Looking for fun and accessible outdoor adventures for the whole family? Windham, Maine, is home to a variety of trails perfect for a weekend hike, nature walk, or casual stroll with the kids. Whether you want to explore forested paths, visit a pond, or walk along a historic railway, there’s something for everyone. Let’s dive into the best trails Windham has to offer!

1. Lowell Preserve
Located behind the East Windham Fire Station, Lowell Preserve offers a mix of trails for different skill levels:

• Blue and Yellow Trails: 1.8 miles with a 203 ft elevation gain, taking around 37 minutes to complete — perfect for a quick family hike.
• Red and Orange Loop: A more challenging 3.9-mile hike with a 413 ft elevation gain, taking about 1 hour and 32 minutes — great for older kids who love an adventure. With clearly marked trails and peaceful wooded surroundings, Lowell Preserve is a wonderful spot for a family outing.

2. Chaffin Pond at Donnabeth Lippman Park
For a more relaxed walk, visit Donnabeth Lippman Park and explore the Chaffin Pond Yellow Trail — a 1.1-mile loop that circles the pond. The mostly flat path takes about 20 minutes to complete, making it ideal for little legs. Families will also love the Story Walk along the trail, where children can read pages of a storybook as they walk, combining literacy with nature.

3. East Windham Conservation Area
One of Windham’s newest trail systems, acquired in 2023, the East Windham Conservation Area features a 3.5-mile loop with a 459 ft elevation gain, taking roughly 1 hour and 28 minutes to hike. Adventurous families can also connect to Lowell Preserve for an extended trek. This trail offers beautiful views and is perfect for those looking to explore less crowded paths.

4. Black Brook Preserve
If you’re looking for a short and sweet outing, check out the Black Brook Preserve trail. This 1.8-mile loop takes about 36 minutes to complete and offers a peaceful escape into nature. It’s a great choice for families wanting a brief hike with scenic views.

5. Gilman Falls
For a bit of a “wow” factor, the Gilman Falls trail is a 2.5-mile out-and-back hike that leads to a stunning waterfall along the Presumpscot River. With a 167 ft elevation gain, this trail takes about 53 minutes to finish. It’s an exciting option for families eager to reward their hike with a beautiful natural feature.

6. Mountain Division Trail
This family-friendly, multi-use trail starts at the Gambo soccer fields. You can walk:

• 4 miles along the paved portion of the historic Sebago to the Sea Trail heading toward Standish.
• Or, go 6 miles in the opposite direction toward Westbrook. The first mile is paved, followed by 1.5 miles of gravel, with the remaining path running along railroad tracks. The paved sections are especially popular with families — perfect for strollers, scooters, and bikes.

Plan Your Next Adventure
Whether you’re looking for a short stroll, a waterfall adventure, or a paved path for biking with kids, Windham’s trails offer something for every family. Pack some snacks, grab your water bottles, and head outside to explore these beautiful spots together. Happy hiking!