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Routes
Gravel rides
United States
Connecticut
Northeastern Connecticut Planning Region

South Windham

The best gravel rides around South Windham

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riders

5

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Gravel biking around South Windham, Maine, offers a diverse landscape characterized by riverine paths, forested preserves, and varied terrain. The region features a network of trails that include hard-packed gravel sections, paved rail trail segments, and dirt woods trails. These routes often follow the Saco and Presumpscot Rivers, providing scenic views and connecting communities. The topography includes gentle slopes and some more challenging sections through forests, making it suitable for different gravel biking experiences.

Best gravel bike trails around South Windham

  • The most popular gravel bike trail is James L. Goodwin State Forest loop from Two Sister's Preserve, a 25.4 miles (40.9 km) trail that takes 2 hours 35 minutes to complete. This moderate route features varied terrain through forested areas.
  • Another top favourite among local gravel bikers is Air Line State Park trail – Air Line Trail loop from Willimantic, a moderate 26.1 miles (42.0 km) path. This route follows an abandoned rail line, offering a mix of surfaces.
  • Local gravel bikers also love the East Coast Greenway – James L. Goodwin State Forest loop from Willimantic, a 21.9 miles (35.3 km) trail leading through diverse forests and along river corridors, often completed in about 2 hours 27 minutes.
  • Gravel biking around South Windham is defined by riverine paths, extensive forest preserves, and former rail corridors, with options for both easy and more challenging routes. The network offers options for different ability levels, from compact gravel paths to dirt woods trails.
  • The routes in South Windham are highly rated by the komoot community with an average score of 5.0 stars from over 3 reviews. More than 30 gravel bikers have used komoot to explore South Windham's varied terrain.

Last updated: May 11, 2026

5

riders

#1.

James L. Goodwin State Forest loop from Two Sister's Preserve

40.9km

02:35

270m

270m

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

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Moderate

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

Moderate
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Easy gravel ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

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

Moderate

Easy gravel ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

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Popular around South Windham

Hiking around South Windham

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Cycling around South Windham

Tips from the Community

oliviakellis
August 4, 2024, Goodwin Heritage Trail & Natchaug Trail Junction

At the junction of the Airline Trail and Natchaug Trail in James L. Goodwin State Forest, hikers have two enticing options. Following the Natchaug Trail leads deeper into the forest, eventually reaching the serene Black Spruce Pond. Alternatively, continuing along the Airline Trail provides beautiful views of the 135-acre Pine Acres Lake. Both routes offer unique scenic experiences, showcasing the diverse beauty of the forest.

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Gateway to many gnarly mtb trails and the gravel/dirt roads of eastern CT

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The James L. Goodwin State Forest is a Connecticut state forest that spans around 2,000 acres. The land was donated by James L. Goodwin to the state in 1964. This forest can be seen along the East Coast Greenway near Pine Acres Lake.

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This park runs alongside the Willimantic River, providing scenic views of the water. On the opposite side, there are train tracks where you can occasionally observe interesting carts passing by.

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The Airline State Park Trail is divided into sections, and the northern section spans 21 miles from Windham to Putnam, making it a popular rail trail among hikers, runners, and bikers.

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The James L. Goodwin State Forest is a Connecticut state forest that spans around 2,000 acres. The land was donated by James L. Goodwin to the state in 1964. This forest can be seen along the East Coast Greenway near Pine Acres Lake.

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The Hop Park State Trail is part of the larger and expansive East Coast Trail. This section showcases stunning wooded areas and shaded pathways. This section is also fine for a road bike with thinner tires and a lightweight frame.

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On your ride along the Hop River State Park Trail, you'll spot the Andover Memorial Bridge spanning Hebron Road below. It's a special bridge, important to the area, offering a nice view of the surroundings.

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Frequently Asked Questions

How many gravel bike trails are available in South Windham?

South Windham offers a selection of 5 gravel bike routes, ranging from easy to moderate difficulty. These trails provide diverse experiences across riverine paths, forested preserves, and former rail corridors.

Are there any easy gravel biking routes suitable for beginners or families in South Windham?

Yes, South Windham has easy gravel biking options. For a more relaxed ride, consider the Air Line Trail – Colchester Spur Trail junction loop from Mono Pond State Park Reserve, which is about 18.5 km long. Another easy option is the Hop State Park Trail – Andover Memorial Bridge loop from Hop River State Park Trail, spanning approximately 24.3 km.

What kind of terrain can I expect on gravel bike trails in South Windham?

Gravel biking in South Windham features a mix of terrain. You'll find hard-packed gravel sections, paved rail trail segments, and dirt woods trails. Some areas, like the unpaved segment of the Mountain Division Trail south of Mallison Falls Road, can be rocky and might be better suited for fat tires. Trails often follow river corridors and weave through lush forests with varied topography.

Are there any long-distance gravel routes in the South Windham area?

For longer rides, the Air Line State Park trail – Air Line Trail loop from Willimantic covers approximately 42.0 km. Another substantial route is the James L. Goodwin State Forest loop from Two Sister's Preserve, which is about 40.9 km and takes you through varied forested areas.

What are some scenic viewpoints or natural attractions along the gravel bike trails?

Many trails in South Windham offer picturesque views, particularly along the Presumpscot and Saco Rivers. The East Windham Conservation Area features loops like the Purple Loop with views of the White Mountains and Little Duck Pond, and the Teal Trail offering excellent mountain views. You can also explore nearby attractions such as Mansfield Hollow State Park and Mansfield Hollow Lake.

Can I find loop routes for gravel biking in South Windham?

Yes, several routes in South Windham are designed as loops. Examples include the James L. Goodwin State Forest loop from Two Sister's Preserve and the East Coast Greenway – James L. Goodwin State Forest loop from Willimantic, both offering circular journeys through diverse landscapes.

What do other gravel bikers say about the trails in South Windham?

The gravel biking routes in South Windham are highly rated by the komoot community, with an average score of 5.0 stars from over 3 reviews. More than 30 gravel bikers have used komoot to explore the varied terrain, often praising the scenic riverine paths and extensive forest preserves.

Are there any trails that follow old rail lines in South Windham?

Yes, the region is known for trails that utilize former rail corridors. The Mountain Division Trail is a significant example, with segments in South Windham following an abandoned rail line. Another route, the Air Line State Park trail – Air Line Trail loop from Willimantic, also follows an abandoned rail line, offering a mix of surfaces.

Where can I find more challenging gravel biking trails in South Windham?

For more challenging rides, the Lowell Preserve offers 'Technical Trails' in its northern part, which are narrower and cover steeper, more difficult terrain. While the listed komoot routes are mostly moderate, the region's diverse forest preserves provide opportunities for more demanding off-road experiences.

What are the main conservation areas that gravel bikers can explore in South Windham?

South Windham boasts extensive conservation areas ideal for gravel biking. The Lowell Preserve features over 8 miles of trails through scenic forests. The East Windham Conservation Area offers an 8-mile network through lush forests and over brooks, forming part of a larger 2,000-acre conservation corridor.

Are there any specific trails that connect different communities or natural features?

The Mountain Division Trail is designed to connect communities and follows the Saco and Presumpscot Rivers, providing scenic views. The Sebago to the Sea Trail is another significant route, connecting Sebago Lake to Casco Bay and passing through Windham with varied terrain.

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Browse the best Gravel rides in other regions.

Airline State Park Trail (Northern Section)WillimanticNatchaug State ForestPutnamQuaddick State ForestBeaver Brook State ParkMoosup Valley State Park Trail

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