8 of the Most Fun Things to Do in Westchester in 2021


At press time, some events and/or venues may have suspended operations or rescheduled due to the pandemic. Check with event sponsors and/or venues directly for the most up-to-date information.


– April –

Green Ossining’s Earth Day Festival

With a decade of successful outings under its belt, this free event at Louis Engel Waterfront Park emphasizes sustainability, environmental consciousness, and responsibility. Traditionally, Ossining’s Earth Day charms and disarms its attendees with a roster of family-friendly activities, including storytelling by Native American elders, a drum and ukulele circle, and eco-demonstrations. Plus, grab vegan food, craft beer, and eco-friendly products from on-site vendors.

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– May/November –

Hudson Valley Restaurant Week

Westchesterites and thousands of others in the region have been spoiled for many years by this can’t-miss biannual foodie event, held in May and November over 14 delicious days. Now under new management (meaning us!), you can expect more than 200 participating restaurants at this, the region’s largest dining event, offering irresistible deals on three-course prix fixe meals to more than 250,000 diners.

Photo by Gabe Palacio

– June –

Caramoor Summer Music Festival

This perennially popular, family-friendly event features some of the nation’s biggest names in classical music at the institution’s ethereal campus in Katonah. Performers of roots, jazz, classical, and other genres take the stage June through August, but Caramoor boasts great progamming four seasons a year.

Photo by Nik Bucci

– July –

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Pleasantville Music Festival

This world-class, annual crowd-pleaser rocks this otherwise sleepy, bucolic village with both national and local music acts, myriad food vendors, a beer-and-wine garden, and a great (zero-waste) vibe. Blues Traveler, Suzanne Vega, Gin Blossoms, Jakob Dylan, and Joan Osborne have all been featured in previous years.

Photo by Mike Dardano

– September –

Armonk Cider & Donut Festival

Sponsored by the Chamber of Commerce, family fun and health rule at this popular annual event held at Wampus Brook Park. The carnival honoring fall typically includes rides, live music, food trucks, a pie-eating contest, and doughnut fishing, along with a 5K run/walk, kids’ races, and, of course, enough delicious doughnuts and fresh apple cider to sate even the most ambitious fall tummy.

Photo courtesy of Taconic Marketing

– September –

Yorktown Grange Fair

With classic fairground food offerings, nightly mainstage music, parades, hayrides, carnival rides, and more, this multiday event — known among many locals as “Westchester’s Only True County Fair” — celebrates the historical traditions of agrarian Westchester. There is tons of fun to be had here, including a bubble-blowing contest and a rubber-chicken toss.

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Photo by Tom Nycz

– September – November –

The Great Jack-O-Lantern Blaze

Billed as “The Tri-State’s Biggest, Most Electrifying Fall Event,” the Jack O’Lantern Blaze showcases more than 7,000 hand-carved pumpkins on the grounds of Croton-on-Hudson’s Van Cortlandt Manor. Prepare to be greeted by such perennial favorites as the spell-casting witches, swooping jack o’lantern bats, humongous spider web, and mammoth sea serpent, among many other attractions. In 2021, the Blaze will hold its spin-off event, in Long Island’s Old Bethpage, for the second year.

Photo by Lauren Eisele

– December – January  –

Westchester Winter Wonderland

The holiday spirit is contagious at Kensico Dam Plaza, lit up each night with trees and other seasonal decorations. More than 100,000 people have enjoyed all-inclusive tickets since the event’s first season in 2014. There is no shortage of entertainment at this multiyear Best of Westchester winner, with unlimited holiday rides, outdoor ice-skating, circus performances, visits with Santa, and more. Attendees can purchase food and drink from food trucks and a full bar, and warm up inside heated tents.

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