Windham Parks and Recreation
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2025 Summer Trail Challenge

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Get ready for a summer of adventure with the 2025 Trail Challenge, sponsored by the towns of Windham, Westbrook, Gorham, and Standish! This community-wide challenge invites you to explore six of our most popular natural sites—and rewards you for doing it.

HOW IT WORKS: This year’s challenge is centered around a custom-designed trail challenge passport, created in partnership with Perch design firm. Pick up your passport starting in late June. You can pick up your passport at: REI (Westbrook), Windham Town Hall in the Parks & Recreation office, Westbrook City Hall, the Town of Standish, and Gorham Parks & Recreation. Each person participating—kids and adults alike—should have their own passport.  Visit the trails & stamp your journey. Each of the five featured sites will have: a clearly marked sign and a stamp station attached. Use the stamp at each station to mark your passport. You must collect all five stamps to complete the challenge and be eligible for the prize.  

REGISTER: Registration is required by all participants to be eligible to collect the prize. Click the link for more information or to register! - https://www.prlt.org/summer-trail-challenge

The passport is also downloadable here, if you would prefer to print it at home.

1) Landmark: White Mountains Overlook | East Windham Conservation Area, Windham
2) Landmark: Mill Brook Overlook | Mill Brook South Preserve, Westbrook
3) Landmark: Diamond Trail Boardwalk | Black Brook Preserve, Windham
4) Landmark: Snake Pond | Part of the Sebago to Sea Trail, Standish | A free day-use permit is required for access to Portland Water District’s Sebago Lake Land Reserve.  A map of the trails and permit kiosks can be found here: https://www.pwd.org/sebago-lake-land-reserve/
5) Landmark: Gambo Preserve Mill Ring | Gambo Preserve, Gorham

PRIZE: Once you’ve completed your passport, bring it to REI in early September (Westbrook location) to receive your exclusive 2025 Trail Challenge Nalgene water bottle—a badge of honor for your summer adventure. Registrants will be notified when prize pick up officially begins, via email.

PHOTO RAFFLE: Submit your best photos from the challenge to outreach@prlt.org to be entered into a raffle to win a PRLT branded Mirr Coffee Mug.

Challenge Runs: July 1 – September 1, 2025

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