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Labor Day Weekend in Dutchess County

Date Published: August 22, 2023

Labor Day is upon us, summer’s unofficial last hurrah, and if you’re planning a getaway this holiday weekend, you should come to Dutchess County. There are so many exciting things you can see and do here in the heart of New Yorks beautiful Hudson Valley to milk every last drop of fun out of summer and create memories that will last a lifetime. 

SplashDown Beach Water Park three slides with kids racing into the pool

Whether you’re an outdoor adventurer, a history buff or an artist — or even if you simply like breathtaking views — there are a million ways to enjoy the Hudson River right here in Dutchess. 

And that’s not all. 

We have an endless array of world-class dining options to satisfy every appetite. We have plenty of can’t-miss attractions for kids that will keep the fun rolling day and night. And don’t forget your four-legged friends -- we have lots of dog-friendly establishments and excursions here, too! There truly is something here for everyone (and when we say everyone, we mean everyone!). 

Here is a list of some Dutchess County events around which you can build an unforgettable road trip this Labor Day weekend. Keep that camera handy — click here to share your photos — and be sure to tag @dutchesstourism.com. 

Free Screening of “Strange Brew” at Hudson Valley Brewery 

Thursday, Aug. 31, 8 p.m. at Hudson Valley Brewery, Beacon  

Catch a free comedy at one of the region’s prominent purveyors of craft beverages, Hudson Valley Brewery. This Beacon operation specializes in colorful and unique sour IPAs, boasting beers with fun and quirky tasting notes (descriptors range from Gushers to coconut cream pie). Story Screen presents this outdoor screening of the Rick Moranis cult classic. 

Hudson Valley Hot Air Balloon Festival, Tymor Park, Union Vale
Hudson Valley Hot-Air Balloon Festival, Tymor Park, Union Vale

Hudson Valley Hot-Air Balloon Festival 

Friday through Sunday, Sept. 1-3 at Tymor Park, Union Vale 

See hundreds of colorful hot-air balloons rise over the largest town park in New York State. The 32nd annual Hudson Valley Hot-Air Balloon Festival offers dazzling sunrises, brilliant fireworks displays, live music, games, local food and one-of-a-kind balloon rides. To read all about the festival in our Spotlight blog, click here.

Cut Your Own Sunflowers at Barton Orchards’ Sunflower Festival 

Friday through Monday, Sept. 1-4 at Barton Orchards, Poughquag 

Hop on a fun-filled hayride which takes you to Barton Orchards’ blooming five-acre sunflower field. Hand pick from 11 varieties while listening to live music, sampling local craft beverages and tasting Hudson Valley products. If you’re coming with kids, be sure to take them to the fun park and petting zoo. Plus, there’s even a scenic orchard-side dog park for the family pooch. 

Millbrook Vineyards and Winery, Millbrook
Millbrook Vineyards and Winery, Millbrook

Food Trucks and Live Music at Millbrook Winery 

Friday, Sept. 1, 5:30-8 p.m. at Millbrook Vineyards and Winery, Millbrook 

Celebrate the start of the weekend with summer sunsets on the taproom terrace at Millbrook Vineyards and Winery. Eastern Dutchess County features gorgeous landscapes and natural vistas. Enjoy a picnic with dishes from local food trucks, ranging from empanadas and quesadillas to paninis and farm-fresh salads. Of course, don’t forget to sample award-winning wines produced onsite! 

FKAjazz Live  Performance  

Friday, Sept. 1, 8-10 p.m. at Habitas-on-Hudson, Staatsburg  

Habitas-on-Hudson kicks off the holiday weekend in style with a live performance featuring FKAjazz, the Grammy Award-nominated saxophonist and Billboard-charting music producer and DJ. Relax and unwind at this lavish countryside retreat and enjoy a genre-bending musical experience that fuses jazz, electronica, hip-hop and soul to create captivating rhythms, soul-stirring melodies and electrifying improvisations. 

Innisfree Garden, Millbrook
Innisfree Garden, Millbrook

Innisfree Garden's Hudson River Valley Ramble Birdwatching 

Saturday, Sept. 2, 9 a.m. at Innisfree Garden, Millbrook 

Visit one of the most stunningly unique destinations in the Northeast, Innisfree Garden. This curated landscape in Millbrook draws inspiration from centuries-old Chinese cup garden design. Join Kyle Bardwell, a seasoned wildlife photographer, for an early morning guided birdwatching walk. Many species use this diverse habitat (including a glacial lake) for breeding and migratory needs as they are on their way to wintering grounds. September sees a great number of warblers and songbirds passing through, and the garden is a perfect place to spot them. Then, stay for a picnic overlooking the stunning lake and take your time enjoying this peaceful place.  

Troutbeck, Amenia
Troutbeck, Amenia

Labor Day Barbecue at Troutbeck 

Sunday, Sept. 3, 12-3 p.m. at Troutbeck, Amenia 

Who could turn down a summer barbecue? Join the celebration at Troutbeck for a delicious communal meal in a breathtaking setting. Dr. Martin Luther King Jr., Langston Hughes, Ralph Waldo Emerson and Henry David Thoreau were among the many notable figures who stayed at Troutbeck as guests, seeking its tranquil beauty. A buffet-style lunch serves up such delights as Hudson Valley steelhead trout, charred summer squash steaks, farm-fresh ribeye, peach hand pies and a whole host of farm-fresh sides. The cost is $75 for adults and $35 for children. 

Northern Dutchess Symphony Orchestra with Craig Schulman 

Sunday, Sept. 3, 5:30 p.m. at Milea Estate Vineyard, Staatsburg 

Sample Milea’s heritage Hudson Valley wines and listen to heart-pumping Broadway showstoppers in Northern Dutchess County. Broadway veteran Craig Schulman, famous for his lead roles in “The Phantom of the Opera,” “Jekyll & Hyde,” and “Les Miserables,” performs iconic songs from his impressive career accompanied by the Northern Dutchess Symphony Orchestra. A cocktail hour preceding the concert is the perfect time to enjoy wines that can only be found here in Dutchess County, plus cuisine prepared by an alumn of The Culinary Institute of America. 

Related: CIA Chef Finder Pass 


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