38 Of This Year's Most Notable Events

January | February | March | April | May | June
July | August | September | October | November | December



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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. 

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.

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.

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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.

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Hudson Valley Restaurant Week

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.

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.

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.

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 offered.

Bicycle Sundays on the Bronx River Parkway

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


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.

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.

Caramoor Summer Music Festival

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.

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 everything edible. Enjoy the Burger & Beer Blast, Grand Tasting Village, An Evening with Westchester’s Tastemakers, and some of the very best eats in the region.

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.

Pleasantville Music Festival

This nonstop music-fueled weekend combines national acts and local up-and-coming bands from New York City and Westchester with famous food vendors, craft beer, positive vibes, play space for children, good friends, family, and charitable organizations.

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 including storytellers, magicians, and comedians.

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.

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.

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 50th anniversary of this annual tradition by wandering through a Japanese Stroll Garden lit by paper lanterns and enlivened by traditional Japanese musicians, as well as a demonstration of a Japanese tea ceremony.

American Gold Cup

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.

Jazz Fest

Including some of the country’s most talented jazz musicians, this multi-day event of performances takes place in multiple locations throughout White Plains, and features a wealth of food from area restaurants.

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.

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.

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.

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. Get tickets early, as this event sells out quickly.

Horseman’s Hollow

On selected evenings throughout the month, Phillipsburg 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.

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.

Stone Barns Center’s 13th Annual Harvest Fest

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.

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.

Westchester’s Winter Wonderland

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.  ?

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. 

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.

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 Years 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. 

Our CEOs & Business Leaders Golf Outing is August 5!

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

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!

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