
From the Organizer
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.
Events
Weather
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
78°
Typical Low
56°
Chance of Rain
28%
Based on US Climate Normals data from Yorktown Hts 1w, 7 mi from the venue.
Host City
City Elevation
244 ft
Nearest Airport
HPN
Westchester County Airport · 10 mi
Major Hub
LGA
LaGuardia Airport · 27 mi
Time Zone
Eastern Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
Your Next Start Line
Every finish line starts with a single decision. Claim your spot at 2026 Ossining MATTERS Run-Walk for Education Fundraiser, put it on the calendar, and turn “someday” into a start date.
80
Days to train
Coming Up
The 39th Annual Women's Distance Festival 5K
5 miles away
Nicky Cass 5k Challenge
5 miles away
Empire State Half Marathon & 5k
5 miles away
2026 Harry Chapin Memorial Run/Walk Against Hunger
3 miles away
From Endurance Grid
Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Frequently Asked Questions (FAQs)
2026 Ossining MATTERS Run-Walk for Education Fundraiser
Sep 5, 2026