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.
www.johnjayhomestead.org/events.html
Winter Extravaganza Baseball Card Show
One of the region’s largest shows for sports collectibles, this popular White Plains event features a range of autographed athletic memorabilia, vintage hobby boxes, and more baseball cards than you can shake a bat at.
www.nyshows.org/white-plains-show
The Great Westchester Train and Toy Show
Roughly 300 tables of new, used, and antique toys and trains come to White Plains during this annual affair. Kids and adults alike can pick up toy soldiers, die-cast cars, trains, tracks, and a wealth of other playthings.
www.westchestertoytrain.com
Annual Hudson River EagleFest
See some of the planet’s most impressive animals as Croton Point Park plays host to this annual event featuring hourly bird walks, close encounters with owls and eagles, and stage shows on everything from rearing raptors to backyard birding.
www.teatown.org/teatown-events/eaglefest.html
Big Brew Beer Festival
Leave the kids at home for this beer-fueled affair. More than 70 beer distributors converge on the Westchester County Center in February to offer 200+ different brews along with food,
music, and entertainment. Visit www.bigbrewny.com for additional dates and locations throughout the year.
St. Patrick’s Day Parades
Floats, bands, dancers, and a wide range of holiday-themed entertainers overtake Yonkers, White Plains, Mount Kisco, Sleepy Hollow, and Tarrytown during these annual parades.
Spring Westchester County Home Show
The largest and longest-running show of its kind in the region, this extravaganza of everything domestic features local, state, and national vendors presenting an assortment of home goods and household technologies in fascinating displays at the Westchester County Center.
www.jenksproductions.com/westches.html
Hudson Valley Restaurant Week
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Offered twice yearly for 14 days in March and November, this is the region’s largest dining event, with more than 200 participating restaurants offering bargain prix-fixe meals to more than 250,000 diners.
www.hudsonvalleyrestaurantweek.com
Lyndhurst Family Fun Day
Take your kids to this popular family event when the grounds of the Lyndhurst mansion are populated with amazing LEGO sculptures, moving displays, a play tent, petting zoo, and scavenger hunt.
www.lyndhurst.org/lego
Westchester Comedy Festival
Watch local comedians and celebrity headliners crack more than a few jokes at this festival, which takes place at a number of Westchester locales. Plus, a portion of the event’s proceeds go to benefit local nonprofits.
www.westchestercomedyny.com
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Crafts at Lyndhurst
Taking place in both September and April, this massive event includes 300 artists offering a range of one-of-a-kind gifts and artwork. Live music, kids activities, gourmet food, and craft demonstrations are also on hand.
www.artrider.com
Lightscapes
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Stare in awe as Croton-on-Hudson’s Van Cortlandt Manor erupts into an incredible nighttime display of sculptures, special effects, sounds, and state-of-the-art illumination. A bevy of spring-themed sweets and organic ice cream are also offered.
www.hudsonvalley.org/events/lightscapes
White Plains Outdoor Arts Festival
Peruse a variety of paintings, photographs, jewelry, textiles, ceramics, and glasswork for sale by a number of emerging and established artists. This event also features a free children’s arts-and-crafts table, as well as a host of unique food vendors.
www.whiteplainsoutdoorartsfestival.com
Caramoor Summer Music Festival
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Performers of classical, roots, jazz, and other music genres take the stage at this popular family-friendly event at Caramoor in Katonah. Taking place June through August, this festival features some of the nation’s biggest names in classical music.
www.caramoor.org
Related: 8 Must-Do Events of 2017
Clearwater’s Great Hudson River Revival
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There is something for everyone at Croton Point Park’s massive (its hosted more than 15,000 people) outdoor extravaganza, which includes seven stages of diverse music, dance, and storytelling along with clowns, jugglers, a children’s area, and a farmers’ market.
www.clearwaterfestival.org
Westchester Magazine’s Wine & Food Festival
The most inspired culinary event of the year comes to various locations throughout the area as Westchester Magazine holds its annual celebration of top edibles and fantastic wine and spirits. Enjoy the Burger & Beer Blast, Grand Tasting Village, An Evening with Westchester’s Tastemakers, and some of the very best eats in the region. www.winefood.westchestermagazine.com
Best of Westchester Party
Upwards of 3,000 guests come to celebrate the winners from Westchester Magazine’s annual Best Of issue at the beautiful Glen Island Harbour Club on the Sound Shore. A bounty of food and drink samples, spa and salon services, multiple bands, dancing, and more make this the Westchester party of the year.
westchestermagazine.com/Westchester-Magazine/Best-of-Westchester/Home/
Mamaroneck Firemen’s Carnival
The popular annual carnival leads up to Independence Day with parades and family-friendly activities. Beginning in late June, enjoy rides, games, a dunk tank, food, and raffles while raising money to support Mamaroneck’s Volunteer Fire Department.
Peekskill Riverfront Summer Concert Series
Big-name rock and country artists converge on Riverfront Green Park at this swinging concert series featuring fireworks, as well as numerous children’s specials.
www.peekskill.rocks
Pirates of the Hudson
This swashbuckling festival for all ages brings the trials and tribulations of pirates to vivid life with an engaging stage performance at the Tarrytown Music Hall.
www.hudsonvalley.org/events/pirates-hudson
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.
Moonviewing Concert
Celebrate the this time-honored Japanese tradition by wandering through a Japanese Stroll Garden lit by paper lanterns and enlivened by traditional Japanese musicians and a Japanese tea ceremony.
www.hammondmuseum.org
American Gold Cup
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Olympic-caliber horses and riders compete at this annual North Salem event where show jumping is the main attraction. There’s also boutique shopping and family fun, like pony rides, face-painting, and more.
www.theamericangoldcup.com
New Rochelle ArtsFest
Various locations in New Rochelle and Pelham play host to breathtaking performances by a range of dancers, singers, and entertainers, as well as numerous exhibitions, walking tours, and various other artistic events over this weekend celebration.
www.newrochellearts.org
Yorktown Grange Fair
With carnival rides, midway games, and livestock and produce exhibitions, this four-day event is one of the most well-attended and celebrated fairs in the region.
www.yorktowngrangefair.org
Armonk Outdoor Art Show
Nearly 185 artisans from across the county (and the country) exhibit at this annual, nationally recognized art show that showcases a variety of mediums, including painting, printmaking, jewelry, and photography.
www.armonkoutdoorartshow.org
The Great Jack O’Lantern Blaze
More than 7,000 individually hand-carved pumpkins light up the night in a unique walkthrough experience on the grounds of the Van Cortlandt Manor. Past years have included such awe-inspiring sights as a pumpkin planetarium, flying pumpkin ghosts, and a giant sea serpent.
www.hudsonvalley.org/events/blaze
Horseman’s Hollow
On selected evenings throughout the month, Philipsburg Manor brings The Legend of Sleepy Hollow to horrifying life with this haunted-house-style event featuring a frightening trail of terrors. Not recommended for children under 10.
www.hudsonvalley.org/events/horsemans-hollow
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.
www.yofifest.com
Stone Barns Center’s 14th Annual Harvest Fest
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A wide-ranging community celebration of life on the farm, 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.
www.stonebarnscenter.org/visit/harvest-fest.html
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.
www.tarrytownhalloweenparade.com
Westchester’s Winter Wonderland
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Get in the holiday spirit at Kensico Dam Plaza when this very merry extravaganza comes to town. 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.
www.wwinterwonderland.com
Valenti Thanksgiving Day Parade
Celebrating its 53rd year, this popular Thanksgiving Day Parade winds its way from North Avenue to Main Street in New Rochelle. Spectators can enjoy marching bands and various holiday-themed floats.
www.newrochellechamber.org/calendar-of-events
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.
www.armonkfrosty.com
Tree-Lighting Ceremonies
Experience the very best of what the holiday season has to offer when several Westchester towns (Katonah, Irvington, White Plains, and Yonkers among them) celebrate the lighting of their holiday trees. Many of the events offer various forms of refreshments, entertainment, and general merry-making.
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.
