7 Must-Do Events in Westchester County Throughout the Year

Check out these must-do events in Westchester. Adobe Stock

From antiques, art, and flowers to our own wine and food festival, here are some of the hottest things to do in Westchester County.

Check with event sponsors and/or venues directly for the most up-to-date information.

Spring must-do events
Courtesy of Lyndhurst, A Site of The National Trust For Historic Preservation


Spring Crafts at Lyndhurst

Peruse the unique creations of more than 200 craftspeople and makers during this annual show overtaking the scenic grounds of Tarrytown’s Lyndhurst mansion each spring. The family-friendly event features jewelry, handmade fashions, sculptural works, prints, paintings, photographs, and more, along with gourmet foods, food trucks, and tastings from local wineries, distilleries, and cider houses. What’s more, they do it all again in the fall!

Wine and Food Fest
Photo by Ed Shin


Westchester Magazine’s Wine & Food Festival

After more than a decade of success, this 21-and-over event remains one of the most anticipated culinary occasions of the year. Travel to multiple locations throughout the area for a celebration of more than 100 top edibles, wines, and spirits. Enjoy Burger & Beer Blast, Grand Tasting Village, and Party on the Pier, among others.

- Advertisement -
jazzfest must-do events
Photo by Mehdi Hassine/ courtesy of ArtsWestchester


JazzFest White Plains

Calling all jazz cats! After more than a decade of toe-tapping performances, this beloved five-day celebration of jazz, presented by White Plains’ ArtsWestchester, continues to attract music lovers of all ages. Expect a covey of top-tier artists and rising stars lighting up the city at a variety of venues.

pumpkin blaze must-do events
Photo by Tom NYCZ/ Courtesy of Historic Hudson Valley

– September to November-

Great Jack O’Lantern Blaze

Celebrate the spooky season in style during this annual event embracing all things pumpkin. Fall in Westchester wouldn’t be complete without a visit to this Halloween extravaganza, which overtakes the grounds of Croton-on-Hudson’s Van Cortlandt Manor with roughly 7,000 hand-carved, illuminated jack-o’-lanterns in a dizzying array of forms — from a pumpkin carousel and an immersive river display to a recreation of the New York City skyline — all enlivened by synchronized lighting and a ghostly original soundtrack.

art show
Photo courtesy of Armonk Outdoor Art Show


Armonk Outdoor Art Show

Ranked among the best arts-and-crafts shows in America, this family-friendly outdoor event descends upon our region each spring with a veritable tsunami of paintings, prints, sculptures, drawings, pastels, photography, fine art, and so much more. With everything for sale in an open-air environment, past years have included food vendors, drinks, and a tent where there are free activities for kids.

winter must-do events
Photo courtesy of The Westchester Parks Foundation

-November to January-

Westchester’s Winter Wonderland Drive-Thru Extravaganza!

There’s no better way to feel the holiday spirit than with Westchester’s Winter Wonderland. In 2020, this all-out-immersive holiday experience became a 1.2-mile-long, drive-through-only event, with a host of eye-popping lights displays, including a 40-foot Christmas tree, 50-foot illuminated dove, and 100-foot light tunnel, along with dancing trees, glowing snowballs, and Candy Cane Lane. Bid a warm hello to host elves Ned & Albert.

february must-do events
Photo Courtesy of Teatown


Teatown Hudson River EagleFest

Soaring eagles take centerstage during this popular outdoor occasion at Ossining’s Teatown Lake Reservation. Bird lovers are invited to keep their eyes to the sky as they enjoy snacks and hot beverages for sale, scoop up some high-flying, bird-related merchandise, or catch a presentation.

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.