramaug loop from New Milford offer a difficult rating with substantial elevation gain over nearly 90 kilometers. This route is designed for experienced cyclists looking for a demanding ride.

What do other road cyclists say about the routes in Sherman?

The road cycling routes in Sherman are highly regarded by the komoot community, holding an average rating of 5.0 stars. Cyclists often praise the varied terrain and scenic beauty, particularly the peaceful stretches near natural areas.

Are there any road cycling routes suitable for a moderate ride with varied landscapes?

Absolutely. A popular choice for a balanced ride with varied terrain and moderate climbs is the Fife 'n Drum Restaurant & Inn loop from Sherman. This route covers approximately 59 kilometers and offers a diverse cycling experience.

Where can I find a good starting point for a road cycling route with significant elevation?

For a route with notable elevation gain, consider starting a loop like Squantz Pond – Squantz Pond loop from Candlewood Mountain. This route, approximately 56.5 kilometers long, features a moderate difficulty with significant ascents, making it a good option for those looking to challenge themselves.

Are there any shorter road cycling routes for a quicker ride near Sherman?

Yes, for a shorter ride, the Hatch Pond – Leonard Pond loop from Sherman is a great option. This moderate route is about 36.7 kilometers long, offering a quicker yet engaging cycling experience.

What are some natural attractions or points of interest I might see while road cycling near Sherman?

While road cycling near Sherman, you can enjoy views of Lake Texoma and the scenic areas surrounding Hagerman National Wildlife Refuge, known for its diverse wildlife and migratory birds. Herman Baker Park, with its picturesque Pickens Lake, also offers a serene setting that can be part of or a starting point for rides.

Is it possible to find road cycling routes that are loops around Sherman?

Many of the road cycling routes available around Sherman are designed as loops, allowing you to start and end your ride at the same point. Examples include the Fife 'n Drum Restaurant & Inn loop from Sherman and the Squantz Pond – Squantz Pond loop from Candlewood Mountain.

What is the best time of year for road cycling in the Sherman area?

Based on local cycling community insights, spring and fall generally offer the most pleasant weather for road cycling in Grayson County, Texas, providing cooler temperatures and less humidity compared to the summer months. Always check local weather conditions before heading out.

Are there any community-created cycling routes around Sherman that I can explore?

Yes, the active cycling community around Sherman has created various routes available on platforms like Bikemap. These include options such as the 'TBW Pottsboro 25 Loop' and the '26.5 Mile North Loop', showcasing established paths with varied distances and elevation changes suitable for road cycling.

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