Food & Drink Festivals to Check out in Westchester This Spring

Spring food festival season has arrived in Westchester! Start it off right by bookmarking these delicious happenings on your calendar.

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 4!

Bacon Fest

Down to Earth Ossining Farmer’s Market, Ossining
March 23, 9 a.m. – 12 p.m.

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Although you don’t need a reason to browse the stands at Down to Earth Farmer’s Market in Ossining, we have something that will make the trip a tad more worthwhile. The market will be giving out samples of sizzling hot juicy bacon courtesy of Goode & Local. Alongside the bacon will be breakfast treats from other vendors, plus complimentary Colombian coffee from 9 a.m. to noon, or while supplies last.

Taste of Dobbs Ferry

Sam’s Italian Ristorante, Dobbs Ferry
April 6, 2-8 p.m.

In honor of food, friendship, and mental health awareness, The Rivertowns Rotary Foundation and the JCK Foundation are hosting a foodie event. In the heart of Dobbs Ferry, guests will check in outside of Sam’s Italian Ristorante and make their way to Doubledays and Hudson Social. At each stop, guests will be able to indulge in the restaurant’s food, have a drink, get the opportunity to win prizes or raffles, and play games. The day wraps up with a live performance by The Slingshots. This event is dedicated to Scott Ritch, and all proceeds will go towards bringing the JCK Foundation Mental Health and Wellness Programs to Westchester communities in need. Tickets are $150 per person.


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Rosé Festival

Westchester Wine Warehouse, White Plains
April 18, 6-7 p.m

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Calling all rosé lovers! The ultimate wine experience awaits at the Westchester Wine Warehouse on April 18. At this event, you will discover the unique flavors and aromas of rosé wines from all over the world. Whether you’re a wine connoisseur or novice, there is always room to expand your knowledge and palate. This event will be hosted by experienced sommelier Olivier Flosse, and he will introduce you to a lineup of fascinating wines. The tasting will be held in a private tasting room.

Suds on the Sound Craft Beer Festival

Rye Town Park, Rye
May 11, 2-6 p.m.

Enjoy over 100 different craft beers from more than 50 breweries at the Suds on the Sound Craft Beer Festival on May 11. 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. Some participating breweries include Decadent AlesWolf & Warrior Brewing Co, Soul BrewingHudson North Cider, and much more. 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 4-8

Come on, how could we not say it? Finishing out the spring and kicking off summer, Westchester Magazine’s Wine & Food Festival is five days of non-stop decadence. This year we kick our signature food and drink festival off with a Wine Pairing Experience with Kevin Zraly. He will pair specialty wines with cuisine from Crabtree’s Kittle House Restaurant & Inn. Tickets are $155.

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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 will be our Sixth 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 $80.

On Friday, our Wine Collectors’ Dinner is being held at the 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 specially selected and prepared by Westchester’s top chef, Anthony Goncalves. Ticksta re $195 plus a minimum of one bottle of wine per person or one magnum per couple.

Everything culminates on Saturday with 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 the top restaurants. Tickets are $90 or $135 (Party Line Connoisseurs Tents).

Picks and Pickleball

Chilmark Village Park, Briarcliff
June 22, 12-5 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 from Captain Lawrence, a selection of divine food trucks, village vendors, and kids’ activities. Picks and Pickleball is presented by the Village of Briarcliff Manor and produced by River Towns Music Group. Click here for tickets and more information.

Related: 5 Marvelous Matcha Treats in Westchester County

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!

Our Best of Westchester Elimination Ballot is open through March 6!

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