The Coastal Challenge is an exciting annual fundraising and squash tournament hosted by Portland Community Squash to support financial aid for families in the community. Established in 2014, the Coastal Challenge brings together players of all ages and skill levels in a day filled with competitive squash, camaraderie, and philanthropy. If you don't play squash, raise the money and have one of the kids play in your spot! This year’s event will take place on Sunday, May 3, with matches starting at 10:00 AM. Our goal this year is to raise $75,000.

The competition features four teams: Portland, Foreside, Cape, and Casco Bay. Each team will comprise:

• 12 adult singles players (48 total)
• 6 doubles players (24 total)
• 6 PCS juniors (24 total)

Each team will compete for three trophies: the Born Cup (winner of the squash tournament), the Coastal Cup (top team fundraising), and the Spaulding Cup (top individual fundraiser).

Event Guide: Link to PDF

Event Video:

Team Captains:

Saco Bay: Mimi Munson, Chris Lutes
Foreside: Max Twine, Alice Ross
Portland: Gus Crothers, Lydia Pillsbury
Cape: Sara Smith, Teddy Stoecklein

2026 HM Payson Coastal Challenge

Fundraising + Athletic Competition for Portland Community Squash

Team Leaderboard

Team Members