3.7
(3)
81
riders
18
rides
Road cycling around North Windham offers diverse terrain characterized by picturesque lakes, winding rivers, and extensive woodlands. The region features prominent waterways like Sebago Lake and the Presumpscot River, providing scenic backdrops for routes. Cyclists encounter varied landscapes, from paved multi-use trails to roads traversing rural areas and forested sections. This blend of natural features creates a compelling environment for road cycling.
Last updated: May 13, 2026
3.0
(1)
22
riders
64.8km
02:54
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
17.6km
00:54
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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27.3km
01:20
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
16
riders
47.8km
02:17
360m
360m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
41.2km
01:50
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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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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At the end of Old Town Landing Road is a small public boat launch. You can pretty much bike to the water's edge, and if you want to stick around for a minute, there are some rocks where you can park your bike and soak in the view.
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Gilman Road takes you past Fels-Grove Farm Preserve. The natural woodlands make this a shaded stretch of road, much appreciated in the warmer summer months.
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First Falls is a set of rapids and small cascades on the Royal River. You get a great view from here on the Main Street Bridge, or you can hop off the bike at Grist Mill Park and get right next to the edge of the water.
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A great view of the bridge crossing over the Presumpscot River, just below Presumpscot Falls. A great place to start your journey.
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Gilman Road takes you past Fels-Grove Farm Preserve. The natural woodlands make this a shaded stretch of road, much appreciated in the warmer summer months.
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Royal River Park is a small, scenic park next to the Royal River and just southeast of the Yarmouth History Center. This is a nice place to pause on a long ride and take a break from being in the saddle.
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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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North Windham offers a diverse selection of over 15 road cycling routes, catering to various skill levels and preferences. These routes explore the region's picturesque lakes, winding rivers, and extensive woodlands.
The best time for road cycling in North Windham is typically from spring through fall, when the weather is mild and the natural scenery is at its peak. The region's lakes, rivers, and woodlands provide a beautiful backdrop during these seasons. While winter cycling might be possible on some cleared paths, many routes are best enjoyed in warmer months.
North Windham's road cycling terrain is quite varied. You'll find everything from easy, paved multi-use trails like the Mountain Division Rail Trail to moderate routes with rolling hills and varied surfaces. The landscape often features scenic lake views, riverine paths, and sections through lush woodlands, with some areas offering distant views of the White Mountains.
Yes, North Windham has several easy road cycling routes perfect for beginners. For instance, the Mountain Division Rail Trail is an easy, paved path known for its rural landscape, ideal for a relaxed ride. There are 9 easy routes out of the 17 available in the area.
For experienced cyclists seeking a challenge, North Windham offers routes with more significant elevation changes and longer distances. While most routes are easy to moderate, there is at least one difficult route available, providing a more strenuous experience through the region's varied terrain.
Many road cycling routes in North Windham pass by interesting landmarks and natural features. You might encounter historic structures like Babb's Bridge or the Presumpscot River Railroad Bridge. The River Road & Middle Jam Road loop via Babb's Bridge — Windham is a great example of a route that combines riverine landscapes with historic sights.
Absolutely. The region is known for its scenic beauty, and many routes offer picturesque views. The Sebago Lake loop, for example, provides stunning lake views as it circles Maine's second-largest lake. You can also find viewpoints like the View of Sebago Lake and serene spots like Snake Pond.
The road cycling experience in North Windham is highly rated by the komoot community, with an average score of 3.7 stars. Reviewers often praise the diverse terrain, the scenic beauty of the lakes and rivers, and the variety of routes that cater to different ability levels, from easy paved paths to more challenging loops.
Yes, parking is generally available at various access points for road cycling routes in North Windham. Many trailheads and parks, such as Donnabeth Lippman Park and Lowell Preserve, offer designated parking areas for outdoor enthusiasts.
North Windham offers several family-friendly road cycling options, particularly on its paved multi-use trails. The Mountain Division Rail Trail is an excellent choice for families due to its easy grade and paved surface. Dundee Park, with its beach and picnic area, also provides a great destination for a family outing.
Yes, many of North Windham's road cycling routes are designed as loops, offering a continuous and varied ride. Popular examples include the Sebago Lake loop, which circles the expansive lake, and the River Road & Middle Jam Road loop via Babb's Bridge — Windham, which explores riverine landscapes.
The road cycling routes in North Windham vary significantly in length. You can find shorter, easy rides like the Mountain Division Rail Trail, which is about 17.6 km (10.9 miles), up to longer, more extensive tours such as the Sebago Lake loop, covering approximately 64.8 km (40.3 miles).


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