The Coolest, Tastiest Events You’ll Want to Hit Up This Week

We pick out 11 of the most entertaining ways to spend your off hours here in Westchester!

Welcome to one of the most exciting weeks of the season, Westchester Magazine’s Wine & Food Fest! Okay, okay, there are actually tons of events going on throughout the county, so we thought we’d bring you a few of the best, that way you can keep the whole family entertained and well-fed all week long!


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Wednesday, June 5

First up is a quick plug for all you shoppers in the 21-plus category: Following last night’s kick-off dinner and wine tasting, tonight is Wine & Food Fest’s Taste & Style event at Savor in The Westchester. The event includes tasty treats from some of the county’s best restaurants as well as participating deals, services, and raffles from the mall’s retailers, and our annual Bartender Shake-Off to determine the finest spirit singer around! Tickets are $30 and must be purchased in advance.


Thursday, June 6

Clear your schedules and your platters and put on your elastic-waist pants, it’s Burger & Beer Blast! Get ready to sample over 30 burgers from amazing local restaurants like 3 Westerly, Cooked & Co., X2O, The Whitlock, and reigning champions Coals Pizza! Can you make it through every one? Send us a video of you taking at least one bite of each and we’ll feature you in our coverage! Tickets are $75 online for unlimited food and beer, or $85 at the Kensico Dam gate.

Photo by Yu Matsui


Friday, June 7

Celebrate #FoodTruckFriday at our first-ever Food Truck Festival! We’re taking over the Cross County Shopping Center in Yonkers with more than a dozen local and regional food trucks serving up some sweet and savory bites alongside beer, wine, spirits, and enough live music to make this brand new bash one we’ll be sure to repeat. Tickets are $50 online of $60 at the gate.

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Saturday, June 8

If you’ve been sensing a theme here … Saturday is #WMwineandfood festival’s other biggest event, the Grand Tasting Village! Over fifty local restaurants and food trucks — plus numerous local vendors, sponsors, beer, wine, and liquor distributors — will be on hand back at Kensico Dam Plaza in Valhala to tempt you with the finest eatables and drinkables they have to offer. Tickets are $85 online or $95 at the door.



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Saturday also marks a couple of major charitable events in Westchester you might want to check out in addition to the charities benefiting from our Wine & Food Festival: The official Yonkers Relay for Life kicks off at Gorton High School at 3 p.m. Teams and partners have already raised over $80,000 of the event’s $100,000 goal, so stop by if you can and put them over the top!

Meanwhile in Northern Westchester, MLB icon Dwight “Doc” Gooden will be returning to the mound for a few innings of charity baseball between Yorktown’s 12U Sluggers and the Yorktown P.D. (Don’t worry, Doc’s pitching for the kids’ team!)

Also worth noting, Saturday marks the 39th Annual Ossining Village Fair! Enjoy even more live music, food trucks, a beer and wine garden, and fun kids and family activities, plus plenty of local vendors you can support.


Sunday, June 9

Close out your weekend with a bevy of local events to choose from. First up, because we’re shameless, is the Jr. Chef Experience where Westchester’s youngest food stars end Wine & Food Fest learning the basics from professionals including Chopped Jr. champions Elizabeth Oakes and sibling duo Arielle and Alfie Wayner! Tickets are $25 per child and include apron and toque.

For history buffs, The Slave Dwelling Project comes to Rye’s Jay Heritage Center this Sunday and will explore local spots that were once living quarters to American slaves. Yes, here in Westchester. The afternoon’s talks and tours are free and you can find more info on the event here.

Photo courtesy of the Bedford Playhouse

Local author Julie Satow will be visiting Bedford Playhouse for the release of her new book, The Plaza: The Secret Life of America’s Most Famous Hotel. The presentation and signing will go over some of the juicy details of the famed New York City landmark, and also feature brunch bites and either coffee of mimosa. Tickets are $25 with copies of the book available for purchase separately.

Finally, we end the evening on a light note with noted comedian and television host Seth Meyers dropping by The Ridgefield Playhouse at 9:30 p.m. Get there a little early to enjoy a tasting of local whiskey and gin from SoNo 1420 American Craft Distillers, then head into a set of raucous stand-up from the Late Nite host and SNL alum. Tickets are $90.

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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