Best trails in Windham, Maine

558 Reviews
Looking for a great trail near Windham, Maine? AllTrails has 8 great hiking trails, forest trails, wildlife 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 Wolfes Neck Woods State Park or Mackworth Island State Park, we've got you covered. You'll also find some great local park options, like Pleasant Mountain Preserve or Town of Harpswell. Just looking to take a quick stroll? We've got 7 easy trails in Windham ranging from 0.8 to 2.5 miles and from 187 to 318 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Windham, Maine
Top trails (8)
#1 - Lowell Preserve
Windham, Maine
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(306)
Length: 4.3 mi • Est. 2 h
Note: As of 9/8/20, users have reported that the right hand side of the yellow trail is closed. The Lowell Preserve is over 300 acres of a forested conservation area that has over 8 miles of trails for all types of users from hikers to ATV users. This wooded trail system consists of a number of loops ranging in length from 0.3 to 3.4 miles. The trails are a mixture of packed earth and rocky surfaces that have various elevation inclines throughout the area, and are used by hikers, mountain bikers, snowshoers, cross-country skiers, horseback riders, and snowmobilers. The Lowell Preserve consists of three main trail loops marked by yellow, blue and green blazes. The yellow-blazed loop is called the Libby Hill Loop Trail and circumvents the boundary of the property, almost 3.5 miles. Most of the Libby Hill Loop Trail is for hiking, mountain bikes and ATV users. The blue-blazed trail is called the Virginia Trail and heads towards the center of the property, looping back after ending about half way into the property. The Virginia Trail is 1.7 miles in length. The green-blazed trail is called the Roscoe Loop trail and is a 1.5 mile loop in the northern section of the property. Orange and red blazed connector trails link the main loops. Follow the link below for a map showing the trail names and blaze colors. Allowed uses within the trail network include hiking, mountain biking, horseback riding, ATVing, cross-country skiing, snowshoeing, and snowmobiling. Trails and trail sections are marked to show allowed uses. Please respect the signs.Show more
#2 - Chaffin Pond
Donnabeth Lippman Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(85)
Length: 1.1 mi • Est. 27 m
The Donnabeth Lippman Park formerly known as the Chaffin Pond Preserve is a 123 acre wooded area in northern part of Windham. There is a 10 acre pond on the property that is a great fishing hole for all ages. The Donnabeth Lippman Park offers easy walking on packed earth through wooded areas and around the edge of Chaffin Pond. The park's main trail loops around Chaffin Pond, but there are also trails on the east side of the pond that leave and connect back to the main loop. A trail extension on the north side of Chaffin Pond leads to Mud Ponds. These trails on the back side of the pond can be very wet during the spring season; however, these trails are an easy family hike that is in a great natural setting. Picnic tables and benches near the trailhead make this a great place for a picnic.Show more
#3 - Gilman Falls
Windham, Maine
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(81)
Length: 2.5 mi • Est. 1 h 8 m
#4 - Black Brook Preserve Loop
Black Brook Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(59)
Length: 1.8 mi • Est. 47 m
The Black Brook Preserve trail network has rolling hills, mature trees, and brooks along with a variety of wildlife and plant life. The trails are great location for bird watching and enjoying the historic charm of Windham. There are several miles of trails that cross through all areas of the Black Brook Preserve with over 600 feet of bog bridges to protect the wetlands and keep hikers feet dry. Cedar benches scattered along the trail to sit and enjoy the silence or have a snack. The historic charm, rural character and natural beauty that Windham is known for can all be found in the rolling hills, mature trees, and brooks of the preserve. There is also a wide variety of wildlife, plant life, and birds. Deer, beaver, coyote, fox, porcupines, raccoons, wild turkeys, partridge, skunks, owls, & egrets are among the wildlife seen here. This natural forested wetland is a haven for herons, ducks, songbirds, and fish. The preserve's newest residents are beavers; their dams and lodges can easily be found in the center of the preserve and along the trails that touch the brook. The Black Brook forms here in the Preserve and begins its journey meandering along through fields and forests until it empties into the Presumpscot River, which serves as part of Windham's western border six miles away.Show more
#5 - Deer Hollow Sanctuary Trail
Windham, Maine
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray Star(10)
Length: 0.8 mi • Est. 19 m
This unmarked but easily followed trail leads down to Mud Ponds and loops around the smaller of the two ponds through nicely wooded areas. The backside of the trail between the two ponds provides an unexpected sense of wilderness and remoteness. The wetland and pond habitats provide great bird watching. A short trail leads down to an observation tower on the edge of the pond which provides a great vantage point to view wildlife and survey Mud Ponds. This tower may be difficult to access at times of year when the water in the ponds is high, as the ground can be very wet. , located on a 16-acre sanctuary, leads down to Mud Ponds. Great for a short hike and bird watching. Can be wet in the spring. Trails are not marked but easily followed.Show more
#6 - Windham High School Trail
Windham, Maine
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(4)
Length: 0.9 mi • Est. 27 m
This network offers short wooded trails that initially follow gravel roads before descending a moderately steep hill to loop around the Pleasant River and small wetland area. The trails can be combined with walks around the athletic fields and school campus to add more distance.This looping trail was designed for the school's cross-country running team. Show more
#7 - North Gorham Dam to Dundee Dam Paddle
Presumpscot River Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(3)
Length: 1.5 mi
#8 - Otter Brook Preserve Trail
Otter Brook Preserve Trail
easyYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarGray StarGray Star(5)
Length: 1.6 mi • Est. 40 m
The trailheads are not marked but leave directly from the pullouts and are easy to find. Once on the trail, blue laminated signs mark the trail as it follows Otter Brook. On the northern end, the trail follows snowmobile trails briefly so users should pay attention to signs to be sure to stay on the correct trail. This trail, especially the southern end, can be very wet in the spring and generally follows the uneven forest floor. Make sure to be prepared for these conditions.Show more