Ossining MATTERS

09/01/2026

🏃 THIS SATURDAY IS THE DAY!

The wait is almost over! This Saturday, September 5, Ossining comes together for the 22nd Annual Ossining MATTERS Run-Walk for Education! 🎉

Whether you’re running the 5K, walking the 2-mile course, or coming out to cheer, your participation helps support educational opportunities for students throughout the Ossining School District.

📅 Saturday, September 5
⏰ 8:00 AM
📍 Joseph G. Caputo Community Center

Haven’t registered yet? There’s still time!

👉 Register now at www.OssiningMATTERS.org

Grab your family, friends, and neighbors and join us! ❤️🖤
Every mile makes a difference!

08/31/2026

🥋 Sponsor Spotlight: UMAC Briarcliff

We’re proud to recognize UMAC Nation as a Trail Marker Sponsor of the 22nd Annual Ossining MATTERS Run-Walk for Education!

UMAC Nation helps children, teens, and adults build confidence, discipline, focus, and healthy habits through martial arts, while creating a supportive community for families.

We’re grateful for UMAC Nation’s support of Ossining students and educational opportunities! ❤️🖤

🏃 22nd Annual Ossining MATTERS Run-Walk
📅 Saturday, September 5, 2026
⏰ 8:00 AM
📍 Joseph G. Caputo Community Center

👉 Register today: www.OssiningMATTERS.org

Thank you, UMAC Nation, for helping us make every mile count!

08/31/2026

Get ready for the 22nd Annual Ossining MATTERS Run-Walk on Sept 5!

Don't miss important details shared in our latest email to registrants, including a location change for bib and packet pickup.

***We encourage everyone to register online at www.ossiningmatters.org before the event to avoid long lines and wait times on the morning of.***


https://conta.cc/4gs0j4d

Email from Ossining MATTERS 5K/2M Run-Walk - Sept. 5, 2026 Hello Registrant! We’re excited to see you on Saturday, September 5, 2026, for the 22nd Annual Ossining MATTERS Run-Walk for Education! Here

08/30/2026

❤️ Small Business Sponsor Spotlight: Westchester Stationery

We’re excited to recognize Westchester Stationery as a Small Business Sponsor of the 22nd Annual Ossining MATTERS Run-Walk for Education!

A longtime Main Street Ossining staple, Westchester Stationery is a neighborhood shop known for friendly service, everyday essentials, and its popular breakfast offerings. We’re grateful for their support of our community and, most importantly, Ossining students! Westchester Stationery

🏃 Saturday, September 5, 2026
⏰ 8:00 AM
📍 Joseph G. Caputo Community Center

👉 Register today: www.OssiningMATTERS.org

Thank you, Westchester Stationery, for helping us make every mile count! ❤️🖤

08/29/2026

🎉 ONE WEEK TO GO! 🏃‍♀️🏃‍♂️

The countdown is on—just ONE WEEK until the 22nd Annual Ossining MATTERS Run-Walk for Education! 🎉

Join your friends, neighbors, students, teachers, and families as we kick off the school year with one of Ossining's favorite community traditions.

Whether you're running the 5K, walking the 2-mile course, or cheering from the sidelines, every step helps fund innovative educational opportunities for students across the Ossining School District.

📅 Saturday, September 5, 2026
🕗 8:00 AM
📍 Joseph G. Caputo Community Center

🎶 Live Music
🏅 Finisher Medals
🎟️ Raffles
🍎 Refreshments
❤️ Community Spirit

There's still time to register!

👉 Register today at www.ossiningmatters.org

Let's make this our biggest and best Run-Walk yet. We can't wait to see you at the starting line!

08/28/2026

🏡 Small Business Sponsor Spotlight: GuardHill Financial

We’re proud to recognize GuardHill Financial as a Small Business Sponsor of the 22nd Annual Ossining MATTERS Run-Walk for Education!

With more than 30 years of experience, GuardHill specializes in residential mortgage financing, providing personalized guidance and customized solutions to help homebuyers and homeowners achieve their goals.

We’re grateful for GuardHill’s support of Ossining students and educational opportunities! ❤️🖤

🏃 Saturday, September 5, 2026
⏰ 8:00 AM
📍 Joseph G. Caputo Community Center

Register today: www.OssiningMATTERS.org

Thank you, GuardHill, for helping make every mile count!

08/27/2026

🦷 Sponsor Spotlight: Briarcliff Pediatric Dentistry 😁

A healthy smile and a strong community go hand in hand!

Thank you to Briarcliff Pediatric Dentistry for supporting the 22nd Annual Ossining MATTERS Run-Walk for Education as a Small Business Sponsor.

Your generosity helps expand educational opportunities for students throughout the Ossining School District, and we're grateful to have you as part of our Run-Walk family.

📅 Saturday, September 5, 2026
📍 Joseph G. Caputo Community Center

👉 Register today at www.ossiningmatters.org

Thank you for helping our students smile a little brighter!

08/26/2026

🎉 Sponsor Spotlight: Kiddie Academy of Briarcliff Manor ❤️

We’re excited to recognize Kiddie Academy of Briarcliff Manor as a proud sponsor of the 22nd Annual Ossining MATTERS Run-Walk for Education!

Kiddie Academy is dedicated to providing children with a nurturing, engaging learning environment where they can build confidence, curiosity, creativity, and a strong foundation for future success. 📚✨

We’re grateful for their support of Ossining MATTERS and their commitment to helping children and families in our community thrive!

📅 Saturday, September 5, 2026
🕗 8:00 AM
📍 Joseph G. Caputo Community Center

Join us for the 5K or 2-mile walk and help support innovative educational opportunities for students across the Ossining School District!

👉 Register today at https://runsignup.com/Race/NY/Ossining/OssiningMATTERSRunWalkFundraiser

Thank you, Kiddie Academy of Briarcliff Manor, for helping make a difference in the lives of local children! ❤️

08/25/2026

🎸 Sponsor Spotlight: School of Rock Briarcliff Manor 🎶

Let's hear it for School of Rock!

We're proud to recognize School of Rock as a Small Business Sponsor of the 22nd Annual Ossining MATTERS Run-Walk for Education.

Their support helps create opportunities that inspire learning, creativity, and success for students across the Ossining School District.

Thank you for helping our community hit all the right notes!

📅 Join us on Saturday, September 5, 2026
📍 Joseph G. Caputo Community Center

👉 Register today at www.ossiningmatters.org

08/24/2026

🎉 Sponsor Spotlight: Leg. Emiljana Ulaj 💙

A heartfelt thank you to Westchester County Legislator Emiljana Ulaj for supporting the 22nd Annual Ossining MATTERS Run-Walk for Education as a Small Business Sponsor!

Her commitment to our community and support for educational opportunities help make a meaningful difference for students throughout the Ossining School District.

We are grateful for her partnership in helping us fund innovative programs that inspire learning, creativity, and success.

📅 Saturday, September 5, 2026
📍 Joseph G. Caputo Community Center

👉 Register today at https://runsignup.com/Race/NY/Ossining/OssiningMATTERSRunWalkFundraiser

Thank you, Legislator Ulaj, for investing in the future of our students!