Running trails in Windham, ME
Windham has 6 trails in the directory — 2 on crushed gravel or dirt, 1 loop that returns to the trailhead, 2 with a stated distance, and 1 open 24 hours. 4 of them post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 350 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
Black Brook Preserve
4.4 ★★★★☆ 56 reviews
Nature preserve featuring hiking trails that are open to dogs.
Sebago to the Sea Trail Section 4
4.4 ★★★★☆ 21 reviews
No trails match those filters.
How to pick a trail in Windham
- Match the surface to your legs. Most of what's here is natural surface (2 of 6). Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one. More natural surface trails →
- Loop or out-and-back? 1 trail here is a loop, so you finish back at the car with no backtracking — the easiest way to run a set distance without thinking about it. On an out-and-back you turn round at half your target distance, which makes any trail fit any run. The longest stated distance in Windham is East Windham Conservation Area at 28 mi. 1 trail is long enough for a 5-mile-plus run without repeating yourself.
- Check the hours before a 6am run. 1 trail in Windham is open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 4 of the 6 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 3 have trailhead parking and 1 has restrooms in Windham. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 2 with mile markers, 2 dog-friendly, and 2 smooth and wide enough for a stroller or a wheelchair. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Windham trails by type
Running trails near Windham
Worth the short drive — the closest towns with trails in the directory.