With so many fun, family-friendly events on the calendar, August is always an exciting time to visit Dutchess County. Located in the heart of New York’s picturesque Hudson River Valley, Dutchess is the perfect destination for a getaway any time of year, of course, and August has several signature annual attractions that make it especially memorable for adults and kids alike.
There are so many great things happening all over Dutchess County in August of 2026! Here is a list of 10 guaranteed-to-please excursions you should consider as you try to squeeze as much fun as possible into the final weeks of your summer vacation.
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Nothing symbolizes a relaxing summer in the country quite like a field of sunflowers, and August is prime sunflower season in the Hudson Valley. There are several upcoming sunflower-themed attractions in Dutchess County you won’t want to miss.
• Ninth-Annual Sunflower Cutting Season at Hudson Valley Cold Pressed Oils, Pleasant Valley (Every Thursday–Sunday, Aug. 6–Sept. 6, 2026): Cut your own beautiful sunflowers at this popular annual event, which features acres and acres of bountiful blooms. The expected opening date will be Friday, Aug. 6, and every Thursday, Friday, Saturday and Sunday while the fields are open, they will have local musicians performing from 4:30 p.m. until sunset. Dates and times are subject to change due to the weather and flower availability. To stay up to date on sunflower-cutting events, live music shows and other special events at the farm, click here. In the meantime, feel free to check out the HVCPO website and browse their online shop for many sunflower-based products, including gluten-free sunflower muffin mix, hummus made with sunflower oil and all sorts of sunflower-themed jewelry items and T-shirts.
• Eighth-Annual Sunflower Festival at Barton Orchards, Poughquag (Aug. 28–30 and Sept. 4–7, 2026): Enjoy a scenic hayride to a rolling five-acre field filled with thousands of sunflowers of various types. Cut your own sunflowers (bring your own shears if you have them) and enjoy live music, wine and beer served next to the field and a variety of craft vendors. The farm market features an assortment of signature jarred products, produce and local products. The Tap Room will be open with local beers and hard ciders on tap, as well as wine and spirits. The kids will love the fun park — with its giant slide — as well as the petting zoo. Well-behaved dogs are welcome on a leash, or off the leash in the dog park. Click here to purchase tickets. Can't make it to the orchard? Be sure to stop by the Apple Core year-round farmstand in Poughkeepsie for all your Barton Orchards favorites, like apple cider donuts, maple syrup and all sorts of sweet treats, as well as fresh produce, eggs, meat, dairy and unique jarred products. Special orders are always welcome. Call the farmstand at (845) 471-2879.
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Related: The Destination Dutchess Farm Finder Ag-Adventure Trail
Saturday, Aug. 1, 2026, 12–2 p.m., at College Hill Park, Poughkeepsie
There are many examples of people in Dutchess County who have heroically championed the fight for equality in America, from the Abolitionist Movement through the Civil Rights Movement. Celebrated activist, writer and orator Frederick Douglass — who had escaped bondage in Maryland and went on to become an iconic figure in the antislavery and women’s suffrage movements of the 19th century — delivered an inspirational speech at the Collegiate School in Poughkeepsie (now College Hill Park) on Aug. 2, 1858, and implored the audience of 4,000 to demand justice and end slavery in the United States. In commemoration of this important event, the City of Poughkeepsie and the nonprofit organization Celebrating the African Spirit have joined forces to present the annual Frederick Douglass Day on the site of his impassioned speech. Music, food and performances will honor the significance of Douglass' speech and applaud the local people who were in attendance and witnessed history that day. To learn more about the history of College Hill Park and ongoing efforts to preserve it, click here.
• Jazz in the Vineyard with Yankees Legend Bernie Williams (Saturday, Aug. 1, 2026, at Millbrook Vineyards and Winery, Millbrook) — Millbrook Winery hosts its annual jazz concert featuring former New York Yankees center fielder and jazz music icon Bernie Williams and his Band of Friends. As part of the festivities, a fifth vintage of Bernie’s Blend red wine will debut the evening of the concert. Click here to learn more.
• Jazz in the Valley (Sunday, Aug. 16, 2026, 12 p.m., at Waryas Park, Poughkeepsie) — This annual festival on the Poughkeepsie waterfront is a celebration of jazz the whole family will love. This year's concert features an exciting mix of young and veteran musicians, including Lisa Fischer, Sharp Radway, Chief Baba Neil Clarke, Alex Blake, Zaccai Curtis, Javon Jackson, and Luques Curtis. General seating is available under the tent, or you can bring your own chair or blanket and relax on the lawn. Waryas Park is within walking distance of the Poughkeepsie train station, which serves both Metro-North and Amtrak trains. Click here to purchase tickets.
Saturday and Sunday, Aug. 1–2, 2026, at multiple locations
Explore the gardens and landscapes of Dutchess County’s Great Estates and experience the outdoor beauty of homes from the Revolutionary War, the Gilded Age, and the World War II eras. Locations hosting events the first weekend in August include Blithewood Garden on the Bard College campus in Annandale-on-Hudson, Wilderstein Historic Site in Rhinebeck, Staatsburgh State Historic Site in Staatsburg, Mount Gulian Historic Site in Beacon, the Beatrix Farrand Garden at Bellefield on the grounds of the Home of Franklin D. Roosevelt National Historic Site in Hyde Park, and Clermont State Historic Site in Germantown. Click here for details.
Sunday, Aug. 2, 2026, 12–7 p.m. at Waryas Park, Poughkeepsie
Come and be a part of a colorful celebration of Mexican culture on the shores of the Hudson River. La Guelaguetza brings everyone together for an afternoon of fun which includes traditional Oaxacan dances and costumes, live music, artwork and crafts, kids' activities and, of course, a lot of authentic Oaxacan food! Oaxaca is a state in southern Mexico whose customs and cuisine date back hundreds of years to its indigenous inhabitants. Click here for updates.
Aug. 7–9 and Aug. 13–16, 2026, at The Fisher Center at Bard College, Annandale-on-Hudson
The 36th Bard Music Festival will explore the life and work of Wolfgang Amadé Mozart, one of the most celebrated and recognized names in classical music. The festival, split over two weekends in August, features a robust schedule of programs and panel discussions. To see the complete schedule and to purchase tickets, click here. Chartered coach transportation from New York City is available for select SummerScape and Music Festival programs; click here for details.
Sunday, Aug. 16, 2026, 12–5 p.m., at Pete and Toshi Seeger Riverfront Park, Beacon
Featuring fresh-picked, sweet Hudson Valley corn, the Beacon Sloop Club’s annual Corn Festival is a fun, family-friendly event on the banks of the beautiful Hudson River. Admission is free and all are welcome! Enjoy treats such as chilled watermelon, freshly squeezed lemonade and, of course, lots of delicious corn, boiled to perfection and served with butter and special toppings. Two solar-powered stages will provide live music throughout the day. Numerous food and craft vendors will be on hand. Environmental non-profits will feature displays of local river history and the environment along with information about their organizations. There will be plenty of free activities for children. Click here for more information about the club. Free sails aboard the Beacon Sloop Club’s boat, the sloop “Woody Guthrie,” are open to the public on weekday evenings. To make reservations, call (845) 527-8671.
Related: Check out all these Farmers Markets in Dutchess County!
Sunday, Aug. 23, 2026, 12–6 p.m., in the Academy Street Historic District, Poughkeepsie
Stroll through Poughkeepsie’s Southside Historic District and enjoy this free, family-friendly live music event that is always a big hit! Walk along Academy, Garfield, Barclay and Montgomery streets to hear local musicians perform right on the front porches of the neighborhood’s beautiful homes. Bring a lawn chair and sit and enjoy. Grab a bite to eat from a variety of local food vendors. For updates, click here.
Aug. 25–30, 2026, at the Dutchess County Fairgrounds, Rhinebeck
Here is a can’t-miss experience that should be on every Hudson Valley itinerary and bucket list. The Dutchess County Fair has been a highlight of the summer season for generations. This year's 180th fair features another action-packed lineup of carnival rides, concerts, livestock shows and competitive, historical and educational exhibits, along with an endless supply of tasty food and beverages! Grandstand performers in 2026 will include Chase Matthew (Aug. 25), .38 Special (Aug. 26), Journey from the Heart (Aug. 27), Almost Queen (Aug. 28), Tyler Braden (Aug. 29) and the Painted Pony Championship Rodeo (Aug. 30). Click here to learn more.
Related: Aug. 27, 2026, is ThinkDIFFERENTLY Thursday at the Dutchess County Fair. To learn about all the inclusive and accessible features of the fair, click here.
Aug. 29–Sept. 12, 2026 at Kaatsbaan Cultural Park, Tivoli
The 2026 Annual Festival will run on three consecutive weekends and includes thoughtful offerings and original performances by artists innovating in dance, music, theatre, storytelling, and more. The 2026 Annual Festival marks the return of Kaatsbaan’s outdoor Mountain Stage with its expansive views of the Catskill Mountains. Throughout the festival, the 2026 Visual Arts Exhibition, "Earthly Delights," will be available to view. The Performance Lending Library features a curated selection of audio-guided physical experiences adapted for Kaatsbaan’s scenic 153-acre campus, each less than 30 minutes. Click here to see the full schedule of festival events.
Saturday and Sunday, Aug. 1 and 2, 2026, 10 a.m., at the MJN Convention Center, Poughkeepsie
More than 100 exhibitors will be on hand at the family-friendly two-day festival, which will also feature cosplay contests, gaming, panel discussions and more! Click here for information on ticket packages, including the VIP package, which includes all sorts of exclusive perks and giveaways. If time allows, make a weekend out of it! The recently refurbished DoubleTree by Hilton Poughkeepsie is only steps away from the MJN Center and is within walking distance of a variety of fantastic restaurants.
