2025 Summer Trail Challenge

July 1 - August 31 (8pm)

DIscover New Adventures Close to home

Explore the trail network, enjoy views of the White Mountains AND LITTLE DUCK Pond, come across A GLACIAL ERratic, A CAVE, and more. 

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 six 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 six stamps to complete the challenge and be eligible for the prize.  

PARTNERS: REI Co-op of Westbrook Maine, Portland Water District, Windham Parks and Recreation, 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: Otter Ponds | 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 at the link below or with the qr code found on your passport.

PRIZE: Once you’ve completed your passport, bring it to REI (Westbrook location) to receive your exclusive 2025 Trail Challenge Nalgene water bottle—a badge of honor for your summer adventure.

EVENT:  Join us for a kickoff event at REI: “How to Hike for Beginners” Talk Sunday, June 22nd at REI in Westbrook. This talk will go over beginner basics for hiking as well as Trail challenge details.

KEY DATES:

  • Passport Pick-Up Begins: Late June

  • Challenge Runs: July 1 – September 1, 2025

 

2023 Trail Challenge Participants