7 Late-Summer Winery Events to Hit With Your Crew Near Westchester 

These wineries offer top-rated events throughout August and September. How many are on your bucket list? 

Hudson Valley wineries have become a staple in Westchester living, and we’re thrilled for this year’s lineup of music, food, events, and, of course, wine. Keep reading for a selection of events hosted at some of New York’s finest wineries, where you can sip and savor the flavors of the region.  

Warwick Valley Winery & Distillery

August 3-4, 24-25

With two weekend events coming up in August, country and rock music lovers will flock to Warwick Valley Winery & Distillery. First up, the Cash & Country Music Festival on August 3-4 brings iconic bands and New York whiskey vendors together. For rock fans, the Grateful Dead Tribute Concert, taking place on the weekend of August 24-25, offers a chance to relive music by the Grateful Dead. 

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Weed Orchards and Winery

August 3-4, 10-11, and 17-18 

There’s no better way to spend a weekend than by picking your own produce and sipping wine. On August 3-4, bring the family to the Peaches and Wine Fest. Look forward to picking fresh peaches and enjoying a variety of peach-themed foods and drink specials. Other events include the Taste of Summer Fest on August 10-11 with watermelon-themed drinks and the Taste of Summer Food Truck Fest on August 17-18, featuring local food trucks such as Empanada O’Nada, Pops Place, Just a Taste, and more.

Robibero Winery

August 17, 24 and September 21-22, 28-29 

Celebrate the 55th anniversary of Woodstock at Robibero Winery on August 17 from 11 a.m. to 6 p.m. Throughout the day, enjoy a mix of modern music and Woodstock-era music. Sport your tie-dye and colorful shades for a chance to win Robibero wine in the best-dressed contest. Following Winestock, next is the annual Seafood and Wine Festival on August 24. Enjoy hand-crafted wine paired with delectable offerings from Hooked Seafood. Enjoy amazing views, live music, prizes, and free games. VIP tickets are available, and admission is free for those 15 years of age and under. For two weekends in September (21-22 and 28-29), Robibero hosts the annual Grape Stomping Festival. The event includes grape stomping, a wine tasting, or one glass of wine or sangria.

 

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Millbrook Vineyards & Winery

August 25 

On August 25, join fellow winery enthusiasts for the Wine Run 5K. Starting at 10 a.m., race through the stunning scenery and landscape of Millbrook Vineyards & Winery. Both runners and walkers are welcome to participate. Registration includes a t-shirt, wine glass, finisher medal (which also serves as a bottle stopper), race bib, and a pour of wine.

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Brotherhood Winery

Events every weekend August 3 – October 13

Offering an exciting lineup of live music by Blank Canvas, Will Hinck, Mike Taylor, and more, Brotherhood is a must-visit for a weekend outing. Throughout September and into October, look forward to Grape Stomp weekends for an Instagram-worthy stage with wooden barrels set up for a fun competition. Grab a teammate to compete for a chance to win a special prize. There will be music and fun for the whole family. 

Bonus Wine-Themed Events Around Westchester  

Westchester Wine Walk & Craft Festival 

September 21 

Head to The Barley Beach House on September 21 to indulge in an afternoon of fine wine exploration. Sample a wide selection of reds, whites, roses, and more. There will be over 100 different wines from over 50 vineyards showcased. Also enjoy vendors selling hand-crafted items, food trucks, and live music. All participants will also receive a “Westchester Wine Walk” wine tumbler.  

13th Putnam County Wine & Food Fest 

September 21-22 

Hosted at Wells Park on September 21-22, the Putnam County Wine & Food Fest delights with samples of ciders, spirits, and wines from New York’s most renowned producers and beyond. Enjoy the last few days of summer by lounging on a blanket or lawn chair to enjoy savory foods and live music. There will also be arts and crafts, exhibits, and cooking demonstrations. 

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Related: Savvy Sips Wines and Spirits Uncorks a World of Flavor in Irvington

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