This guide is filled with fall fairs, festivals, events, and special happenings around Westchester County, outdoor activities, plus other ideas for things to do with kids.
Are we missing an event in or around Westchester County that you’d recommend to other families? Add it to our events calendar and it can be featured here, too!
This Guide to Westchester County Festivals and Fairs will grow throughout the season. Be sure to check back regularly so that we can help you to find your family fun.
This guide is brought to you by The Armonk Outdoor Art Show.
*Don’t forget to check the organization’s website for the most up-to-date details and notifications prior to attending.
Jump to: September | October | November | All Season Long
September Festivals, Fairs & Special Events |
*Don't forget to check the organization's website for the most up-to-date details and notifications prior to attending.
 D-Keine | Canva |
September 1st
Fall Festival at Outhouse Orchards
Pound Ridge Artisan & Vintage Market
September 6th
Simply Swifties Tribute at the White Plains Performing Arts Center
September 6th and 7th
Fall Festival at Outhouse Orchards
Flip Circus at the Jefferson Valley Mall
September 7th
Putnam County Feast of San Gennaro
HOOT Music Festival at Hudson Highlands State Park
Flip Circus at the Jefferson Valley Mall
NY Metro Reptile Expo at the Westchester County Center
September 13th and 14th
Septemberfest in Downtown Mount Kisco
50th Celebration Weekend at Muscoot Farm
Fall Festival at Outhouse Orchards
September 13th
Bedford Music Festival at Caramoor
September 14th
September 16th
National Play-Doh Day at Westchester Children's MuseumSeptember 16, 2025
September 20th and 21st
Fall Festival at Outhouse Orchards
Scarecrow Making Contest at Muscoot Farm
San Gennaro Feast at Railroad Park Commerce Street
September 20th
Herb Fair & Market at Caramoor
Magical Beasts & Where to Find Them: A Live Animal Event at Bedford Farms
September 21st
September 27th
Worldwide Day of Play at Mid-Hudson Discovery Museum
Rooted in Westchester: REV FEST 250
Chappaqua Children's Book Festival
September 27th and 28th
Fall Festival at Outhouse Orchards
September 28th
October Festivals, Fairs, and Special Events |
October 4th
Harvest Mess and Music Fest in Briarcliff Manor
October 11th
Fall Picnic at Greenburgh Nature Center
Check back soon!
November Festivals, Fairs, and Special Events |
Check back soon!
Fun in Westchester County All Season Long |
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Do you know of a family friendly event happening in the Westchester County area? Submit it to our calendar and we’ll have it listed in no time!
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