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The Ultimate List of Fall Events in Westchester County

Find the festivals, special attractions, and unique features of fall in Westchester County here

By Kelly Fitzpatrick September 21, 2025

Are you looking for fall family fun in Westchester County? We have a round-up of the best places to visit with kids in our area. These fall attractions are special events taking place during the autumn months in Westchester County that your family is sure to love!

This guide is in the process of being updated with more fall family fun events.  Check back often as new events are added!


August 30th - November 2nd: Fall Festival at Outhouse Orchards, North Salem

September 6th - October 26th (weekends): Fall Festival at Harvest Moon, North Salem

September 23rd: Apple Cider Workshop at Westmoreland Sanctuary, Bedford

September 24th: Apple Picking and Stroller Workout at Stuart's Apple Farm, Granite Springs

September 27th - October 26th (weekends): Pumpkin Painting at Bedford Farms

September 27th: Sleepy Hollow Oktoberfest

September 27th: Apple Cidering and Fall Hike at Rye Nature Center, Rye

September 27th: Rocktoberfest at Matthiessen Park, Irvington

September 27th: Oktoberfest, Croton

October 2nd - 5th: Glass Pumpkin Fundraiser at Kingsland Point Park, Sleepy Hollow

October 3rd: Oktoberfest in Downtown Hastings

October 4th: Harvest Mess and Music Fest, Briarcliff Manor

October 4th: Pound Ridge Harvest Festival

October 4th: Peekskill Rotary's Fall Festival

October 4th: Fall Food Truck Festival in Memorial Park, Larchmont

October 4th: Scarecrow Making at Tarrytown Rec Office

October 4th: Cortlandt Family Fun Day at Cortlandt Youth & Rec Center

October 4th: Scarecrow Building at Harbor Island Park, Mamaroneck

October 11th: Fall Picnic at Greenburgh Nature Center, Greenburgh

October 11th: Fall Fest at Edith Read Wildlife Sanctuary, Rye

October 11th: Larchmont Day Fall Festival

October 11th: Scarecrows on the Sound, New Rochelle

October 11th - 12th: Oktoberfest at Cross County Center, Yonkers

October 11th - 13th: Pumpkin Picking at Muscoot Farm

October 12th: Falling for Fun Fest at The Sailhouse, Tarrytown

October 12th: White Plains Oktoberfest

October 18th: Fall Family Fun Event at Vassallo Park, Croton-on-Hudson

October 18th: Fall Foliage Festival at Broadway Field, Valhalla

October 18th: Fall Nature Walk at Jack Harrington Greenway Trail, White Plains

October 18th: Fall Fest at the Westchester Mall, White Plains

October 18th: Applefest at Boscobel, Garrison


Do you know of a family friendly event happening this fall in the Armonk, Chappaqua, Millwood, Mount Kisco, Thornwood, Pleasantville area and all the Westchester County towns in between? Submit it to our calendar and we’ll have it listed in no time!