June is a wonderful time to visit New York’s Hudson Valley, and whether you’re planning a day trip, a weekend getaway or a longer excursion, there is so much to see and do here in Dutchess County.
Relax and recharge as you bask in the natural beauty and splendor of the Hudson River and surrounding mountains. Witness the past come to life at our many historic sites, including Gilded Age mansions and colonial-era homesteads. Let your creative spirit soar at our plenitude of performance venues and art galleries. Indulge in a diverse array of culinary flavors from all over the globe at our world-class restaurants.
There really is something for everyone here in Dutchess County, where there is an adventure waiting around every corner.
Here is a list of the Top 10 Dutchess Events in June of 2026 — a mere fraction of the county’s many can’t-miss attractions and experiences. Have fun — and be sure to keep that camera handy! Feel free to share your photos here, and tag @DestinationDutchess on social media.
Saturday, June 6, 2026, 3–7 p.m., on Main Street, Beacon
Celebrate all the best of what Beacon's vibrant and trendy Main Street has to offer at this fifth-annual event. Sample delicious foods and refreshing beverages from many of Beacon's finest restaurants and tap rooms. Check out the unique offerings from some of Beacon's most popular boutiques and businesses. Tickets are selling quickly and last year's event was sold out, so don't wait! Click here to purchase your tickets. Have your tickets ready and check in at one of three checkpoints to receive a wristband and a map: the Beacon Chamber of Commerce (1146 Wolcott Avenue) from 2–4:30 p.m.; Happy Valley Arcade Bar (296 Main Street) from 2–7 p.m.; or Liquid Fables (1 East Main Street) from 2–4:30 p.m. Main Street is within walking distance of the Beacon train station on the Metro-North Hudson Line, so getting there is a breeze!
Related: Celebrate Pride Month in Dutchess County with a host of fun events, including the Poughkeepsie Pride Parade and Festival on June 13. Click here for a guide to all the Pride celebrations in Dutchess.
Saturday and Sunday, June 6 and 7, 2026, 10 a.m., at the Dutchess County Fairgrounds, Rhinebeck
Find original fashions, accessories, jewelry and art at this thoughtfully curated market, which features contemporary fine crafts and artwork from more than 200 American makers. Enjoy gourmet foods, specialties, concessions and tastings from local distilleries and wineries, as well as family-friendly activities and craft demonstrations. Click here to purchase tickets.
Friday, Saturday and Sunday, June 12–14, 2026, at multiple Beacon locations
Calling all wordsmiths! Beacon’s sixth-annual literary festival will be a three-day collaboration of talented and renowned storytellers. Enjoy readings, performances, workshops, and much more. Come face-to-face with award winning writers and hear some fresh, new literary voices. Wayne Koestenbaum, Julia Phillips, Dawn Lundy Martin, Alexander Chee, MJ Corey, and translator Daisy Rockwell (granddaughter of Norman Rockwell) are just a few of the multi-award-winning writers and poets participating this year. Click here to see the festival schedule and to purchase tickets.
Sunday, June 14, 2026, 12–5 p.m., at Pete and Toshi Seeger Riverfront Park, Beacon
The strawberries are ripe for the picking here in the Hudson Valley, and to celebrate, the Beacon Sloop Club is hosting its beloved annual Strawberry Festival. Grab your forks and come on over for a fun, family-friendly event on the shores of the majestic Hudson River. Enjoy all sorts of strawberry treats while you listen to live music performances and shop from local vendors. To learn more, click here. The Strawberry Festival raises money for the public sailing program on Beacon Sloop Club’s boat, the Woody Guthrie. Click here to book a sail on the Woody Guthrie.
Related: Great Estates Garden & Landscape Weekends: June 6–7 and Aug. 1–2, 2026
• RevCon 2025 Revolutionary War Reenactment and History Fair (Saturday, June 13, 2026, 10 a.m., at the Franklin D. Roosevelt Presidential Library and Museum, Hyde Park): Dutchess County continues its multi-year commemoration of America’s semiquincentennial with RevCon 2025, the third-annual Revolutionary War Reenactment and History Fair. Reenactors will be on hand for weapons demonstrations and tactics, exhibitions of military camp life and uniforms, and question-and-answer sessions about life in Revolutionary America. Programs will include Michael Gabriel's lecture, “The Canonization of Richard Montgomery;” and Sara Evenson's presentation, “From the Colonial Hearth to Your Kitchen.” Click here for details.
• Revolutionary Cider Celebration (Saturday, June 27, 2026, 11 a.m., at Fishkill Farms, Hopewell Junction): Celebrate the start of summer in the orchards at Fishkill Farms, makers of Treasury Cider. It will be a day filled with Revolutionary War and Colonial-era history. Jonathan Kruk, the Hudson Valley's master storyteller, will regale families with Tales of Revolutionary Dutchess County. There will be hayrides, farm experiences, and, of course, apple cider! Click here to learn more.
Related: Story Finder Rev250 Discovery Trail
Saturdays and Sundays, June 20–Oct. 18, 2026, 2 p.m., at the Old Rhinebeck Aerodrome, Red Hook
Up, up and away! The Aerodrome is set to begin a new season of high-flying action with antique air shows every Saturday and Sunday! 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 vintage aircraft for each show. Open-cockpit biplane rides — which offer stunning views of the Hudson River and the surrounding highlands — are available before and after the air shows from 10 a.m. until twilight. Gates open at 10 a.m., which gives you plenty of time to check out the Aerodrome’s museum and grab a bite to eat at the snack stand. To purchase tickets, or to book your own biplane ride, click here.
Saturday, June 20, 2026, 7:30 p.m., at the Marriott Pavilion at The Culinary Institute of America, Hyde Park
The Northern Dutchess Symphony Orchestra explores the explosion of styles in American music from the 1950s through the 1970s with this special performance at The Culinary Institute of America. Enjoy music from the Beatles, Elvis, Burt Bacharach, Simon and Garfunkel, Herb Alpert, Brazilian Jazz, and more! The featured soloist is tribute artist Gene DiNapoli as Elvis. Click here to purchase tickets.
• Powerhouse Theater (late June through July, 2026, at multiple locations at Vassar College, Poughkeepsie): Powerhouse Theater at Vassar College has been an invaluable resource for emerging artists and their groundbreaking works for nearly 40 years. In fact, the 2016 Tony Award winners for Best Play and Best Musical — Stephen Karam’s "The Humans" and Lin Manuel Miranda’s "Hamilton," — both trace their roots to Powerhouse. This upcoming summer season is sure to feature another superb lineup of imaginative and insightful plays, workshops and works-in-progress. Perhaps one of this year's productions will be the next big smash! Check back for updates. To see the season schedule when it becomes available and to purchase tickets, click here.
• SummerScape and Spiegeltent (June 25–Aug. 16, 2026, at the Fisher Center, Bard College, Annandale-on-Hudson): Get ready for two action-packed months of performing arts at Bard’s annual SummerScape! There are many highlights on this year’s festival schedule. Enjoy performances of “Suddenly Last Summer,” a thrilling new opera based on Tennessee Williams’ play by the same name; and of Richard Strauss' opera "The Egyptian Helen." Lucinda Childs, a defining force in American dance, returns to SummerScape with a program of new and iconic works. The Spiegeltent, meanwhile, keeps the party hopping all summer long with live music performances, drinks and dancing. In the Spiegeltent, catch performances in the “Bluegrass on Hudson” series, as well as shows by Justin Vivian Bond ("music to lose your gay virginity by"), drag storyteller BenDeLaCreme, comedian and writer Jacqueline Novak, Hudson Valley-based singer-songwriter Al Olender, comedian Chanel Ali, and Spiegeltent favorite Martha Redbone, among many others. Click here to see the full lineup of SummerScape and Spiegeltent events and to purchase tickets.
Related: The Destination Dutchess Inspiration Finder Arts & Culture Trail is a free mobile passport program offering discounts at some of the best cultural institutions, exhibition spaces and performance venues in the county.
Thursday through Monday, June 25–29, 2026, at multiple locations
Upstate Art Weekend, which celebrates art and culture in the Hudson Valley and Catskills, is back for its seventh season and is five days long! Participating art organizations, galleries, museums, residencies and studios open their doors to the public, as this self-guided event welcomes tourists and locals alike to celebrate the cultural vibrancy of Upstate New York. Click here to see a list of participants, including several here in Dutchess County.
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Friday and Saturday, June 26 and 27, 2026, at the Orvis Sandanona Shooting Grounds, Millbrook
A team of internationally esteemed guest instructors will lead this two-day clinic, which offers an opportunity for skilled shooters to refine their technique. Participants will have access to these experts' tips, tricks, and adjustments that will enhance their success both on the clays course and in the field. Also included are five gourmet meals and unlimited clay target shooting. Click here to register.
