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Routes
Hikes
United States
Maine
Cumberland County

South Windham

The best walks and hikes around South Windham

63

hikers

18

hikes

Hiking around South Windham, Maine, features diverse landscapes encompassing woodlands, wetlands, and significant waterways. The region provides varied environments for exploration, including natural preserves and conservation areas. Key features include the Presumpscot River, forested conservation lands, and numerous ponds, offering a mix of terrain for outdoor activities.

Best hiking trails around South Windham

  • The most popular hiking route is Cherry Hills Trail – Cherry Hills Farm, Gorham, a 2.6 miles (4.2 km) trail that takes 1 hour 4 minutes…

Last updated: May 1, 2026

1

hikers

#1.

Mill Brook Preserve Trail

9.04km

02:25

100m

90m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Zachary
January 24, 2025, Presumpscot River Railroad Bridge

The Presumpscot River is widened either side of the bridge from Gambo Dam, which sits about a half mile downstream. You can see it by hopping off the Mountain Division Trail at the Gambo Road crossing.

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Javi Jaavii
January 31, 2024, Snake Pond

Snake Pond is one of the three ponds that make up the Otter Ponds. This beautiful pond stands as a testament to the glacial activity in the area, formed by receiving water from springs in its kettle hole depression. It's a good place to observe different wildlife, very close to the Mountain Division Trail.

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there are several parking areas to get on the trails. I parked at Shaws Park.

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Frequently Asked Questions

How many hiking trails are available in South Windham?

South Windham offers a variety of hiking experiences, with over 8 routes available for exploration. These trails cater to different preferences, focusing on the region's diverse woodlands, wetlands, and waterways.

Are there easy hiking trails suitable for beginners or casual walkers?

Yes, South Windham is well-suited for easy hikes. All 8 of the routes listed in this guide are rated as easy. For example, you can enjoy the gentle woodlands on the Cherry Hills Trail – Cherry Hills Farm, Gorham, or explore the forested conservation area on the Loop Trail – Lowell Preserve.

Are the hiking trails in South Windham family-friendly?

Many areas in South Windham are excellent for families. Donnabeth Lippman Park, for instance, features a Storybook Trail designed specifically for younger hikers, offering an easy and engaging experience around Chaffin Pond. The trails are generally easy walking on packed earth through wooded areas.

Can I bring my dog on the hiking trails in South Windham?

Yes, South Windham is very dog-friendly. Donnabeth Lippman Park welcomes dogs, particularly on the trail circling Chaffin Pond. Lowell Preserve also allows leashed dogs on its extensive trail network, making it a great option for hiking with your canine companion.

Are there any loop trails in South Windham?

Loop trails are a popular feature in South Windham. You can find several options, such as the Loop Trail – Lowell Preserve, which takes you through a forested conservation area. Another great choice is the Sebago Lake Land Loop – Sebago Lake Land Preserve, offering varied terrain near Sebago Lake.

What natural features or landmarks can I see while hiking in South Windham?

The region boasts diverse natural features. The Presumpscot River Preserve offers exceptional river views, while the East Windham Conservation Area provides scenic viewpoints, potentially including glimpses of the White Mountains and Little Duck Pond. You might also encounter Jewell Falls or explore the Fore River Sanctuary.

Is parking available at the trailheads in South Windham?

Yes, most major preserves and parks in South Windham, such as Donnabeth Lippman Park, Presumpscot River Preserve, Lowell Preserve, and East Windham Conservation Area, typically offer designated parking areas for trail access. It's always a good idea to check specific park websites for detailed parking information before your visit.

What is the best time of year to hike in South Windham?

South Windham offers enjoyable hiking throughout much of the year. Spring brings lush greenery, though some wetland trails can be wet. Summer is popular for its warm weather, while autumn provides stunning fall foliage. Winter hiking is also possible, especially for snowshoeing in parks like Donnabeth Lippman, offering a serene experience.

Are there any trails with boardwalks or bridges over wet areas?

Yes, the Presumpscot River Preserve features boardwalks and bridges, particularly over wet sections, ensuring a more comfortable hiking experience while protecting the natural environment. This allows for easier navigation through varied terrain, including some steeper sections.

Are there any longer hiking options for those seeking more challenge?

While many trails are easy, areas like the Lowell Preserve offer an extensive network of over 8 miles of trails, allowing for longer, combined routes. The East Windham Conservation Area, part of a larger 2,000-acre corridor, also provides numerous trails that can be linked for extended hikes, though the individual routes in this guide are generally shorter.

Are there any accessible trails for individuals with mobility challenges?

The East Windham Conservation Area is actively developing a universal access trail to ensure accessibility for individuals with mobility challenges. This initiative reflects the region's commitment to making its natural beauty available to everyone.

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