Brought to you by The Georgio Reddington Team
There’s nothing quite like fall in the Sound Shore — crisp air, colorful leaves, and a full calendar of local events that bring our community together. From school fairs and art celebrations to charity runs and haunted attractions, autumn in Rye, Harrison, Larchmont, Mamaroneck, and Port Chester is a season to savor.
The Georgio Reddington Team is proud to live, work, and give back in this incredible community. Here’s a roundup of must-attend fall festivals and local happenings we’re thrilled to support (and in some cases, sponsor!) this season.
🏃♀️ Meals on Main Street 5K & Fun Run – Port Chester
October 19 | 8:30 AM | Starting at Colony Grill, Port Chester
Join The Georgio Reddington Team in supporting Meals on Main Street, a local nonprofit dedicated to fighting food insecurity across Westchester. This annual 5K & Fun Run brings runners, families, and neighbors together — all to help fund critical holiday meal programs for those in need.
This year, The Georgio Reddington Team is proud to be an official event sponsor, hosting some extra fun at the finish line! Stop by our tent for:
🎈 Balloon Artist
🎨 Face Painting
💪 Georgio Reddington Team Tattoos (temporary… but the spirit lasts all day!)
It’s a wonderful day filled with energy, community pride, and compassion — the kind of event that reminds us what makes the Sound Shore such a special place to call home.
👉 Register to run or donate — every step and every dollar makes a difference.
🎨 Rye City’s Annual Window Painting & The Monster Mural – Sponsored by The Georgio Reddington Team
October 20 | Downtown Rye | Purchase Street
One of Rye’s most beloved fall traditions returns! Students and families take over downtown storefronts for the Annual Rye City Window Painting Contest, turning Purchase Street into a colorful autumn art walk.
The Georgio Reddington Team is once again proud to sponsor the Monster Mural — a life-size community coloring wall outside Chase Bank on Purchase Street. Bring your kids, grab a marker, and help color this larger-than-life mural! It’s a joyful, creative celebration that perfectly captures the warmth and community spirit of downtown Rye in the fall.
🎡 Rye’s Osborn School Scare Fair
October 18 | Osborn School | 9:30am-2:30pm
Rye’s classic fall festival returns with carnival games, raffles, music, food trucks, and school spirit galore. The Scare Fair is a long-standing family favorite that brings together students, parents, and neighbors for an afternoon of fun and fundraising.
🧡 Mamaroneck’s Halloween Spooktacular
October 19 | Harbor Island Park | All Day
The fun begins with the Halloween Parade at 11:00 AM along Mamaroneck Avenue, leading right into Harbor Island Park where the celebration continues at 12:15 PM. Families can enjoy an afternoon full of trick-or-treating, crafts, games, pumpkin decorating, face painting, music from our DJ, and a spooky haunted house. Come dressed in your best costume and join us for a festive day of Halloween fun for everyone!
👻 Scared by the Sound at Rye Playland
Looking for something a little spookier? Head to Scared by the Sound, Westchester’s signature haunted attraction at Rye Playland. Open weekends through October, it’s perfect for thrill-seekers who love a good scare — right here on the Sound.
🛍️ Local Artisan Markets & Craft Fairs
Throughout October and November, local schools and community centers in Rye, Larchmont, and Harrison host weekend craft fairs featuring handmade gifts, décor, and delicious fall treats. It’s the perfect way to support local makers while getting into the seasonal spirit.