Windham

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This map shows trails in Cumberland County

  • Deer Hollow/Mud Pond Nature Reserve — A smallish preserve with unmarked but visible trails and a small platform overlooking the pond. Dogs allowed.
  • Chaffin Pond Preserve at Donna Lippman Park — This is a lovely, kid-friendly place, with a playground, a kids’ trail and a boardwalk. Dogs allowed.
  • Dundee Park — Probably not very fun to walk here during summer, when people flock here to swim at the sandy beach, but this is a pretty and pretty quiet place during the off-season. You’re not allowed to bring dogs here, but I am not sure if that rule applies to the off season? The path is very short.
  • Otterbrook Nature Sanctuary — This was a little neglected when I visited in the fall of 2016. Dogs allowed.
  • Black Brook Preserve — This, in contrast to Otterbrook Sanctuary, was rather lovingly tended to, with many trails, some of them still being developed in the fall of 2016, it seems. I recommend the Diamond Trail. Dogs allowed.
  • Lowell Preserve — More than 300 acres here to explore, although when I visited in the winter of 2017, the trail system seemed to be neglected and it was hard to find my way around. Dogs allowed. Here’s a link to the Cross-Town trails that connects to Lowell Preserve.
  • Sea to Sebago Trail — This long-distance biking or walking path goes from Portland to Sebago Lake theoretically, but it is still in the works. The most developed part, I think, is the section from Windham through Gorham to Standish and the lake — and it’s great. Dogs allowed. Great biking.
  • Windham High School trail — This short (.8-mile or so) trail is unmarked but easily to follow. It starts near the track and heads to the Pleasant River and a little wetland.
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