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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.

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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.

Learn More about Volunteering 

 

2021 ASICS FALMOUTH ROAD RACE ANNOUNCES 8,000 IN-PERSON RUNNERS FOR AUGUST  15 EVENT - Falmouth Road Race

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. 

Support the team!

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. 

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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.

Learn More

 

Thank You


Your kind and generous support provides essential social-emotional learning opportunities to Boston's Youth throughout the summer and school year.

OUR PROGRAMS

Thank You


Your kind and generous support provides essential social-emotional learning opportunities to Boston's Youth throughout the summer and school year.

OUR PROGRAMS

IN PARTNERSHIP WITH