4.7
(3)
29
riders
10
rides
Touring cycling around North Windham offers a diverse network of routes through scenic landscapes. The region is characterized by numerous lakes, including Sebago Lake, and rivers like the Presumpscot, with trails often running alongside them. Extensive forests and woodlands provide shaded paths, while some areas offer distant views of the White Mountains. The trail network includes both paved and unpaved sections, catering to various cycling preferences.
Last updated: August 8, 2026
4.0
(1)
3
riders
63.2km
03:44
410m
410m
Embark on the Sebago Lake loop, a moderate touring bicycle route that offers expansive views of Maine's second-largest lake. You will cycle through diverse landscapes, passing by woodlands and sandy…
15.5km
00:57
130m
130m
The Mountain Division and Presumpscot River Loop offers a delightful blend of smooth rail trail and natural riverside paths, making it a unique touring cycling experience. You'll pedal through open…

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25.9km
01:35
190m
190m
Cycle the 16.1-mile Middle Jam Road & River Road loop via Babb's Bridge in Windham, Maine, a moderate route with scenic river views.
5.0
(1)
7
riders
23.1km
01:32
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
8
riders
12.5km
01:15
190m
190m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The Presumpscot River is widened either side of the bridge from Gambo Dam, which sits about a half mile downstream. You can see it by hopping off the Mountain Division Trail at the Gambo Road crossing.
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I love this bridge. But, a dump truck tried to cross it and collapsed the floor. Not sure the repair time frame. 9/21/24
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Snake Pond is one of the three ponds that make up the Otter Ponds. This beautiful pond stands as a testament to the glacial activity in the area, formed by receiving water from springs in its kettle hole depression. It's a good place to observe different wildlife, very close to the Mountain Division Trail.
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The Mountain Division Trail is a mixed-use trail. It is a mix of paved and unpaved trail. The paved part of the trail is built along an old railbed. There are plans to extend the trail all the way to Portland.
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Brandy Pond is big enough that it also goes by the name Bay of Naples Lake. It is one of a few lakes in this area and is connected to Long Lake by the Chute River and to Sebago Lake by the Songo River.
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Sebago Lake is the second-largest reservoir within the state of Maine, encompassing roughly 45 square miles. This is an official overlook spot and parking area on the southern end of the lake. The more popular state park is on the northern side of the reservoir.
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Sebago Lake is the second-largest reservoir within the state of Maine, encompassing roughly 45 square miles. This is an official overlook spot and parking area on the southern end of the lake. The more popular state park is on the northern side of the reservoir.
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Brandy Pond is big enough that it also goes by the name Bay of Naples Lake. It is one of a few lakes in this area and is connected to Long Lake by the Chute River and to Sebago Lake by the Songo River.
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North Windham offers a selection of 9 touring cycling routes, catering to various preferences. These include 6 easy routes and 3 moderate routes, ensuring options for different skill levels.
The best time for touring cycling in North Windham is typically from spring through fall. During these seasons, the weather is generally pleasant, allowing cyclists to fully enjoy the diverse landscapes, from lakeside paths to forested trails and river views. Winter cycling might be possible on some cleared paths, but many trails could be snow-covered.
You can expect a mix of terrain. Many routes feature mostly paved surfaces, such as sections of the Mountain Division Trail, making them accessible for touring cyclists. Other areas might include unpaved sections, gravel paths, or even some moderately challenging mountain biking segments, especially in the northwestern part of the Sebago to the Sea Trail system. Routes often follow rivers, skirt lakes, and wind through extensive woodlands.
Yes, North Windham has several family-friendly options. The Mountain Division Trail to River Road loop — Westbrook-Windham is an easy 9.6-mile path that incorporates a paved section of the multi-use Mountain Division Trail, which is ideal for all ages and skill levels. Another easy option is the Mountain Division Trail – Snake Pond loop from Little Falls, which is 10.8 miles long.
Cycling in North Windham offers access to a rich tapestry of natural beauty and points of interest. You can enjoy views of picturesque lakes like Sebago Lake and Snake Pond, ride alongside the Presumpscot River, and explore extensive forested areas. Historic landmarks include Babb's Bridge, a replica of a 19th-century covered bridge, and the ruins of a canal and the Oriental Powder Mill along the Mountain Division Trail. Some trails, particularly in the East Windham Conservation Area, even offer distant views of the White Mountains.
Yes, many of the touring cycling routes in North Windham are designed as loops. For example, the popular Sebago Lake loop — Raymond, Maine is a 39.2-mile moderate trail that circles the second-largest lake in Maine. Another option is the Middle Jam Road & River Road loop via Babb's Bridge — Windham, a 16.1-mile route through riverine landscapes.
Access points for major trails like the Mountain Division Trail often have designated parking. For instance, you can find parking near the South Windham Fire Station or off Gambo Road. For routes around Sebago Lake, there are official overlook spots and parking areas on the southern end of the lake. It's always advisable to check specific route details for the most convenient parking locations.
The touring cycling routes in North Windham are highly rated by the komoot community, with an average score of 4.5 stars from 7 reviews. Cyclists often praise the diverse landscapes, from scenic lake views to peaceful forested paths, and the variety of terrain that caters to different abilities.
Absolutely. North Windham offers 6 easy touring cycling routes perfect for beginners or those looking for a relaxed ride. The Mountain Division Trail to River Road loop — Westbrook-Windham is a great example, featuring a paved surface and rural scenery. Another easy option is the Half Moon Trail – Snake Pond loop from Sebago Lake, which is 9.3 miles long.
While many outdoor areas in Maine are dog-friendly, specific rules can vary by trail and land manager. It's generally recommended to keep dogs on a leash and ensure you clean up after them. For specific routes, it's best to check local regulations or signage at the trailhead to confirm if dogs are permitted and under what conditions.
North Windham and the surrounding areas offer various amenities for cyclists. You'll find cafes, pubs, and accommodation options within reasonable distance of many popular trails. For instance, areas around Sebago Lake and along the Mountain Division Trail often have services available, allowing you to refuel and relax after your ride.


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