2025 Summer Trail Challenge

July 1 - August 31 (8pm)

DIscover New Adventures Close to home

  1. Register for the Challenge using the form below.

  2. Learn about the Challenge using the instructions below.

  3. Share the Challenge with a friend.

InStructions for The Challenge:

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, Westbrook City Hall, Standish Town Hall, 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.  

PARTNERS: REI Co-op of Westbrook Maine, Westbrook Community Center, the City of Westbrook, Portland Water District, Windham Parks and Recreation, the Town of Windham, and Gorham Parks and Recreation

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 & Shaw Park | Gambo Preserve, Gorham

REGISTER: Registration is required by all participants; you may do so with the above form.

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.

KEY DATES:

  • Passport Pick-Up Begins: Late June

  • Challenge Runs: July 1 – September 1, 2025

Trail Challenge Landmark Locations:

 

2023 Trail Challenge Participants