As the Hudson Valley is home to an astounding number of wineries, there’s probably always something exciting happening at the vineyard. While it may be too hot to spend a day out in the fields in the summer, and winter often brings guests indoors, fall just so happens to be the perfect time to pay your local winery a visit. Dig into apple picking, food trucks, live music, and more at the region’s fall winery events this season.
Fizz Fest
Milea Estate Vineyard, Staatsburg
September 14, 12–6 p.m.
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Milea’s last party of the warm-weather season, Fizz Fest is all about sparkling wine and celebration as the vineyard introduces new releases and a sneak peek at its newest project. Along with new wines, catch some good vibes from the Jamaican Vybz Reggae band and enjoy special bites from the culinary team at the venue.
Weekend Food Trucks
Millbrook Vineyards & Winery, Millbrook
Saturdays & Sundays through October
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Millbrook Vineyards & Winery is no stranger to food trucks, and the destination is continuing its summer Food Truck Fridays series into the fall with Weekend Food Trucks. Stop by on Saturdays and Sundays throughout September and October for beautiful views from Millbrook’s picnic areas and taproom terrace, along with different cuisines from local food truck vendors.
Apples & Wine Fest
Weed Orchards & Winery, Marlboro
September 21-22, 28-29
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During peak apple picking weekends in the fall, Weed Orchards & Winery hosts its Apples & Wine Fest to ring in the harvest season. The fall winery event showcases Hudson Valley views, pick-your-own produce with multiple apple varieties available, and other family-friendly events like face painting, hayrides, and live music. End your day with Jane’s Ice Cream and apple cider donuts.
Grape Stomping Festival
Robibero Winery, New Paltz
September 21-22, 28-29, 11 a.m. – 5 p.m.
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Ever wanted to know how they actually make the wine? Give it a go yourself at Robibero Winery’s Grape Stomping Festival this September. The hands-on (or feet-on) experience includes grape stomping, wine tasting, live music, lawn games, and bonfires at the New Paltz hotspot. While at the vineyard, try the seasonal caramel apple sangria and delicious wood-fired pizza, too.
Out on the Farm
City Winery Hudson Valley, Montgomery
October 6, 1 p.m.
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City Winery Hudson Valley is big on outdoor festivals, bringing the summer vibes into fall with this all-ages upstate queer fall festival in Montgomery. Out on the Farm celebrates people from all walks of life as it also serves as a special adoption event in partnership with the Humane Society of Walden. Drag story hour, tractor rides, pumpkin picking, a farmstand, and guided wine tastings are just a few of the exciting activities planned for the event.
Fall Festival
Nostrano Vineyards, Milton
October 13, 11 a.m. – 5 p.m.
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An annual event at Nostrano Vineyards, the Fall Festival is back at the barn for its 10th year. Sip estate wines and wine cocktails and New York State craft beer, cider, and spirits, then browse a pop-up curated makers market, enjoy live music from Tony DePaulo, indulge in wood-fired pizza and other local eats, and have fun with the family at kid-friendly activities for an admission of just $10 per person.
Halloween Ball
Brotherhood Winery, Washingtonville
October 26, 7–11 p.m.
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It’s never too early to lock in your Halloween plans in the Valley, especially when they could be at America’s oldest winery. Brotherhood throws its annual Halloween Ball on October 26 for a creepy night of unforgettable thrills and fun. Drink wine, enjoy a lavish buffet, dance the night away, and come in the best costume to be awarded wine bottles to take home.
Related: The Best Apple Cider Donut Destinations in the Hudson Valley
