Westchester loves food. (We’ve seen what you like on our Instagram page, so you don’t have to deny it.) Now that the weather is finally turning milder, it’s time to bring that love out into the light of day for the most wonderful time of the year: food fest season!
Start making room now, and consult our handy calendar of upcoming food and drink festivals for all things eatable, drinkable, and thoroughly delicious. Don’t forget to grab tickets to our own Wine & Food Fest starting June 3!
Bacon Fest
Down to Earth Ossining Farmers Market, Ossining
May
Although you don’t need a reason to browse the stands at Down to Earth Farmers Market in Ossining, we have something that will make the trip a tad more worthwhile. The market plans on bringing back its Bacon Fest in May, and you won’t want to miss it. In previous years, the market gave out samples of sizzling hot, juicy bacon courtesy of Goode & Local. Follow the market’s Instagram to stay up-to-date.
Westchester Mac & Cheese Festival
Westchester County Center, White Plains
April 27, 1-5 p.m.
Do you love mac and cheese? Whether you love a classic bowl of cheesy goodness or you’re an adventurous eater, there’s a mac and cheese masterpiece waiting for you at this event. Participating restaurants include Chatterbox Restaurant & Bar, Tuck’d Away Bar and Grille, Bedford Hall Craft Beer and Kitchen Bar, and more.
Picks and Pickleball
Chilmark Village Park, Briarcliff Manor
May 10, 12-6 p.m.
This one-day food and drink festival celebrates some of the most important matters in Westchester: warm weather, live music, and pickleball. After participating in a friendly pickleball tournament, you can restore your energy with a pint of beer and a snack. This event will feature beer and wine, a selection of divine food trucks, village vendors, and kids’ activities. Picks and Pickleball is presented by the Village of Briarcliff Manor and Corcoran Legends Realty and produced by River Towns Music Group. This event is free for the whole family, while the pickleball tournament requires a fee.
Suds on the Sound Craft Beer Festival
Rye Town Park, Rye
May 10, 1 p.m.
Enjoy over 120 craft beers from more than 50 breweries at the Suds on the Sound Craft Beer Festival on May 10. Suds on the Sound is a celebration of craft breweries from all over the country that are enjoyed in Westchester on the Long Island Sound. Past participating breweries include Decadent Ales, Wolf & Warrior Brewing Co, Soul Brewing, and Hudson North Cider. The 2025 list is TBD. There will also be food trucks, live music, and vendors. For tickets and more information, click here.
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Westchester Magazine‘s Wine & Food Festival — June 3-8
Come on, how could we not say it? Finishing out the spring and kicking off summer, Westchester Magazine’s Wine & Food Festival is six days of nonstop decadence. This year, we kick our signature food and drink festival off with a ZWILLING Knife Skills Class. This hands-on class will teach you cutting techniques and what makes a quality knife. Tickets are $90.
Wednesday brings us Party on the Pier at Playland in Rye. Guests will enjoy a fun-filled evening on the Playland boardwalk overlooking the beautiful Long Island Sound while enjoying samples of summer favorites from local restaurants and food trucks plus beer, wine, cocktails, and music. The highlight of the night is the Seventh Annual Bartender Shake-Off, featuring Westchester’s top bartenders competing for Best Bartender honors. Tickets are $65.
Thursday ramps things up with our Burger & Beer Blast, which just keeps getting bigger with 30 local restaurants squaring off to see who has the best signature burger. Food trucks, local businesses, and plenty of libations and entertainment are also on the docket, as per usual. Tickets are $85.
On Friday, our Wine Collectors’ Dinner takes place at Kanopi in White Plains. This is the chance for all Wine Connoisseurs to tap into their collections and share their most valued vintages with other wine lovers. If you were holding back a bottle waiting for the right group to share it with, now is the time to pop that cork! This luxe showcase of unique vintages, which includes a champagne reception, will be an experience for every guest to taste and share the rare vintages that other guests bring from their cellars. Guests will also enjoy a memorable, one-of-a-kind dinner selected and prepared by Westchester top chef Anthony Goncalves. Tickets are $190 plus a minimum of one bottle of wine per person or one magnum per couple.
Saturday is our Grand Tasting Village, where more than 40 local restaurants and food trucks will serve up their best bites alongside more than 200 wine and spirits brands. There will be a private area featuring an exclusive lounge with the event’s highest quality wines along with dishes from top restaurants. Tickets are $90 or $140 for access to the Party Line Connoisseurs Tent.
Everything wraps up on Sunday with Boozy Brunch & Beats at Hudson Prime Steakhouse. Gather your friends and family for a one-of-a-kind brunch experience. Feast on bottomless mimosas, sangrias, and Bloody Marys while grooving to tunes spun by Top Notch Entertainment. Each table will have its own mimosa bar, and tickets cost $90.
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Related: 6 Speakeasies Serving up Serious Vibes in Westchester County
