Since the onset of Covid, Ossining MATTERS has held a "Movie by Moonlight" at Brookside Elementary School in Ossining. This annual event brings the community together for an entertaining evening under the stars. With food trucks and other vendors, this event will continue to be a staple in the community for a long time to come.

OM’s 5K Run/2 Mile Walk marks the beginning of the school year and is a major source of funding for the education foundation. Whether the sun is shining or the rain pouring down, it is always a fun community morning out for a relaxed stroll or a serious run.

Our shopping night is held annually, just in time for the holidays! In recent years, Holbrook Cottage has graciously hosted our event. The evenings have been a great time for friends to get together, enjoy some delicious fare and even do a little shopping. A percentage of the event’s proceeds has been donated to Ossining MATTERS enabling us to continue supporting enriching program throughout the school district. Thank you to Sue Taub and everyone at Holbrook Cottage for your continued generosity.

Our newest annual event is our Friendraiser/Soiree, which takes place on a winter Friday evening. This is a grown-up gathering open to all Ossining community members. This is a friendraiser, not a fundraiser; It’s a fun evening offering an opportunity to catch up with old friends, make new friends, and learn more about the education foundation. In past years, the Friend Raiser/Soiree was held at the Mike Risko Music School, 144 Croton Avenue, on January 25th from 7pm – 9 pm. If you were not able to join us, we hope you can next year!