Ossining Matters Run-Walk for Education Fundraiser

Join us for a morning of fun, fitness, and community!

Be part of a beloved local tradition at the 22nd Annual Ossining MATTERS 5K/2M Run-Walk for Education! Enjoy a scenic route heading north along the historic Old Croton Aqueduct Trail, with starting lines located in the heart of downtown Ossining on Main Street.

View the course map here.

It’s a morning filled with exercise, family, community spirit, and purpose—all in support of enhancing education for students in the Ossining School District. By participating, you’ll join hundreds of others in making a meaningful impact.

The mission of the Ossining MATTERS Education Foundation is to support and enrich the learning opportunities for all children in the Ossining School District. The goal of the foundation is to generate community awareness and support for the Ossining School District in order to provide an ongoing source of funds, through grants and other fundraising efforts, to augment the programs offered in the Ossining Public Schools. The funds will be used to develop and support programs in accordance with the Ossining School District’s mission statement in the areas of (but not limited to) academics, cultural arts, and athletics to ensure that each student realizes his or her fullest potential.

Special Participant Bonus!
Several of our generous Small Business Sponsors are offering exclusive incentives to race participants. These may include discounts, giveaways, or other perks when you visit their businesses. Be sure to check out the full list of participating businesses and their offers when you register today! Link to offers included in the registration confirmation email. 

Join fellow runners on September 5, 2026 for the Ossining Matters Run-Walk for Education Fundraiser. It's a fantastic 5K, 3.2K featuring a flat and fast course in Ossining.