The best cycling routes around North Windham
4.7
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9
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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.
Best touring cycling routes around North Windham
- The most popular touring cycling route is Sebago Lake loop — Raymond, Maine, a 39.2 miles (63.2 km) moderate trail that takes 3 hours 44 minutes to complete. This route circles the second-largest lake in Maine, offering varied terrain and scenic views.
- Another top favourite among local touring cyclists is Mountain Division Trail to River Road loop — Westbrook-Windham, an easy 9.6 miles (15.5 km) path. This route incorporates a section of the multi-use Mountain Division Trail, known for its paved surface and rural landscape.
- Local touring cyclists also love the Middle Jam Road & River Road loop via Babb's Bridge — Windham, a 16.1 miles (26.0 km) trail leading through riverine landscapes and past historic landmarks, often completed in about 1 hour 35 minutes.
- Touring cycling around North Windham is defined by picturesque lakes, the Presumpscot River, and extensive woodlands. The network offers options for different ability levels, from easy paved paths to moderately challenging routes.
- The routes in North Windham are highly rated by the komoot community with an average score of 4.5 stars from 7 reviews. More than 70 touring cyclists have used komoot to explore North Windham's varied terrain.
Last updated: April 30, 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 beaches, with the distant foothills of the White Mountains often in sight. The route covers 39.2 miles (63.2 km) and involves a total elevation gain of 1350 feet (411 metres). Expect a varied cycling experience, including both flat sections and some noticeable climbs, which you can complete in about 3 hours and 43 minutes. Keep an eye out for the tranquil waters of Brandy Pond as you make your way around the lake.
Planning your ride around Sebago Lake is straightforward. The route is mostly paved, making it ideal for touring bicycles, though you might encounter unpaved sections if you explore connecting trails. Be aware that major roads like Route 302 and Route 35 South can have significant traffic, but a wide paved shoulder is often available for cyclists. Parking is generally accessible in Raymond, Maine, which serves as a convenient starting point for the loop.
This route provides a unique opportunity to experience the vastness of Sebago Lake, which spans approximately 45 square miles. Beyond the lake itself, you will encounter the scenic Songo River, a natural waterway connecting Sebago Lake to other bodies of water. The blend of lake views, forested areas, and distant mountain backdrops makes this loop a popular choice for exploring the natural beauty of the region.
15.5km
00:57
130m
130m
The Mountain Division and Presumpscot River Loop offers an easy touring bicycle ride, covering 9.6 miles (15.5 km) with 428 feet (130 metres) of elevation gain. You can expect to complete this route in about 57 minutes. As you cycle, you will pass through open woods and farm fields, enjoying exceptional river views. The trail crosses an old railroad bridge over the Presumpscot River, leading you into the Presumpscot River Preserve, where you will find varied terrain from paved sections to hard-packed dirt and some flowy singletrack.
While much of the Mountain Division Trail is flat and straightforward, be aware that the Presumpscot River Trail section can be more rugged. This part of the route may include unpaved, rooty, and steeper segments, which might be more challenging than typical touring cyclists prefer. Always check local conditions before you head out, especially considering the weather, to ensure a pleasant ride.
This route combines smooth rail trail sections with more natural river-side paths, offering a unique blend of environments. Along the way, you can look forward to seeing Babb's Bridge and observing various waterfowl. During spring, you might even spot alewives in the river's rapids, adding a special touch to your touring bicycle adventure.
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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.
4
riders
10.0km
00:36
40m
40m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
6
riders
23.1km
01:32
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
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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Frequently Asked Questions
How many touring cycling routes are available in North Windham?
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.
What is the best time of year for touring cycling in North Windham?
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.
What kind of terrain can I expect on touring cycling routes in North Windham?
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.
Are there family-friendly touring cycling routes in North Windham?
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.
What natural features or landmarks can I see along the touring cycling routes?
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.
Are there any circular touring cycling routes in North Windham?
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.
Where can I park my car when accessing touring cycling routes in North Windham?
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.
What do other touring cyclists say about the routes in North Windham?
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.
Are there any easy touring cycling routes suitable for beginners in North Windham?
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.
Can I bring my dog on touring cycling routes in North Windham?
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.
Are there places to eat or stay near the touring cycling routes in North Windham?
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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