Support us through Events
4K Trail Run
May 20th and 21st, 2026
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.
More information coming soon!
Boston Marathon
April 20th, 2026
We are excited to partner with five local champions in their efforts to run the Boston Marathon and support team CSIOBS. To learn more about the team and their journeys, click the link below.
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.
