January
First Day Hike and Family Fun
Get the new year started off on the right foot with a self-guided hike through the John Jay Homestead landscape. The day of family fun continues with a bonfire, hot cocoa, and a chance to browse the holiday shop’s end-of-season sale. johnjayhomestead.org/events
February
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. teatown.org/events/eaglefest
Young Artists Exhibition
The next generation of creators takes center stage at the Katonah Museum of Art’s long-running Young Artists exhibition. This perennial favorite showcases the work of local high school artists across the region from both public and private schools. katonahmuseum.org
April
Green Ossining’s Earth Day Festival
With more than a decade of success, the largest Earth Day Festival in Westchester keeps getting greener. Learn about sustainability, environmental consciousness, and responsibility through a roster of entertaining and family-friendly activities. Events include drum circles, beer tastings, a food foraging tour, learning how to eat sustainably, shopping from local and fair-trade artisans, and live music. greenossining.org/earth-day-festival
May
Bike Sundays on Bronx River Pkwy
A treasured recreational tradition since 1974, this program, on select Sundays from May through October, shuts down a 13.1 mile loop of the Bronx River Parkway for thousands of joggers, cyclists, and walkers. thewpf.org/bicycle-sundays
Hudson Valley Restaurant Week
Become a seasoned foodie in just two weeks at this can’t-miss spring/fall biannual event. Serving more than 250,000 dinners, it is the largest and most successful dining event in the region, with more than 200 participating restaurants. Treat yourself and the family to irresistible deals on three-course prix-fixe meals as you eat your way through the region. valleytable.com/restaurant-week
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! lyndhurst.org/events/spring-crafts
June
Caramoor Summer Music Festival
This family-friendly event features some of the world’s biggest names in music at Caramoor’s beautiful grounds in Katonah. From June through August, performers of American roots, jazz, classical, global music, and more take the stage at five venues on 80 acres. Plus, Caramoor boasts great programming year-round! caramoor.org
Prophet Elias Greek Festival
This big, fat Greek festival in Yonkers is a weekend celebration of all things Hellenic. Immerse yourself in Greek culture at Prophet Elias Church, with food, pastries, dancing, live music, and raffles. Prizes range from Michael Kors purses to smart TVs. facebook.com/GreekFestivalYonkers
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. westchestermagazine.com/wine-and-food
July
Best of Westchester Party
Join upwards of 3,000 attendees at the majestic Glen Island Harbour Club for the county party of the year. The annual Best of Westchester celebration brings together industry-leading exhibitors, top-shelf food, drinks and services, illustrious guests, wall-to-wall media attention, and more to celebrate the BEST the county has to offer. westchestermagazine.com/best-of-westchester-party
Pleasantville Music Festival
This world-class backyard bash brings together national and local music acts, myriad food vendors, a beer-and-wine garden, and a great (zero-waste) vibe. pleasantvillemusicfestival.com
Peekskill Riverfront Summer Concert Series
Running well into August, free musical performances meet gossamer summer sunsets at beautiful Riverfront Green Park. With each two-hour concert headlining a different genre, families are guaranteed to enjoy a night by the water each week, with food for purchase at nearby restaurants. cityofpeekskill.com/parks-and-recreation
Westchester Roots
Become immersed in the music and dance of other cultures without leaving the county. ArtsWestchester puts together a celebration of diversity across a variety of live music, dance perfomances, and festivals, all for free. artswestchester.org/westchester-roots
August
Clay Art Center
Clay Art Center on Beech Street in Port Chester has enough of the stuff on hand for its August adult-classes and family wheel nights 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. clayartcenter.org
September
Armonk Cider & Donut Festival
Kick off your fall festivities with this popular annual event held at Wampus Brook Park. After the morning 5K and kids’ races, the carnival typically includes rides, live music, food trucks, a pie-eating contest, doughnut fishing, and, of course, enough delicious doughnuts and fresh-pressed cider to sate even the most ambitious fall tummy. armonkchamberofcommerce.com
Armonk Outdoor Art Show
Ranked among the best arts-and-crafts shows in America, this family-friendly outdoor event descends upon our region each Fall 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. armonkoutdoorartshow.org
Harvest Moon 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, such as hayrides and pony rides, attendees can pick their own apples and pumpkins on-site and enjoy seasonal treats, including their specialty beer on tap, from Hardscrabble Cider. harvestmoonfarmandorchard.com
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. artswestchester.org/programs/jazz-fest-2
The Spirits of Sleepy Hollow Country: A Night of Legendary Magic
Long known as a spooky season destination, Sleepy Hollow is living up to its reputation with a new event at Philipsburg Manor. The Spirits of Sleepy Hollow Country: A Night of Legendary Magic features professional magicians Mark Clearview and Nick Wallace, who take visitors on a supernatural journey to conjure the spirits of Sleepy Hollow lore. Join Hulda, Major Andre, and the Headless Horseman for a night of mystery and fun. hudsonvalley.org/events/the-spirits-of-sleepy-hollow-country/
The 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. hudsonvalley.org/events/blaze
Stone Barns Center’s Annual Harvest Feast
Rain or shine, this yearly fundraising event for Stone Barns Center for Food and Agriculture features a one-of-a-kind outdoor meal experience. Visitors will learn about Stone Barns’ different growing spaces and systems and how everyone from farmers to chefs work together for an unforgettable day of food, fun, and sustainability. stonebarnscenter.org/feasts
Yorktown Grange Fair
With classic fairground food offerings, nightly mainstage music, parades, hayrides, carnival rides, and more, this multiday event — known among many as “Westchester’s Only True County Fair” — celebrates the historical traditions of agrarian Westchester. yorktowngrangefair.org
October
Irving’s Legend
Join master storyteller Jonathan Kruk for a spooky yet titillating evening as he performs the Halloween hit “The Legend of Sleepy Hollow” at Washington Irving’s Sunnyside. Enjoy the dramatic performance outdoors under the stars, in the company of the Headless Horseman himself. hudsonvalley.org/events/irvings-legend
Lyndhurst After Dark
Experience Gilded Age grandeur while exploring Victorian lore. Timed entry into the mansion allows visitors to walk through and soak up the spirit of the season on a semi-guided tour exploring the darker side of history through the lens of those who have inhabited the property. Visitors get a chance to experience the architecture, decor, and collection items on display while listening to the talented staff regale them about the traditions of the past. lyndhurst.org/events.
New Rochelle ArtsFest
This free arts festival and city-wide celebration hosts a wide variety of exhilarating performances by dancers, singers, and other entertainers, with exhibitions, tours, and family-friendly activites across 40+ venues. newrochellearts.org
Hudson Valley Restaurant Week
Become a seasoned foodie in just two weeks at this can’t-miss spring/fall biannual event. Serving more than 250,000 dinners, it is the largest and most successful dining event in the region, with more than 200 participating restaurants. Treat yourself and the family to irresistible deals on three-course prix-fixe meals as you eat your way through the region. valleytable.com/restaurant-week
November
LUMAGICA at Harvest Moon
At the end of November, Harvest Moon in North Salem dazzles for the holidays with this display of light sculptures, amounting to 750,000 LEDs. Life-size gingerbread people and animal sculptures are featured in the biggest holiday light park in all of Westchester and Putnam. The magical forest walking tour takes under an hour. Free parking. harvestmoonfarmandorchard.com/lumagica-light-show
Cross County Center
The Cross County Shopping Center in Yonkers hosts a tree-lighting event honoring the holiday season, as well as live music and a lively parade. crosscountycenter.com/events
Twinkling Lights on the Hill
From mid-November to New Year, Ridge Hill in Yonkers traditionally decks the malls in this glitzy motif replete with yuletide regalia. Wide-eyed families are treated to magical light displays, carolers, and other musical entertainment, with the big guy himself in his interactive cottage on Ridge Hill’s Market Street. ridgehill.com/events
Westchester’s Winter Wonderland
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. wwinterwonderland.com
YoFi Fest: The Yonkers Film Festival
Watch and learn at this celebration of all things film, located in the heart of the Yonkers waterfront. The festival features extensive screenings, a “mini film school” taught by industry professionals, and networking events for the entire film community. Not limited to big-screen feature films, this festival also airs shorts, documentaries, music videos, animation, pilots, and student work. yofifest.com
December
Frosty Day
Looking for some holiday fun for the whole family? This free event on Main Street in Armonk is one of the county’s most jolly holiday traditions. Get a firsthand glimpse of seasonal splendor with numerous activities and family events. Enjoy a series of live performances, face painting, hot cocoa and cookies, pictures with Santa, and a grand parade featuring Frosty himself. armonkfrosty.com
Holiday Parade & Tree-Lighting at Chanukah City
The wonderful Festival of Lights takes over Yonkers’ Ridge Hill, where visitors can enjoy rides, music, seasonal refreshments, crafts, and entertainment, including a “gelt drop,” and the world’s first virtual-reality Chanukah experience. ridgehill.com/events
New Year’s Eve Celebration & Ball Drop
White Plains, Peekskill, New Rochelle, and other area towns and cities hold events ringing in the New Year with food, drink, music, and other attractions.
Related: 6 Romantic Places to Propose Around Westchester County
