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8 of the Most Fun Things to Do in Westchester in 2019


Photo by Andre Baranowski


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 three-course prix-fixe meals ($32.95 per person for dinner; $22.95 per person for lunch) to more than 250,000 diners.




Bicycle Sundays on the Bronx River Parkway

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 (a 6.5-mile stretch that runs from White Plains to Yonkers) for the exclusive use of joggers, cyclists, and walkers.




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.



Photo by Adam Sommer


Best of Westchester Party

Not to blow our own horn, industry-leading exhibitors, top-shelf food, illustrious guests, wall-to-wall media attention, music, dancing, 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. A record 34,000 reader ballots were cast in 2018, in addition to 120 editors’ picks, and 2019 is on track to break even those lofty benchmarks.




Yorktown Grange Fair

With classic fairground food offerings, nightly mainstage music, parades, carnival rides, midway games, blue-ribbon competitions, and livestock and produce exhibitions, this four-day event, founded in 1923, is billed as “Westchester’s Only True County Fair” for good reason. Attendees can also look forward to variety acts, hayrides, and a mile-long procession of vintage tractors, trucks and vehicles. This beloved annual excursion celebrates the historical traditions of agrarian Westchester better than any other, which is why it remains one of the most well-attended and joy-filled events in the region.



Photo by Jennifer Mitchell


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 that light up the night in a unique walk-through experience on the grounds of Croton-on-Hudson’s Van Cortlandt Manor. Past years have included such awe-inspiring sights and novelties as a pumpkin planetarium, flying pumpkin ghosts, and a giant pumpkin sea serpent. A more recent addition is the medieval castle, which is closely guarded by a parliament of jack o’lantern owls! Definitely one of the county’s most Insta-worthy events.





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. Sponsored by Historic Hudson Valley and eerily scored with live organ music, this show trots out iconic characters like the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel in the telling of a tale that is a perennial Halloween hit for young and old alike.




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 — which in recent years included acts like the Bruce Springsteen tribute band Tramps Like Us — in addition, of course, to the big guy himself, Santa Claus, in his new, interactive cottage home on Ridge Hill’s Market Street. Traditionally, Kacey, from WHUD’s “Mike & Kacey in the Morning,” serves as the evening’s emcee and introduces Santa as he makes his grand entrance, which culimantes with the countdown to the tree lighting.


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