2025 Evening Expedition Gala
Wednesday, November 5, 2025 | 6 PM
We hope you will join us at our 2025 Evening Expedition Gala on Wednesday, November 5, 2025. Our annual gala brings together over 300 corporate employees and local philanthropists from across Boston for an evening of celebration and community. Not only will you have the opportunity to expand your professional networks, but you will also get to meet many of the inspiring young people whose lives have been forever changed by the experiences and the magic they shared at Cathleen Stone Island Outward Bound School.
Tickets start at $500 and include access to dinner and a silent auction. Every dollar raised through this annual fundraising event will go directly toward supporting Cathleen Stone Island Outward Bound's core mission to build stronger, more equitable public-school communities through free experiential learning programs for Boston students.
Congratulations to the 2025 North Star Award Recipients, PwC!

The North Star Award is our opportunity to recognize extraordinary service and philanthropic efforts on behalf of Cathleen Stone Island Outward Bound School and the community we serve. Named for the star that has guided mariners across oceans for centuries, this award represents the guiding light of strength, integrity, and leadership, and its recipients embody and model these characteristics for all to benefit from.
We are thrilled to honor PwC this year for their long-standing commitment to CSIOBS through corporate sponsorship, Board and Committee leadership, volunteerism and grantors. PwC's support has ensured that we continue to offer hands-on science lessons and incorporate Outward Bound's best approach to social-emotional learning, leadership, compassion, and service for our Boston Public School students.
We offer 2025 North Star Award to PwC with deep gratitude for their dedication to Cathleen Stone Island Outward Bound School and our community, while looking forward to many more years of partnership!
Join Us!
Browse & Bid
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Not Able to Attend?
You can still participate in the auction!THANK YOU TO OUR 2025 SPONSORS!
Event Underwriter
THE DURANT FAMILY
Island Preservationist

Salt Marsh Restorer

Environmental Activist
AMALGAMATED BANK | CROWE, LLP | RYAN ENRIGHT | FISHER & PHILLIPS, LLP | KPMG, LLP. | LIBERTY MUTUAL
LOOMIS SAYLES & COMPANY | RAPDEV | U.S. BANK
Coastal Conservationist
MICHAEL DOUVADJIAN | ROBERT TISHMAN