Toast: A Wine and Spirits Benefit

April 10, 2025

At Cathleen Stone Island Outward Bound, we challenge our students to try new things, and we're excited to offer the same opportunity for you! Join us for the 2025 Toast: Wine and Spirits Tasting Benefit.

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4K Trail Run

May 21 and May 22, 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 BBQ, unlimited beer and non-alcoholic beverages, and a sunset cruise back to downtown Boston.

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Fishing Invitational

June 17, 2025

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!

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Evening Expedition Gala

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 in the Fall and celebrate a year of learning, reflection and transformation for Boston students. 

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Boston Marathon Team & Falmouth Road Race!

Run for Team Cathleen Stone Island Outward Bound and support our mission of helping Boston youth learn, thrive, and grow through fundraising! We are proud partners of the 2025 Bank of America Boston Marathon Official Charity Program for the 5th year running, and plan to participate in the 2025 ASICs Falmouth Road Race for the 4th year in a row. Realize your dreams of running these historic races all while supporting Boston students!

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