Party on the Pier at Playland: What to Expect at the Rye Food Fest

Here's what to know about the Wine & Food Fest boardwalk extravaganza, including food trucks and our annual Bartender Shake-Off. 

Start your summer strong with a trip to the beach with Westchester Magazine! Join us on Wednesday, June 5 for the signature Wine & Food Festival event, Party on the Pier at Playland Park in Rye. Experience the best that local restaurants and food trucks have to offer while overlooking the Long Island Sound as summer gets into full swing.

There will be food to satisfy all your taste buds. From traditional Italian offerings courtesy of Augustine’s Salumeria and Fortina to Southern fare from Crawdaddy’s Creole Kitchen and more, there will be a diverse and exciting variety of foods to try. Take the opportunity to explore and expand your culinary interests at any and all of the 30 featured vendors and restaurants.

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Don’t forget — there is always room for dessert at Party on the Pier! For those with a sweet-tooth craving, a donut from Duck Donuts or a scoop from Penny Lick Ice Cream will satisfy your sugary desires for starters, though there will be a limitless supply of sweet treats sure to induce a sublime sugar high.

To wash it all down, expect plenty of beer, wine, and cocktails for all. With a cool beverage in hand, experience the highly anticipated sixth annual Bartender Shake-Off, which features Westchester’s top bartenders competing for Best Bartender honors. Arrive around 6 p.m. and stay until 9 p.m. to ensure that you can experience a picturesque Long Island Sound sunset in Westchester. As the music plays in tune to the drinks that flow and the food that satisfies, the time is ideal for enjoying classic summer evening breezes off the water.


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Tickets to Party on the Pier are $65 and include all food and drink, with a discounted party pack option for groups of 10 available for $600. Gather up your friends and family for a night of delicious food and drinks, lively music, and a thrilling competition!

Related: This Westchester Wine Experience With Kevin Zraly Will Wow You

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Our Westchester Home Builders Awards take place on April 4!

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

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