There’s something especially fun about fall along Westchester’s Sound Shore. The air turns crisp, the leaves blaze in amber and gold, and suddenly our charming streets of Larchmont and Mamaroneck begin to sparkle with the playful spirit of Halloween. It’s not just about costumes and candy — it’s about coming together as a community, celebrating tradition, and making memories that last well beyond October.
Larchmont’s Beloved Ragamuffin Parade
Every year, the Ragamuffin Parade reminds us why this community is so special. On Saturday, October 25th, families will gather around 2:00 PM along Larchmont Avenue between Palmer and Vanderburgh Avenues. The parade starts at 2:30 PM, filling the village with laughter, music, and the excitement of children proudly showing off their costumes.
When the parade reaches Constitution Park, the fun continues with DJ music, dance contests, storytelling, crafts, and yard games. Kids can visit the not-too-scary haunted house or pose for photos at one of the themed booths. Watching little ones light up with joy as they take in the sights is a reminder of how beautiful these small-town moments can be.
Local businesses decorate their windows, families stroll hand in hand, and the entire community joins in. It’s festive, it’s welcoming, and it captures everything we love about living here.
Mamaroneck’s Spooktacular Parade and Fall Festival
Just a few minutes away, Mamaroneck’s Spooktacular brings even more fall fun to the Sound Shore. This year’s event takes place on Sunday, October 19th, beginning with a lively parade at 11:00 AM in front of Smashburger on Mamaroneck Avenue. The parade ends at Harbor Island Park, where the real celebration begins.
Families can look forward to pumpkin decorating, crafts, games, face painting, trick-or-treating, and live music. The DJ keeps the energy up all afternoon while kids race across the park collecting treats and showing off their costumes. There’s even a haunted house for the braver ones, along with plenty of food and local vendors to enjoy.
Later in the month, Mamaroneck hosts a Haunted House and Outdoor Movie Night at Harbor Island Park. Bring a blanket, grab some popcorn, and settle in for a showing of Hocus Pocus under the October sky. It’s cozy, nostalgic, and perfect for families who love making the most of fall together.
Storybook Pumpkin Decorating Contest
On Monday, October 27th, the Mamaroneck Public Library invites kids ages 4–12 to bring their creativity to life at the Storybook Pumpkin Decorating Contest from 3:30 to 5:00 PM in the Community Room.
It’s a charming event where children pick the perfect pumpkin and paint it to resemble their favorite storybook character. Awards will be given for Most Creative, Best Character, and Funniest Pumpkin, judged by the Village of Mamaroneck Recreation Department.
What makes this event so special isn’t just the art, it’s the joy of seeing stories come alive through imagination. Parents and kids gather, laugh, and share the kind of simple happiness that defines what community really means.
Why These Traditions Matter
As someone who lives and works here, I’ve always believed that the true beauty of Westchester isn’t just in the homes we live in but in the people who fill them. Events like the Ragamuffin Parade and the Mamaroneck Spooktacular remind us that community is everything.
It’s the simple joy of seeing your kids run into friends on the street.
It’s neighbors greeting each other after a busy week.
It’s the laughter, the costumes, the shared excitement that makes this time of year so meaningful.
Halloween in Larchmont and Mamaroneck isn’t about perfection. It’s about showing up, celebrating together, and cherishing the little moments that make our towns feel like home.
From My Heart to Yours
Whether you’re a longtime resident or new to the area, I hope you’ll take a moment this season to enjoy all that our community has to offer. These events are a beautiful reminder of what makes living along the Sound Shore so special — connection, warmth, and a shared love for where we live.
Wishing everyone a safe, fun, and joy-filled Halloween. See you at the parade!
