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 top things off with a Labor Day weekend that’s on par with all the others. 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
28 August – 2 September
One of New York State’s oldest running fairs, the Columbia County Fair, is back for Labor Day weekend. The six-day event celebrates 183 years of fun and fellowship this year with rides, animal and agricultural competitions, live music and comedy shows, a petting zoo, a circus, pig racing, a demolition derby and a rodeo. The fair has something for everyone and is fun for the whole family.
33rd Annual Hudson Valley Hot Air Balloon Festival
Tymor Park, Union Vale
30 August – 1 September
Now in its 33rd year, the Hudson Valley Hot-Air Balloon Festival offers a weekend of fun including tethered balloon rides, hot air balloon flights, helicopter rides, fireworks, live music, food trucks, a beer and wine tent, local vendors and a whole host of family-oriented activities that will make your Labor Day weekend a great experience.
6th Annual Sunflower Festival
Barton Orchards, Poughquag
30 August – 2 September
Late August marks the start of sunflower season in the Hudson Valley, and the bright yellow fields of Barton Orchards are sure to catch your eye this weekend. At the farm’s sixth annual Sunflower Festival, you can get up close and personal with the life-sized flowers, sample wine and beer on a hayride through the 5-acre field of 100,000 sunflowers, enjoy live music, shop for local produce at the farmers market, and take the kids to the amusement park.
Summer of Joy: Disco Summer Camp
Glen Falls House, Round Top
30 August – 2 September
Wrapping up the Summer of Joy at Glen Falls House is Disco Summer Camp in Round Top. Hosted by Love Games and Chomp! Chomp!, the event includes four days of pool parties and late-night dancing at the tavern. Dance the weekend away with others to music from popular Brooklyn DJs, and enjoy the day hiking the grounds and exploring waterfalls as summer comes to a close.
Woodstock-New Paltz Craft Fair
Ulster County Fairgrounds, New Paltz
31 August – 2 September
One of the best arts and crafts fairs in America, the Woodstock-New Paltz Arts and Crafts Fair is a summer event that no trip to the Valley can miss. At the fair, you can visit hundreds of vendors and artisans working in a variety of fields, including glass, wood, ceramics, metal, leather, jewelry, distilleries, health products and more.
The Woodstock Country Music Festival
Bearsville Center, Bearsville
1 September, 12pm-6pm
You are invited to attend Woodstock’s first-ever Ulster County Country Music Festival on Labor Day. The festival takes place 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 offers smoked and grilled meats, while handcrafted cocktails, nature trails, a market and free activities for kids make the festival unforgettable.
Labor Day BBQ at Babblers Killside and fireworks
Wyld Windham, Windham
1 September, 5pm-10pm
Wylder Windham has plenty to offer this Labor Day, from karaoke to fireworks. Spend the weekend at Greene County Resort and take part in activities like candle pulling, pickleball, dog competitions, hatchet throwing, yoga, karaoke and live music, or just stay Sunday for a barbecue buffet at Babblers Killside and fireworks in the courtyard to celebrate the end of summer.
The good old Labor Day party
The Kartrite Resort & Indoor Waterpark, Monticello
1 September, 6pm-10pm
Kartrite is known for family fun in Monticello, and Labor Day is no exception. The indoor water park and resort hosts a barbecue at the on-site Eat. Eat. Eat. restaurant, and outdoor activities like a pillow trampoline and paintball are the perfect end-of-summer thrill. Indoors, you can be entertained all day long with a DJ, photo booth, inflatable ninja obstacle course, and more.
Labor Day (Monday)
Weed Orchards & Winery, Marlboro
2 September, 11am – 4pm
Apple picking season has begun, and Weed Orchards & Winery is ready to celebrate the harvest season. On Labor Day, the farm’s cafe will be packed with apple cider donuts and other treats, while the trees will be dotted with apples for you to pick and take home. In addition to tractor rides and a playground for the kids, the holiday event is also great for dogs who want to come along.
Related: Your official guide to the Hudson Valley Apple Harvest Farm
