Support us through Events
4K Trail Run
Thursday, June 26th, 2025
Experience the beauty of Cathleen Stone Island while supporting a great cause! Join your sponsoring company's team or register as an individual for an evening of running, fundraising and celebration. Following the 4K Trail Run, enjoy a delicious buffet, unlimited beer and non-alcoholic beverages, and a sunset cruise back to downtown Boston.
Not a runner? Want to come for free? Sign up to volunteer during the event and enjoy the post-race festivities! Volunteers help direct runners, distribute t-shirts and water, and assist finish line technicians.
Falmouth Road Race & 2026 Boston Marathon
Falmouth- August 17th, 2025
Team CSIOBS is a proud partner of the ASICs Falmouth Road Race for the 4th year in a row. We are excited to run this historic and prestigious road race, alongside some of the world's best runners, all while supporting Boston students and enjoying an amazing day on Cape Cod! Applications are closed for 2025.
Boston Marathon- April 20th, 2026
After a great 2025 campaign which saw 6 champions raise over $60,000, we are excited to partner again with the Boston Marathon in 2026.
Applications not yet open. If you are interested in joining the waitlist, email Jackson Donahue with your name and a brief bio including your connection to our organization and fundraising background.
Learn More About Falmouth and the Boston Marathon
Evening Expedition Gala
November 5th, 2025
As our largest annual fundraiser of the year, the Evening Expedition Gala brings together 500 community-minded corporate employees and local philanthropists to celebrate the thousands of young people participating in Cathleen Stone Island Outward Bound education programs each year. Join us to celebrate a year of learning, reflection and transformation for Boston students.
ISLE BBQ
2026- TBA
Join us on the island for a beautiful evening including a full BBQ dinner, open beer & wine bar, lawn games, beach bonfire, networking, fantastic city & sunset views ... and more!
Thanks to all who joined us in June of 2025!
Fishing Invitational
2026- TBA
Join us for an exclusive Fishing Invitational, where a small group of anglers vie for the largest fish and most catches! This experience includes a full day of fishing in Boston Harbor with a professional guide, breakfast and lunch onboard, and a post-reception dinner on Cathleen Stone Island with awards! This event is by invitation only. Please contact Shakira Floyd at [email protected] if interested!
Thank you to all our guides and anglers who made this a great event in 2025.
Thank You
Your kind and generous support provides essential social-emotional learning opportunities to Boston's Youth throughout the summer and school year.
