Looking for a great trail near Windham, Maine? AllTrails has 6 great hiking trails, snowshoeing trails, dogs leash trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Bradbury Mountain State Park or Wolfes Neck Woods State Park, we've got you covered. Just looking to take a quick stroll? We've got 4 easy trails in Windham ranging from 0.8 to 1.6 miles and from 219 to 318 feet above sea level. Start checking them out and you'll be out on the trail in no time!

hiking

snowshoeing

dogs on leash

Windham, Maine Map
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hiking
bugs
rocky
13 days ago

Has a new kid's storywalk. Partially an ATV trail. Brook has new bridge. Well marked. Wear ORANGE - hunting is allowed.

hiking
bugs
over grown
30 days ago

hiking
1 month ago

Lots of exposed tree roots, but fun trail. We heard, but did not see a pilliated woodpecker.

hiking
2 months ago

What a perfect weather day for a short leasurely hike. A bit Buggy. My bad as I didn’t use repellent. Yes I would do it again. Well groomed and easy access. Thanks to Windham Park and Rec!

hiking
bugs
3 months ago

hiking
muddy
4 months ago

hiking
muddy
5 months ago

hiking
bridge out
muddy
snow
washed out
5 months ago

Nice trail close to home. Went with the dog today. It’s mud season now so the trail reflects that . Some Parts are completely washed out, some super muddy , walked by a collapsed bridge. The big stream was tricky to cross without it. The trail we took was pretty well marked. Will return to the preserve to try another trail.

hiking
5 months ago

dust..dirt ..mud..bring it...

This trail is not maintained very well. This is more of an outdoor survival training kind of trail, rather than a fun recreational trail. There are many dangerous looking widow makers, and the foot bridges have rotting timbers and exposed nails. Going in through the southern trail head took me through a prickly raspberry patch. The northern trail head was better maintained for snowmobiles. Once off the snowmobile track the path was difficult to follow. Did I mention all the poison ivy?

Lots of improvements to this preserve since I last visited it. Hawkes Trail has been modified to include a change in the midsection. A section has been close (marked) and a new route created. Improvements include new catwalks and information stations. A few new trails too. Watch out for the poison ivy which is prevalent throughout.

Sunday, September 16, 2018

hiking
Saturday, June 09, 2018

Nice short walk. Great for families. Has a storybook trail where kids can read a book while they walk. Also has a playground and picnic tables. Bring bug spray

hiking
Saturday, June 02, 2018

Most of this trail is wonderfully marked, and then on Diamond Trail... you end up in a meadow FULL of ticks. It was nightmarish... our family of four were covered in appx 20 ticks a piece, and there were still ticks in our car the next day. (One fell from the ceiling onto my 5 yo's head. Good times.) So, when you get to the meadow, I highly recommend that you turn around!

hiking
Saturday, May 05, 2018

Trying to find a positive..... Well, we crossed one nice little brook. That’s about it. Lots of flooded sections (even taking into consideration the time of year), poor signage, lots of logging activity, and dirt bike riders blowing past us. Too many good alternatives nearby to try this one again.

Tuesday, April 24, 2018

One of my favorites for both my dog and child! Great intro into hiking with the kids, and having the playground to go on afterwards. The dog could hop in the pond and was very happy. It may only be just more than a mile, but if you want to make it longer you can loop the other colored trails. Will try going to the connected trails next time!

hiking
Monday, April 23, 2018

Solid local hike. Couple of nice boggy areas with some birds. Fairly tucked underneath the trees most the hike. Would be a great trail run with the amount of different trails you can attack.

hiking
Monday, February 12, 2018

Good trail, will keep it in mind for summer runs. Hard to follow at points - very clearly marked sometimes, but be careful not to venture too far north particularly on snowmobile trails and get off track

walking
Saturday, November 04, 2017

Quite a bit of tree damage from the recent storm. A few large trees fell across the Green trail and one on the Orange trail.

Tuesday, October 24, 2017

Great short hike. Several loops to add together.

Thursday, October 05, 2017

Great place for trail running. But be aware of where you are it connects to the North Falmouth Community Forest and easily adds on several miles.

hiking
Saturday, September 23, 2017

We did the Libby Loop trail which is the perimeter trail of the preserve. There are some pretty places along this trail and some not so pretty that go through cutover areas. We hiked it when it had been dry for a while, but you could tell that if it had been rainy that several areas would be muddy, so if hiking during wet weather, you will want boots. Signage is difficult, what with so many trails. There are large yellow arrow signs meant for ATV's, so if you are following the yellow Libby Loop signs, ignore the large arrow signs. Parts of the Libby Loop have only green signs where they combine with another trail, and the parts around the top of the Loop down toward Little Duck Pond don't have any signs. I had the map on my phone and used this to make sure I did not go the wrong way. Overall, I liked this hike, it had some hills and was a nice walk through the woods close to my home. This is not a destination hike where you will be wowed by the magnificent views, but is a nice getaway. Warning ! The preserve allows hunting, so be sure to wear hunter orange on yourself and on your dogs during hunting season. And no WHITE!

on Chaffin Pond

walking
Monday, September 04, 2017

Nice and easy stroll through the woods. I love to bring my daughter here because of the playground and also the designated "story trail" for the kids. It is a nice, well kept area.

snowshoeing
Friday, August 04, 2017

5 minutes from home, perfect for getting in a couple hours of hiking or snowshoeing after work. The trails are well marked and easy to follow even at night with a headlamp. A few short new connector trails have been added in the past year, allowing you to meander without having to follow the same loops all the time. If you're following the Diamond Trail and reach the open grassy area, you can follow Diamond till you hit the grey (snowmobile) trail and get back to the parking area, but in spring-fall it's marshy and in the winter it's packed hard by sleds. Instead, turn left and follow the green (Deer) trail along the treeline, you'll come to a trail map at an opening in the trees with a new bridge just inside the treeline that meets the Hawkes Trail (red.) Follow this to the right to head back toward the southern end of the Diamond Trail (via the Pine Grove Trail) and the parking area. Or for a bit of hills, take the Momentum Trail - it's fun on snowshoes after a fresh dumping!(See the current trail map I posted.) The bugs are ferocious, especially the deer flies, so make sure to bring insect repellent. The open grassy area is FULL of ticks so long pants treated with permethrin are a good idea.

Wednesday, May 31, 2017

nice easy hike close to home

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