These Are the Best Things to Do in Westchester All Through 2019

Before you know it, 2019 will be over, and we really want you to be able to say you had the "best year ever."


First Day Hike and Family Fun

The John Jay Homestead in Katonah hosts a day of family fun where kids can warm themselves by a roaring bonfire, sip hot cocoa, or take a scenic hike through the homestead’s sprawling grounds.



Annual Hudson River EagleFest

See some of the planet’s most impressive animals when Croton Point Park plays host to this annual event featuring hourly bird walks, close encounters with owls and eagles, and stage shows.



Spring Westchester County Home Show

The largest and longest-running show of its kind in the region, featuring an extravaganza of home goods and household technologies at the Westchester County Center.



Green Ossining’s Earth Day Festival

This free event at Waterfront Park is a celebration of sustainability, with 80-plus vendors, kids activities, craft beer, eco-demonstrations, and live music.


Lyndhurst Flower & Antiques Show

At this “wonderland of color and fragrance” on April 6 & 7, visitors may stroll the 67-acre park bedecked in stunning floral arrangements in guided tours or on their own. After, they may proceed to the boutique antiques show featuring singular items from top dealers.



Free Spirit Expo

Pay homage to Mother Earth in style at this holistic extravaganza on June 2.  The day-to-night event includes an immersive farm-to-table experience, lectures, workshops, artisan vendors, and live entertainment at Fable: From Farm to Table, in Ossining.  Be there and be renewed!


Rye Food Truck Festival

The Rye Recreation Center hosts its third annual Food-Truck Festival, attracting 12-plus food trucks from across New York and Connecticut. Previous participants have included MOC Eatery, LobsterCraft, Melt Mobile, Boxcar Cantina, Three Little Pigs BBQ, Waffle Box, and Walter’s Hot Dogs. The festival also has a kids’ zone and beer tent.


Westchester Magazine’s Wine & Food Festival

One of the most anticipated culinary events of the year hits locations throughout the area at this celebration of top edibles, wines, and spirits. Enjoy Burger & Beer Blast, Grand Tasting Village, and Westchester Tastemakers, among others.



Independence Day Celebrations

Expect live entertainment, refreshments, and lots of fireworks at these annual celebrations, which take place in locations throughout Westchester County, like Rye Playland, Kensico Dam Plaza, and Louis Engel Waterfront Park.


Pleasantville Music Festival

This annual crowd-pleaser features both national and local rock acts, myriad food vendors, a beer-and-wine garden, and a great vibe. Blues Traveler, Suzanne Vega, Gin Blossoms, Jakob Dylan, and Joan Osborne have all been featured in previous years.




Arthur Gonzalez workshop. _______________ #arthurgonzalez #sculpture #portchester #communitycenter #artworkshop

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Clay Art Center

They say clay is the new yoga, and the Clay Art Center on Beech Street in Port Chester has enough of the stuff on hand for its August adult-classes schedule to satisfy even the most prodigious potter. Skilled artist-teachers help students make their way through wheel-throwing, hand-building, and sculpture at a pace individualized to each student, with a variety of different techniques available to be learned.



Armonk Outdoor Art Show

More than 185 juried artists were on hand at the 57th annual  Armonk Outdoor Art Show. Hosted at North Castle Community Park, the event features a variety of art from around the world. Kids’ activities, food, and on-site parking available.


Photo by Elane Sommer

Apple Picking at Wilkens Fruit & Fir Farm

Wilkens offers apple, peach, and pumpkin picking daily from late August through mid-December. The bakery offers legendary apple-cider doughnuts, and a country market features gifts and local crafts. After Thanksgiving, Wilkens offers “choose-and-cut” Christmas trees from a variety of firs grown on the farm. Outhouse Orchards in North Salem and Stuart’s Fruit Farm in Granite Springs are other delicious apple-picking options.;;


Armonk Cider & Donut Festival

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


JazzFest White Plains

Now in its eighth year, this five-day extravaganza is for music lovers of all ages. Expect a covey of top-name artists and acts blanketing the city at various venues.


Yorktown Feast of San Gennaro

Everyone is Italian at this popular Yorktown event. In addition to predictably incomparable food and music, this festive five-day gathering offers arcade games, plush prizes, and a towering Ferris wheel.



New Rochelle ArtsFest

This free arts festival hosts a wide variety of  breathtaking performances by a range of dancers, singers, and entertainers, as well as exhibitions, tours, and other artistic events.


Stone Barns Center’s 15th Annual Harvest Fest

This yearly event features festivities for the entire family, such as live music, hands-on farming and food activities, hayrides, a turkey parade, and much more.



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Tarrytown Halloween Parade

The streets of Tarrytown take on a distinctly celebratory feel at this beloved yearly event that includes a massive parade, block party, live performances,
a DJ, and street-side dining.


Photo by Clifford Pickett

Jay Ghoul’s House of Curiosities

All-new in 2018, this popular annual Halloween event at atmospheric Lyndhurst takes you back to 1922 and a group of archaeologists who are dropping dead around a just-unearthed Ancient Egyptian tomb. Can you solve the crime before tragedy strikes again?


YoFi Fest: The Yonkers Film Festival

Get ready for four days of film at this annual event that takes place in various locations throughout Yonkers and includes screenings by emerging and acclaimed filmmakers, as well as kids movies, workshops, and nightly after-parties.


November - December

Frosty Day

One of the county’s most popular holiday traditions, this free event on Main Street in Armonk provides a firsthand glimpse of seasonal splendor with numerous activities and family events, including a grand parade featuring Frosty himself.


Holiday Parade & Tree-Lighting at Cross County Shopping Center

The Cross County Shopping Center in Yonkers hosts the first county tree-lighting event of the holiday season. The lighting of the 40-foot Christmas tree is only part of the annual tradition however: the night also features live music and a Holiday Spectacular Parade.


Westchester’s Winter Wonderland

Get in the holiday spirit at Kensico Dam Plaza. Kids can meet Santa Claus, enjoy unlimited rides on the Wonderland Express, and experience a musical light show. Refreshments, shopping, and ice-skating are also offered.



New Year’s Eve Celebration and Ball Drop

White Plains, Peekskill, New Rochelle (which celebrates New Year’s Eve at noon with a kid-friendly balloon drop) and other area towns and cities hold events ringing in the New Year with food, drink, music, and other attractions.


Tree-Lighting Ceremonies

Westchester towns like Katonah, Irvington, White Plains, and Yonkers, among others, celebrate the season with merry ceremonies. Many of the events offer refreshments and entertainment.



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