Check out these can’t-miss events as you’re exploring the suburbs
Westchester was made for fall. From the crisp air to the colorful foliage and – our favorite – the amazing festivals and activities happening all across the county, this is an amazing time to visit and explore.
You can expect playgrounds packed with (potential) neighbors, local bands setting up under tents, school spirit everywhere, and small-business booths offering everything from apple cider donuts to artisanal crafts. These festivities reveal what daily life is like, and a great way to get a sense of what every fall could look like if you made a move. So grab your calendar and your favorite boots and let’s dive into what’s happening in Westchester this fall!
When: September 27‑28, 2025, Saturday and Sunday, 10:00 AM – 5:00 PM
Where: Armonk, NY (area showgrounds/business park)
What to Expect: Fine art, crafts, food & drink booths, a chance to explore local artists.
Chappaqua Children’s Book Festival
When: September 27, 2025, 10:00 AM – 4:00 PM
Where: Chappaqua Train Station
What to Expect: Author talks, illustrator appearances, a family fun zone, story times. Perfect if you’ve got kids who love books.
When: Saturday, September 27, 2025, 12:00 PM – 5:00 PM (Rain date: Sept 28)
Where: Constitution Park, Larchmont NY
What: Outdoor arts & crafts festival, local artists, music, and more.
When: Saturday, September 27, 2025, 2:00 PM
Where: Matthiessen Park, Irvington NY
What: Food trucks, music, a Kids Zone, and local bands.
Jay Day – Fall Family Festival
When: Sunday, September 28, 2025, 11:30 AM
Where: Jay Estate, Rye NY
What: Family-friendly festival, arts, crafts, and performances.
The Great Jack O’ Lantern Blaze
When: Now through November 16, 2025
Where: Van Cortlandt Manor, Croton‑on‑Hudson
What to Expect: Thousands of carved pumpkins lighting up the night with special effects, food and drink vendors, seasonal displays; a very popular immersive Halloween/fall spectacle. Great for families and photo ops.
Harvest Festival in Pound Ridge
When: October 4, 2025, 1:00 PM – 6:00 PM
Where: Pound Ridge Town Park
What to Expect: A classic autumn festival with food, music, children’s activities, and local vendors. Great family‑friendly feel.
Town of Mamaroneck Fall Food Truck Festival
When: Saturday, October 4, 2025, 11:00 AM – 4:00 PM
Where: Memorial Park, Larchmont NY
What: Food trucks gather in the park, casual gathering for families and neighbors.
When: Saturday, October 11, 2025, 11:00 AM – 3:00 PM
Where: Constitution Park, Larchmont NY
What: Live music, food & drink, face painting, petting zoo, pumpkin decorating, bounce houses, magic show, sack races, and a baking contest. Suggested donation: $10 per child age 2 and older.
When: October 11, 2025, 9:00 AM – 12:00 PM
Where: Pine Ridge Park, Rye Brook, NY
What: Pumpkin picking, games, children-friendly fall fun.
When: October 16‑26, 2025
Where: Lyndhurst Mansion, Tarrytown, NY
What to Expect: Evening tours of the historic mansion amid fall decor and candlelight; themed for Halloween season. Not a haunted house, but full of gothic atmosphere and architectural intrigue.
When: October 25, 2025, 10:30 AM – 12:00 PM
Where: Pine Ridge Park, Rye Brook, NY
What: Costumed pets, adoption meet-ups, fun events with animals.
When: October 29, 2025, 6:00 PM – 7:00 PM
Where: Pine Ridge Park, Rye Brook, NY
What: Community Halloween scene with decorated cars, treats.
When: October 5, 2025, 12:00 PM (Sensory Sensitive admission), 1:00 PM – 4:00 PM (General admission)
Where: Law Memorial Park Park, Briarcliff Manor, NY
What: This day of fun for children involves local music, LOTS of different types of sensory fun, and great food and goodies, too.
When: October 2025
Where: Bedford Village, Bedford Hills, Katonah
What: Three Westchester hamlets including Bedford Village (October 4th), Bedford Hills (October 5th), and Katonah (October 18th) are coming together to showcase the unique culture of the community. The art crawl will highlight artwork by local artisans, craftsmen, and visiting artists through different art forms (think pottery, photography, jewelry, and more).
When: November 15 – 16, 2025, 9:30 AM 5:30 PM
Where: Westchester Children’s Museum, Rye, NY
What: STEAM activities that celebrate the changing seasons for kids of all ages and learning or playing styles including Leaf Litter MicroBiomes, Pumpkin Batteries, DIY Corn Maze, Applesauce Cinnamon Dough Sculptures, Seed Sorting, and Leaf Raking.
When: Saturday, October 18, 2025
Where: Pelham Children’s Center, Pelham, NY
What: A fun-filled fall celebration for the whole family!
Ready to explore Westchester one fall festival at a time? We can help! Schedule your FREE initial strategy call and explore the NYC suburbs with the experts.
