Eat, Drink, and Shop Local at These 5 Weekend Fests

An artsy market, two foodie fetes, and more from this week’s top picks for things to do in and around the Valley.


Dutchess County Fair

Dutchess County Fairgrounds, Rhinebeck
August 21-26

After a long year away, the Dutchess County Fair returns to Rhinebeck for its 173rd season. The festivities kick off on Tuesday with all the attractions, entertainment, and vendors that make the annual event unforgettable. This year, the Grandstand concert lineup includes The Wallflowers on Tuesday, Kane Brown (sold out) on Wednesday, Chris Lane on Thursday, and Kip Moore on Friday. The SporkRun food competition is back for its third year to judge the best bites on the fairgrounds. On Sunday, a free lumberjack show rounds out the weekend.

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Huichica Hudson Music Festival

Chaseholm Farm, Pine Plains
August 24-26

Huichica is a music festival, but it’s also much more than that. To complement its performance roster, the fest adds farm events like yoga on the lawn, milking at the barn, and tours of the farm to the schedule. Listen to artists like Bettye LaVette, Allah Las, and Hailu Mergia over the course of the three days. In between shows, take a break with a wine tasting and pizza lunch. Don’t forget to explore the vintage clothing “shops” onsite, too. 


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A past performance at Huichica Hudson Music Festival


Olana Summer Market

Olana State Historic Site, Hudson
August 25-26, 10 a.m. – 4 p.m.

Make this the weekend you finally check a visit to Olana off your summer bucket list. The former home of Hudson River School painter Frederic Edwin Church turns into a one-stop community venue over the course of Saturday and Sunday. Spend a day browsing the tables of local vendors, sitting in on crafty workshops, and snacking on treats from the area’s restaurants. When you need a break, throw down a blanket on the rolling grounds and enjoy the breathtaking Hudson Valley views.


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Putnam County Wine & Food Fest

Patterson Fire Department, Patterson
August 25-26, 11 a.m. – 5 p.m.

The Putnam party this weekend marks the return of the autumnal food and wine festival season in New York. Now in its eighth year, the Patterson event holds its own with an extensive list of local cideries, distilleries, and wineries, including Brotherhood Winery, Hillrock Distillery, and Salt Point Meadery. Regional artisans will showcase their wares onsite, while food stands and trucks like Three Little Pigs BBQ will feed the hungry crowd. Bring the kids to the children’s area and have a blast at the family-friendly event.


Grillsdale 2018

Roe Jan Park Hilltop Barn, Hillsdale
August 25, 2:30 p.m.

For its “Third Time’s A Char” celebration, Grillsdale brings together some of Columbia County’s top foodie professionals for a summertime hootenanny. Attendees can sip on drinks from Harney & Sons, Chatham Brewing, Irving Farm Coffee Roasters, and more while they sample bites from the culinary creators behind Lil’ Debs’s Oasis, The Copake General Store, and Yummy Kitchen, to name only a few. It’s bound to be a grilling good time.​​

Related: This Is How to Spend a Charming 24 Hours in Germantown

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