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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 York's beautiful Hudson Valley to milk every last drop of fun out of summer and create memories that will last a lifetime.
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 activities 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 on social media.
• Ride the waves and soak in the fun at SplashDown Beach Water Park in Fishkill — "America's Biggest Little Water Park!" Get your adrenaline pumping on The Megalodon raft ride or the Humunga Half-Pipe (New York’s only zero-gravity half-pipe). Cool off and catch your breath as you float down the Croc Creek Wavy Lazy River in your own tube. The Pelican Bay Water Playground features four water slides and a 500-gallon dumping bucket, while the Shipwreck Lagoon is perfect for the little tots. Plan ahead and check out their incredible deals on 2025 season tickets!
• Safely take a dip in the mighty Hudson River at The River Pool in Beacon. This floating circular pool is located off the north shore of Pete and Toshi Seeger Riverfront Park and is free to use. It is secured to the river bottom and enclosed in netting so people can safely walk on the pool floor without touching the river bottom or vegetation. Swimmers can sit, float and play under the watchful eyes of an on-duty lifeguard. The pool rises and falls with the tide so it maintains a constant depth of 24 to 30 inches.
• Of course, no kid-friendly summer excursion would be complete without some ice cream, and here in dairy-rich Dutchess County, we take pride in our locally crafted flavors. Check out our guide to the Top 10 Places to Get Ice Cream in Dutchess.
• See hundreds of colorful hot-air balloons rise over the largest town park in New York State. The 33rd annual Hudson Valley Hot-Air Balloon Festival (Aug. 30–Sept. 1) 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.
• Get a bird's-eye view of the Hudson River and surrounding highlands with a flight in an authentic, open-cockpit biplane at the Old Rhinebeck Aerodrome in Red Hook. The Aerodrome hosts antique air shows every Saturday and Sunday through Oct. 20. The Saturday "History of Flight" program highlights the Pioneer Era before World War I and the Golden Age of Aviation in the 1920s and 30s. The Sunday air show is the World War I dog-fight spectacular, with a hero or heroine, the villainous Black Baron of Rhinebeck, scenery, pyrotechnics and a World War I tank, along with many antique automobiles. There are usually between 15 and 20 flyable aircraft for each show.
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• Barton Orchards’ sixth-annual Sunflower Festival (Aug. 23–25 and Aug. 30–Sept. 2) features all sorts of fun for the whole family! Hop on a fun-filled hayride which takes you to their 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.
• The sunflower blooms are bountiful and beautiful during the seventh-annual Sunflower Cutting Season at Hudson Valley Cold Pressed Oils in Pleasant Valley. The fields are open in the evening on Fridays, Saturdays and Sundays through Sept. 1. Enjoy live music, food and beverages while you pick!
• Labor Day Weekend should be prime picking season for apples in the Hudson Valley at places like Barton Orchards in Poughquag; Cedar Heights Orchard in Rhinebeck; Dykeman Farm in Pawling; Fishkill Farms in Hopewell Junction; Greig Farm in Red Hook; Mead Orchards in Tivoli; Meadowbrook Farm in Wappingers Falls; and Rose Hill Farm in Red Hook.
• Can't make it out to the farm? Stop by one of these farmers markets in Dutchess County for fresh fruits, vegetables and flowers, meats and cheeses, and a bevy of locally crafted products.
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• Guitarist Nicky Barbato is the headlining act on Aug. 31 in the popular Sunset Music Series at Plan Bee Farm Brewery in Poughkeepsie. Enjoy the show on the Farmstand Stage, which features a mural by artist Natalie Renganeshi that is designed to change visually with the setting sun. Choose from a variety of Plan Bee brews, all of which are made entirely with locally sourced ingredients.
• Sip a glass of award-winning wine at Millbrook Vineyards and Winery as you enjoy the jazz stylings of the Daniel Bennett Group in the vineyard on Aug. 31. Eastern Dutchess County features gorgeous landscapes and natural vistas. Bring your blankets and lawn chairs and enjoy a picnic with dishes from local food trucks.
• 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. The garden is open Wednesday through Sunday from 10 a.m.–5 p.m., and it will also be open for Labor Day on Monday, Sept. 2. Docent-led tours are held Friday mornings at 10:30. Bring a picnic breakfast or lunch and spend the whole day. Wander among Innisfree's beautiful flowers and plants, breathtaking rock formations and all sorts of wildlife.
• Dutchess County features about 350 miles of scenic hiking trails perfect for beginners, experts and everyone in between. Check out our guide to the Top 10 Hidden Gem Hikes in Dutchess and plan a one-of-a-kind outdoor adventure!
• Who could turn down a summer barbecue? Join the celebration at Troutbeck for a delicious communal meal served buffet-style in a breathtaking setting. Chef Vinny will be cooking a whole pig on the fire truck, along with beef and chicken dishes and plenty of vegetarian options to satisfy any appetite. 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.
• Looking to sample some of Dutchess County's world-class cuisine this holiday weekend? Dutchess Tourism's CIA Chef Finder is a digital passport that helps you find Culinary Institute of America chefs who create world-class cuisine here in the heart of New York’s Hudson Valley.
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• Explore the remnants of a Scottish-style castle on Pollepel Island in the Hudson River! Climb aboard the Estuary Steward tour boat in Beacon and enjoy a scenic 30-minute ride to Bannerman Castle, where you'll embark on a guided tour of the castle ruins, the gardens, and the Bannerman Family residence. Tours will be offered Friday, Saturday, Sunday and Monday over the Labor Day holiday.
• Mount Gulian Historic Site in Beacon will be hosting its exclusive White Glove Tours every Sunday in September. Along with a tour of the house and grounds, visitors will be allowed to hold and examine artifacts representing 300 years of Mount Gulian's history, which spans from the time Indigenous people inhabited the banks of the Hudson River, through the Colonial Era, the American Revolution, and the Civil War. Inspect items from the museum collection, including precious family letters; documents and artifacts from the 18th and 19th centuries; English and Dutch family bibles; women’s and men’s Victorian Era clothing; military artifacts and more!
• Staatsburgh State Historic Site in Staatsburg is hosting two different themed tours over Labor Day Weekend. On Friday, take the Guided Landscape Walk of Staatsburgh's Grounds and explore how the property surrounding the Mills Family's lavish Gilded Age mansion was designed to reflect the family's luxurious lifestyle while deliberately hiding the turn-of-the-century technology and labor that made the estate run. On Saturday, join site staff for a one-hour conversation discussing the Gilded Age Black Community of Staatsburg. Examine census records, historic maps, and the larger context of race relations during the Gilded Age. Long marginalized in the historical narrative, the free Black community of the Village of Staatsburg reveals the triumphs and struggles of generations of African Americans in the Hudson Valley.
• As featured on the HGTV show "Flea Market Flip," you can find anything and everything at the Stormville Airport Flea Market, with hundreds of vendors offering antiques, jewelry, furniture, artwork, collectibles, crafts, new and vintage clothes and so much more.The market will be open Saturday and Sunday over the holiday weekend.
• If you enjoy shopping for antiques, then Dutchess County is the place for you. In fact, National Geographic included "Antiquing in the Hudson Valley" as one of the 20 top travel experiences for 2024 — on a list that includes safaris in Kenya, the Olympics in Paris, hiking up a volcano in Panama, and diving with sharks in Australia! Click here and see! Be sure to check out our Guide to Antiquing in Dutchess to find the best destinations for vintage shopping.
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• The Hudson River Sloop Clearwater, also known as "America's Environmental Flagship," will be embarking on a Public Sail Adventure on Monday, Sept. 2, leaving out of Beacon. Help hoist the mainsail and settle in for a fun Hudson River adventure! Be sure to visit our crew at the fish tank to see some Hudson River critters. Meet the Captain at the helm and take a turn on the tiller, and enjoy a traditional moment of silence broken by song before returning to the dock. The Clearwater was the brainchild of folk singer, environmental activist and Hudson Valley resident Pete Seeger, who announced in 1966 that he would “build a boat to save the river” along with his wife, Toshi, and a dedicated group of fellow musicians and activists. At the time, the Hudson was being choked by decades' worth of industrial dumping. The Clearwater, which is a replica of the Dutch cargo vessels that sailed up and down the Hudson River in the 18th and 19th centuries, was launched in 1969 and has been instrumental in advocating for environmental reforms that have brought the Hudson back to life.
• Sailing on the Hudson River offers spectacular views and unlimited photo opportunities of the surrounding highlands and native wildlife, along with, of course, the many iconic riverfront attractions, like Vanderbilt Mansion and the Walkway Over the Hudson, to name a couple. Charter a boat or book a cruise with Nothing But Time Sailing Charters in Poughkeepsie or the Tivoli Sailing Company and enjoy an unforgettable day on the water.
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• Labor Day Weekend is a perfect opportunity to see the Wassaic Project's summer exhibition, "Tall Shadows in Short Order," before it closes on Sept. 14. Maxon Mills, the Wassaic Project's gallery, is an historic, seven-story wooden grain elevator that has been repurposed into a uniquely magnificent exhibition space. The gallery is open Saturdays and Sundays from 12–5 p.m. or by appointment.
• Also closing soon is Dan Flavin's exhibition at Dia Beacon. Flavin's artwork was composed almost entirely of fluorescent lights of various colors arranged in various configurations. This exhibition will close on Sept. 23. Dia Beacon is an extraordinary collection of artwork from the 1960s to the present. Housed in a former Nabisco box-printing factory, it is one of the jewels of Beacon's vibrant arts scene. Among the artwork on long-term view at Dia Beacon is "Shadows" by Andy Warhol, which is a single painting composed of 102 separate canvases.
• Artists of all sorts, including painters, sculptors, photographers, ceramic artists, textile artists and mixed media artists, will open their studio doors to the public over Labor Day Weekend during the annual Art Views Studio Tour in Northern Dutchess. Enjoy a free, self-guided, tour as the artists share their creative environments and help visitors understand their inspirations and their techniques. The event is scheduled for Aug. 31 and Sept. 1, but many studios may also be open on Labor Day, Sept. 2.
• Start your holiday weekend early with a visit to the Frances Lehman Loeb Art Center at Vassar College in Poughkeepsie on Thursday evening. The Loeb stays open late on Thursdays (until 7 p.m. June through August and until 9 p.m. September through May). Among the 22,000 works of art in the Loeb's permanent collection are paintings by the leading artists of the Hudson River School movement of the mid-1800s, including Thomas Cole and Sanford Robinson Gifford, as well as masterpieces of the 20th century by Georgia O’Keeffe, Henri Matisse, Pablo Picasso and Jackson Pollock.
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