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Westchester 2021 Fall Events Guide

by | Sep 21, 2021

Our Westchester guide offers a curated list of the best ways to enjoy Westchester County this fall. Join the community in admiring the beauty of the season and the culture within the county.

Click Here for the Full Westchester Fall Events Guide

Culture & Parades


Event Date: 10/8 – 10/24

Andrew Lloyd Webber’s remarkable life and career will be portrayed through stories and songs in this spectacular NY fall premiere.

Valenti Thanksgiving Day Parade

Event Date: 11/23, 10 AM

Nothing says Fall in New York more than a Thanksgiving Day parade! The city of New Rochelle hosts their 56th annual Thanksgiving Parade along North Avenue from Eastchester Road to Bonnefoy Place to celebrate the Thanksgiving spirit. Consider this a must-attend fall activity in New York!

Food & Markets

Westchester Wine & Food Festival

Event Date: 9/21 – 9/26

Experience the culinary spirit of Westchester at the Westchester Wine & Food Festival. Enjoy a week full of food trucks, award winning chefs, and exceptional wine and beer along with an exciting lineup of brand new events including an Italian Wine Experience with Kevin Zraly, Wine Collectors Dinner, Grand Tasting Village and more.

Heritage Applefest

Event Date: 10/6, 11 AM – 3 PM

The Heritage Applefest celebrates the bountiful harvest of the Hudson Valley with apple preserving, cider pressing, and cider tasting. Featuring Mark Rust, Daniel Stevens, and Penny Brickman, the entertainment at the Heritage Applefest will be the perfect setting to enjoy sweet cider doughnuts and delicious hard cider.

The Chocolate Expo

Indulge in your favorite goodies while enjoying entertainment and fun activities at the Chocolate Expo, the official home of chocolate, food, and fun!

Visual Arts

Westchester Craft Crawl

Event Date: 10/2 – 10/3, 11 AM – 5 PM

Westchester County hosts an outdoor fall events fair featuring several professional craft artists using many mixed media in their works, including clay, wood, metal jewelry, and glass.

ARRIVALS Exhibition Opening

Event Date: 10/2 – 10/3, 2:30 pm – 5 PM

ARRIVALS dives into remarkable American origin stories through an exploration of art and how creativity has shaped national mythologies. The ARRIVALS exhibit will be on view at the Katonah Museum of Art.

Click Here for the Full Westchester Fall Guide

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