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

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

New Rochelle Arts Fest
Photo by Cristina Cerone

– January –

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.

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– February –

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.

– March –

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.

– April –

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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.

Japanese Cherry Blossom Festival

Welcome the spring in all its renewed glory at this annual event at Pelham Art Center that bursts with the vivid colors of Mother Nature at her best. In addition to the mesmerizing cherry blossoms, the event features a Japanese taiko drum performance and authentic Japanese dance numbers set to traditional music, as well as flower-arrangement and origami workshops for attendees of all ages.

Lyndhurst Flower & Antiques Show

Experience Tarrytown’s Lyndhurst mansion like never before for two days in April, adorned with stunning floral art arranged by local artists. Jewelry, garden ornaments, and other antiques are for sale, invite flower fanatics and families alike to explore this floral wonderland.

– May –

Bicycle Sundays on Bronx River Pkwy

One of Westchester’s longest-running recreational programs, this event on select Sundays in May, June, and September shuts down a portion of the Bronx River Parkway for joggers, cyclists, and walkers.


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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 March 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.

– June –

Caramoor Summer Music Festival

This popular family-friendly event features some of the nation’s biggest names in classical music at Caramoor in Katonah. Performers of roots, jazz,  classical, and other genres take the stage June through August.

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!

– July –

Best of Westchester Party

Not to toot our own horn, but with industry-leading exhibitors, top-shelf food, illustrious guests, wall-to-wall media attention, and upwards of 3,000 attendees, the annual Best of Westchester celebration at the majestic Glen Island Harbour Club is simply the county party of the year.

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.

Peekskill Riverfront Summer Concert Series

Six weeks of summer sunsets meet free musical performances at the picturesque Riverfront Green Park. From rock to pop to jazz, families are guaranteed to enjoy a night by the water each week, complete with food for purchase at nearby restaurants. Picnicking is also encouraged, if you can bear to stay seated.

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.

– August –

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.

Photo by Elaine Sommer

– September –

Apple Picking at Local Fruit Farms

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 popular 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, enough delicious doughnuts and fresh apple cider even the most ambitious fall tummy.

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.

Harvest Moon Farm & Orchard Fall Festival

Everything fun and fall converges in North Salem at the Harvest Moon festival each weekend in September and October. In addition to family-favorite farm activities, like hayrides and pony rides, attendees can pick their own apples and pumpkins on-site and enjoy seasonal treats. You’ll be awash in apple cider, cider donuts, and kettle corn, as well as the newest addition to the festival menu, specialty beer on tap from Hardscrabble Cider.

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.

Photo by Tom Nycz

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.

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.

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 Party on the Pier, among others.

Yorktown Grange Fair

With classic fairground food offerings, nightly mainstage music, parades, hayrides, carnival rides, and more, this multi-day event billed 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.

– October –

Jay Ghoul’s House of Curiosities

Now in its fourth glorious year, this eerie performance in Tarrytown brings Lyndhurst to life in a very different way (remember: The Dark Shadows movies used it as a location), with Halloween decorations, eerie lighting, and special appearances by the “Ghoul” family. Tour their home and meet those who haunt it during the weeks leading up to Halloween, or Halloween itself, if you dare. Parents and school-aged kids alike won’t want to miss this Halloween spooktacular.


The Old Dutch Church in Sleepy Hollow — made famous by none other than Washington Irving himself in “The Legend of Sleepy Hollow”— is the creepy setting of the newly expanded “Legend,” featuring master storytellers Jim Keyes and Jonathan Kruk. Eerily scored with live organ music, this show is a perennial Halloween hit for young and old alike.

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.

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, as well as live music and a lively parade.

Twinkling Lights on the Hill

From mid-November to New Year, Ridge Hill in Yonkers really decks the malls in this glitzy motif replete with all the yuletide regalia. Wide-eyed families are treated to magical light displays, carolers and other musical entertainment, in addition, of course, to the big guy himself, Santa Claus, in his interactive cottage home on Ridge Hill’s Market Street.

– December –

Chanukah City

The Festival of Lights overtakes Ridge Hill in Yonkers during this stirring annual event. On December 22, visitors can enjoy rides, music, seasonal refreshments, crafts, and entertainment, including a “gelt drop,” and the world’s first virtual-reality Chanukah experience. Not to mention a fun holiday train ride, balloon sculpting, 3D printing and robotics, as well as a kosher food truck. At the end of the day, kick back with a large-scale menorah lighting.

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.

Westchester’s 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.

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

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!

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