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United States
Connecticut
Northeastern Connecticut Planning Region

South Windham

The best cycling routes around South Windham

By Fede from komoot

·

Updated May 31, 2026

If you've ever tried to plan touring cycling around South Windham, you know how quickly the options can become overwhelming. With so many trails and paths, it's tough to figure out which routes are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has ridden, reviewed, and mapped the best touring cycling routes here, and we've distilled all that local knowledge into a curated shortlist. Consider this your shortcut to the rides that truly deliver.

Touring cycling around South Windham is all about gentle exploration. The terrain is generally characterized by mild elevation changes, making it perfect for longer, relaxed rides through diverse landscapes. You'll find a lovely mix of paved rail-trails, picturesque river valleys, and serene forested conservation areas. The region's natural beauty is captivating throughout the year, offering varied backdrops for your outdoor pursuits, from easy paths to more challenging moderate routes.

If you're looking for a relaxed introduction to the area, we'd start with the Colchester Spur Trail junction – Air Line Trail loop from Tyler Field. At 15.4 miles (24.8 km), it's an easy ride that offers extensive views through varied natural settings. For something a bit more substantial, the Andover Memorial Bridge – Andover loop from Willimantic is a fantastic moderate option, covering 29.1 miles (46.9 km) through the local landscape. With more than 60 touring cyclists having explored these routes with komoot, you can trust you're in for a great ride.

If you only do 3 of these routes

  1. 1

    Andover Memorial Bridge – Andover loop from Willimantic
  2. 2

    Hop State Park Trail – Andover Memorial Bridge loop from Willimantic
  3. 3

    East Coast Greenway – James L. Goodwin State Forest loop from Willimantic

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Andover Memorial Bridge – Andover loop from Willimantic

46.9 km

210 m

Moderate

Hop State Park Trail – Andover Memorial Bridge loop from Willimantic

30.5 km

120 m

Moderate

East Coast Greenway – James L. Goodwin State Forest loop from Willimantic

33.3 km

240 m

Moderate

Colchester Spur Trail junction – Air Line Trail loop from Tyler Field

24.8 km

120 m

Easy

James L. Goodwin State Forest loop from Fin, Fur, and Feather Club

48.7 km

450 m

Moderate

1.

Andover Memorial Bridge – Andover loop from Willimantic

46.9km

04:06

210m

210m

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

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4.

Colchester Spur Trail junction – Air Line Trail loop from Tyler Field

24.8km

01:46

120m

120m

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

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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

What types of cycling routes can I expect in South Windham?

South Windham offers a diverse range of touring cycling routes, primarily featuring paved rail-trails, scenic river valleys, and forested conservation areas. You'll find paths suitable for various skill levels, from easy, relatively flat sections to more moderate routes with gentle elevation changes. The region is known for its interconnected trail networks, many of which are multi-use.

Are there any easy touring cycling routes suitable for beginners or families?

Yes, South Windham has options for easier rides. The Colchester Spur Trail junction – Air Line Trail loop from Tyler Field is an easy 24.8 km route that provides a pleasant experience without significant challenges. The Mountain Division Trail, a paved rail-with-trail, is also excellent for families due to its relatively flat terrain and scenic views.

Where can I find parking for cycling routes in South Windham?

For routes utilizing the Mountain Division Trail, convenient parking is available near the South Windham Fire Station. If you're exploring the popular Sebago Lake loop, designated parking and overlook spots can be found, particularly on the southern side of the lake.

Are there any circular touring cycling routes in the area?

Yes, many of the touring cycling routes in South Windham are designed as loops. For example, the Andover Memorial Bridge – Andover loop from Willimantic and the Colchester Spur Trail junction – Air Line Trail loop from Stiles Pond Dam are popular circular options. Additionally, the 39.2-mile loop around Sebago Lake is a highly favored circular route for touring cyclists.

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

Cycling in South Windham offers views of several natural and historical landmarks. The Mountain Division Trail crosses the picturesque Presumpscot River, and a side trail leads to Shaw Park. You can also see the historic Babb's Bridge, a replica of a covered bridge over the Presumpscot River. Nearby attractions include the Air Line & Hop River State Park Trail, Mansfield Hollow State Park, and Mansfield Hollow Lake.

Are there opportunities for wildlife spotting while cycling?

The forested conservation areas and river valleys around South Windham provide excellent opportunities for wildlife spotting. Areas like the Lowell Preserve, East Windham Conservation Area, and Black Brook Preserve offer lush environments where you might encounter local fauna amidst the tranquility of nature.

What do other touring cyclists enjoy most about cycling in South Windham?

The touring cycling routes in South Windham are highly rated by the komoot community, with an average score of 5.0 stars from multiple reviews. Cyclists often praise the varied terrain, which includes paved rail-trails and scenic natural settings, as well as the well-maintained and interconnected trail networks.

Are there any longer touring cycling routes for experienced riders?

For those seeking longer rides, the 39.2-mile loop around Sebago Lake is a prominent attraction offering diverse terrain and stunning views. Among the komoot routes, the Andover Memorial Bridge – Andover loop from Willimantic is a moderate 46.9 km (29.1 miles) trail that provides an extensive touring experience.

Can I access these cycling routes using public transport?

While the region is well-served by its trail networks, specific public transport access points directly to all trailheads might be limited. It's advisable to check local transport schedules and routes if you plan to rely on public transport to reach your starting point.

What is the best time of year to go touring cycling in South Windham?

The diverse landscapes of South Windham, with its paved paths and forested areas, are generally enjoyable from spring through fall. These seasons offer pleasant temperatures and vibrant scenery, making them ideal for touring cycling. While some trails might be accessible in winter, conditions can vary, so checking local weather and trail status is recommended.

Are there any routes that pass through forested areas or offer mountain views?

Absolutely. The region is rich in forested conservation areas. The Hop State Park Trail – Andover Memorial Bridge loop from Willimantic leads through beautiful forested areas and open countryside. The East Windham Conservation Area also boasts an 8-mile trail network featuring scenic mountain and water views, providing an immersive natural experience.

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