On September 5, 2026, our community came together for the 22nd Annual 5K/2M Run-Walk for Education Fundraiser—and it was our biggest year yet! Approximately 300 runners and walkers filled the course, and the morning was full of energy, community spirit, music, food, and fun.

From the first runners to the final walkers crossing the finish line, every participant showed their dedication to supporting the students of the Ossining School District. It was a true celebration of community, unity, and a shared commitment to education.

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This year's race had a special hometown flavor: both overall winners were Ossining High School students! Emory Scheck took the overall men's title with a time of 18:48, averaging a 6:03-per-mile pace, while Kaya Wallace was the overall female winner with a time of 22:10, averaging 7:08 per mile. Congratulations to Emory, Kaya, and all our age-group champions for their outstanding performances! [View Race Results]

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A huge thank you to DJ Johnny G for keeping the crowd energized all morning, and to the dedicated community and school volunteers who handled registration, refreshments, water stations, course support, and everything in between. We couldn't do it without you!

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Another huge thank you goes out to Ron Whitehead and the wonderful Ossining High School photographers—Haley Druskin, Alex Tapia and Ossining grad Sam Raymond—who captured so many unforgettable moments throughout the morning. View Photo Gallery to relive the excitement of the day!

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Thanks to the incredible generosity of our sponsors, donors, and participants, we raised more than $37,000 this year, surpassing the more than $33,000 raised in 2025 and making this one of our most successful Run-Walks yet.​​

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These funds will directly support innovative programs, classroom resources, and educational experiences across the Ossining School District. Recent Ossining MATTERS-funded projects include new science equipment, calming spaces, book repair equipment, fitness center upgrades and physical education equipment, and opportunities for students to take part in robotics competitions, Science Olympiad, Business Club competitions, and environmental education aboard the Hudson River Sloop Clearwater.

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On behalf of the Ossining MATTERS Board of Directors, we extend our deepest gratitude to everyone who registered, sponsored, volunteered, donated, or helped spread the word. Your involvement means the world to us, and we look forward to continuing to achieve great things together!​​