August is almost over, which means Labor Day is right around the corner. After a summer of swimming, hiking, drive-in movies, and all the other warm-weather activities, it’s only fitting to cap things off with a Labor Day weekend to rival them all. From barbecues to bonfires and everything in between, the Hudson Valley is the perfect place to celebrate the end of summer as we transition into all the fall fun the region has to offer.
Columbia County Fair
Columbia County Fairgrounds, Chatham
August 28 – September 2
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One of the oldest continuing New York State fairs, the Columbia County Fair is back for Labor Day weekend. The six-day event celebrates 183 years of fun and community this year, with midway rides, animal and agriculture competitions, live music and comedy shows, a petting zoo, a circus, racing pigs, a demolition derby, and a rodeo. With something for everyone, the fair is fun for the whole family.
33rd Annual Hudson Valley Hot-Air Balloon Festival
Tymor Park, Union Vale
August 30 – September 1
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Now in its 33rd year, the Hudson Valley Hot-Air Balloon Festival offers a weekend of fun, including tethered hot-air balloon rides, full hot-air balloon flights, helicopter rides, fireworks, live music, food trucks, a beer and wine tent, local vendors, and a whole bunch of family-oriented activities to make your Labor Day weekend grand.
6th Annual Sunflower Festival
Barton Orchards, Poughquag
August 30 – September 2
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As the end of August brings sunflower season to the Hudson Valley, the bright yellow fields at Barton Orchards will certainly catch your eye this weekend. At the farm’s sixth annual Sunflower Festival, experience the life-sized flowers up close with a hayride through the five-acre field filled with 100,000 sunflowers, sample wine and beer, enjoy live music, hit up the farm market for local products, and bring the kids to the Fun Park.
Summer of Joy: Disco Summer Camp
Glen Falls House, Round Top
August 30 – September 2
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To close out Glen Falls House’s Summer of Joy, Disco Summer Camp makes its way to Round Top. Hosted by event producers Love Games and Chomp! Chomp!, the event includes four days of pool parties and late-night dancing in the tavern. Join others to dance the weekend away to the music of beloved DJs from Brooklyn and enjoy the day by hiking the grounds and exploring waterfalls as the summer comes to an end.
Woodstock-New Paltz Arts & Crafts Fair
Ulster County Fairgrounds, New Paltz
August 31 – September 2
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As a top arts and crafts show in America, the Woodstock-New Paltz Arts and Crafts Fair is a summer bucket list event in the Valley. At the fair, browse through hundreds of vendors and craftspeople working in numerous media, such as glass, wood, ceramics, metal, leather, jewelry, distilleries, healthcare products, and much more.
Woodstock Country Music Festival
Bearsville Center, Bearsville
September 1, 12–6 p.m.
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You’re invited to Woodstock’s first-ever Country Music Festival in Ulster County this Labor Day. The festival is hosted at the Bearsville Center and features four bands, including Way Behind the Sun, Tenbrooks Molly, The Bunkhouse Boys, and headliner Jake’s Rockin’ Country Band. If the music isn’t enough, food vendor CowGirls BBQ will be serving up smoked and barbecued meats, while handcrafted cocktails, nature trails, a vendor market, and free kids’ activities make the festival unforgettable.
Labor Day BBQ at Babblers Killside & Fireworks
Wylder Windham, Windham
September 1, 5–10 p.m.
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Wylder Windham has a lot to offer this Labor Day, from karaoke to fireworks. Spend the weekend at the Greene County resort to take part in activities like candle making, pickleball, dog contests, hatchet throwing, yoga, karaoke, and live music, or just stay on Sunday for a barbecue buffet at Babblers Killside and a fireworks show in the yard to celebrate summer’s end.
Good Ole’ Labor Day Bash
The Kartrite Resort & Indoor Waterpark, Monticello
September 1, 6–10 p.m.
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The Kartrite is known for family fun in Monticello, and Labor Day is no exception. The indoor waterpark and resort throws a barbecue at the onsite restaurant Eat. Eat. Eat., and outdoor activities like a pillow trampoline and paintball are the perfect end-of-summer thrills. Indoors, stay entertained all day long with a DJ, photo booth, blow-up ninja obstacle course, and more.
Labor Day Monday
Weed Orchards & Winery, Marlboro
September 2, 11 a.m. – 4 p.m.
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Apple-picking season has begun, and Weed Orchards & Winery is ready to celebrate the harvest season. For Labor Day, the farm’s café will be fully stocked with apple cider donuts and other goodies, while the trees are dotted with apples for you to pick and take home. Along with tractor rides and a playground for the kids, the holiday event is also perfect for dogs to tag along.
Related: Your Official Hudson Valley Apple Picking Farm Guide
