Family-Friendly Trails in Windham, Maine

Windham offers families plenty of ways to spend time outdoors, from pond loops and woodland walks to paved bike rides and trails with mountain views. Whether you’re introducing little ones to hiking, bringing a stroller, or planning a longer adventure with older kids, there’s a trail to match your family’s pace.

These local trail systems make it easy to fit nature into your day. Enjoy a short walk before playground time, pause along a boardwalk to look for wildlife, or pack snacks and spend a morning exploring farther into the woods.

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Lowell Preserve

Located behind the East Windham Fire Station, Lowell Preserve offers woodland trails with room to explore as your family grows. Start with one of the main loops, combine routes for a longer outing, or finish your visit with time at the nearby playground.

Blue Loop

Distance: Approximately 1.5 miles
Difficulty: Easy

A wide woodland loop with gradual hills, forest scenery, and interesting rocks and trees to notice along the way.

Highlights:

Wide forest paths
Manageable family hiking distance
Nearby playground

Red Loop

Distance: Approximately 1.5 miles
Difficulty: Easy

Another approachable option for families ready to explore beyond their usual route. The main loop offers a shorter adventure within the preserve’s larger trail network.

Highlights:

Wooded loop hike
Gentle changes in elevation
Opportunities to extend your outing

Blue & Red Loops Combined

Distance: Approximately 3 miles
Difficulty: Easy to Moderate

Combine the two main loops for a longer forest outing. This is a good next step for children who are comfortable with shorter hikes and ready to build endurance.

Highlights:

Longer family hike
Connected woodland loops
Options for further exploration

👉 Read the full Lowell Preserve guide

Donnabeth Lippman Park

Chaffin Pond at Donnabeth Lippman Park combines a nature walk with plenty of reasons to pause along the way. Pond views, boardwalks, a StoryWalk, and a nearby playground make this an especially appealing stop for families with younger children.

Chaffin Pond Loop

Distance: Approximately 1.2–1.5 miles, depending on the route and side paths
Difficulty: Easy

Follow the trails around Chaffin Pond through woods and wetland edges. Leave extra time to look for turtles, watch birds, and explore the StoryWalk before finishing at the playground.

The natural surface includes packed dirt, pine needles, and boardwalks. An all-terrain stroller is the better choice if you bring one, and some sections may be wet or uneven.

Highlights:

Scenic pond views
Boardwalk sections
StoryWalk
Wildlife-watching opportunities
Playground and picnic area nearby

👉 Read the full Chaffin Pond guide

East Windham Conservation Area

East Windham Conservation Area offers opportunities for both gentle walks and longer woodland adventures. Its universal access trail gives families another option for exploring with a stroller or mobility device, while connecting trails allow experienced hikers to venture farther.

Universal Access Trail to the Overlook

Distance: Approximately 3 miles round trip to the overlook, based on my tracked walk
Difficulty: Easy terrain; a longer outing for little legs

This compacted stone-dust trail gradually climbs toward a scenic overlook with views of mountains in western Maine and New Hampshire. It’s a wonderful option when you want forest scenery and a destination to work toward without navigating a traditional rocky hiking trail.

On my visit, I tracked approximately 1.5 miles to reach the overlook. Plan for the return trip, too, or enjoy a shorter out-and-back walk if that better suits your family.

Highlights:

Smooth stone-dust surface
Gradual slopes
Stroller- and wheelchair-friendly trail
Scenic mountain overlook
Option to turn around for a shorter walk

👉 Read the full Universal Access Trail guide

Connecting Woodland Trails

Distance: Varies by route
Difficulty: Easy to Moderate, depending on the trails selected

Families looking for more exploring can use the wider trail network, including connections toward Little Duck Pond and Lowell Preserve. Check the trail map before starting, as surfaces and difficulty vary beyond the universal access trail.

Highlights:

Longer hiking options
Pond and woodland scenery
Connections to neighboring conservation land
Routes for experienced young hikers

Explore the East Windham Conservation Area trail information and map.

Black Brook Preserve

Black Brook Preserve offers a mix of forest, wetlands, and brook scenery. Its connected trails make it a good place for children who enjoy noticing the smaller details of a walk, from water moving beneath a bridge to birds calling overhead.

Black Brook Preserve Loop

Distance: Approximately 1.7–1.8 miles, depending on the route
Difficulty: Easy to Moderate

A woodland outing through rolling terrain with bog bridges crossing wetter sections. Families can pause at benches along the way for a snack or a quiet moment in the woods.

Highlights:

Woodland and wetland scenery
Bog bridges
Brook views
Benches for rest stops
Connected trail options

Find trail details and a map from the Presumpscot Regional Land Trust.

Gilman Falls

Gilman Falls offers a riverside destination for families who enjoy a little more adventure. The route leads toward a dam and rapids along the Presumpscot River, with the moving water providing a memorable turnaround point.

Gilman Falls Trail

Distance: Approximately 2.5 miles out and back
Difficulty: Easy to Moderate; some route-finding needed

Much of this walk follows an ATV and snowmobile track, including a stretch beneath power lines. The route is not consistently marked, making it better suited to families comfortable following a map and navigating trail junctions.

Keep children close around the river and enjoy the falls from a safe distance.

Highlights:

Presumpscot River scenery
Dam and rapids
Out-and-back adventure
Best suited to confident young hikers

View a detailed Gilman Falls route description.

Mountain Division Trail

The Mountain Division Trail is a useful option for families who want to walk, push a stroller, or bring bikes and scooters. Following a historic railroad corridor, its paved sections offer a different experience from Windham’s natural-surface hiking trails.

Paved Trail from Gambo Road

Distance: Choose your own out-and-back distance
Difficulty: Easy

Start near the Gambo soccer fields and enjoy the paved recreation path, turning around whenever your family is ready. A short stroll works well for toddlers, while riders can cover more ground on bikes or scooters.

For a simple first visit, travel half a mile before turning around for a one-mile outing. Stay on the paved section if you’re looking for the easiest surface for small wheels.

Highlights:

Paved walking and riding surface
Stroller-friendly option
Great for bikes and scooters
Flexible distance
Historic railroad corridor

👉 Read the full Mountain Division Trail guide

Quick Picks for Families

Best for toddlers: Chaffin Pond at Donnabeth Lippman Park
Pond views, a StoryWalk, and playground time offer plenty of motivation for little explorers. Walk only part of the trail if the full loop feels too long.

Best for strollers, bikes, and scooters: Mountain Division Trail
The paved surface and flexible turnaround point make it easy to plan around your family’s energy.

Best for mountain views: Universal Access Trail at East Windham Conservation Area
A gradual stone-dust walk leads to a scenic overlook. Allow for approximately three miles round trip based on my tracked visit.

Best trail and playground combination: Lowell Preserve
Choose a main woodland loop, then finish with time at the nearby playground.

Best for wetland exploring: Black Brook Preserve
Bog bridges, brooks, and forest scenery give curious kids plenty to notice.

Best for a longer woodland hike: Lowell Preserve’s Blue & Red Loops
Combine the loops for approximately three miles of exploring.

Windham makes it easy to enjoy outdoor time close to home, whether you have an hour after school or a whole morning to explore. Start with a distance that feels comfortable, bring a snack, and leave room for the stops that make hiking with kids worthwhile.

Return throughout the seasons to watch familiar places change. A favorite pond loop or woodland trail can feel like a new adventure when there are frogs to listen for, colorful leaves to collect, or fresh tracks in the snow.

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