Thousands upon thousands of people visit Dutchess County each year, and they come here for all different reasons. Its wondrous natural beauty, its world-class cuisine and craft beverages, its vibrant arts and culture scene — these are only a few of Dutchess County's biggest attractions.
Not to be overlooked, however, are Dutchess County's many historical sites. Significant events have transpired here in Dutchess, and iconic people have called it home.
With several exciting events planned for the weekend of June 14–15, I Love N.Y. makes it possible to step back in time along its Path Through History and explore Dutchess County's rich heritage. Here's a look at what’s on the calendar:
Saturday, June 14, 11 a.m., at Staatsburgh State Historic Site, Staatsburg
Providing a delightful experience of bygone times, Dawn Elliott’s historic toys and games have been a highlight of events at many historic sites and museums. All are invited to experience a variety of lawn games and board games, or simply play with vintage toys. Stewart’s ice cream and a craft activity are included! Click here to complete the required registration.
Saturday, June 14, 10 a.m.–4 p.m. at the Franklin D. Roosevelt Presidential Library and Museum, Hyde Park
Dutchess County's multi-year commemoration of America’s semiquincentennial continues with RevCon 2025, the second-annual Revolutionary War Reenactment and History Fair. Last year's inaugural event was a tremendous success, and this year's festival is sure to be memorable! 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. A presentation by historian and author Todd Braisted, titled "They Absolutely Did Not Murmur: The Hudson Valley Takes Up Arms for King George," will examine the region's role in supporting the British war effort. Click here to learn more about upcoming Rev250 events as America's 250th birthday approaches on July 4, 2026.
Saturday, June 14, 11:30 a.m.–3 p.m., at the Hyde Park Railroad Station and Museum
The Hudson Valley Railroad Society hosts this annual event, which commemorates the time in 1939 when President Franklin D. Roosevelt hosted England's King George VI and Queen Mary for a picnic at his hilltop retreat, Top Cottage. The king and queen left from the Hyde Park Station after the picnic. The New York Times headline read: "King Tries Hot Dog and Asks for More." Enjoy museum tours and history discussions along with some tasty hot dogs! Click here to register.
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Saturday and Sunday, June 14 and 15, 9 a.m.–6 p.m. at the Franklin D. Roosevelt Presidential Library and Museum, Hyde Park
When President Franklin D. Roosevelt proposed the idea of building a library to house his papers and memorabilia, detractors believed he was simply interested in constructing a monument to himself. Roosevelt, however, viewed the library as a solution to two problems: how to simultaneously preserve and provide public access to the records of his presidency. His was an attitude of “open government,” believing that the people of the United States were entitled to a better look at how their government was working. As an avid amateur historian, Roosevelt recognized the value of his papers and believed they should be saved for future historians and the American people. FDR created America's first Presidential Library, and all are welcome to stop by and see his vast collection of papers, letters, gifts, memorabilia and more. Click here to learn more.
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Saturday and Sunday, June 14 and 15, 10 a.m.–3 p.m., at Locust Grove Estate, Poughkeepsie
Enjoy a kid-friendly day in the gardens at the Italianate mansion and summer home of telegraph inventor Samuel F.B. Morse. Join the Enchanted Gardens self-guided scavenger hunt for whimsical and adorable fairy houses and gnome houses hidden among the flowers and trees. Each house celebrates a different heirloom flower or historic tree that grows on the estate. Wear your wings, crowns and hats, or buy some in the shop! Be sure to check out the beautiful historic trails leading down to the Hudson River's edge. Bring a picnic to enjoy under the trees. Click here to purchase tickets.
Related: The Destination Dutchess Tourism Story Finder History and Heritage Trail
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Saturday and Sunday, June 14 and 15, 10 a.m., at the Old Rhinebeck Aerodrome, Red Hook
The action is taking off at the Aerodrome, with air shows every Saturday and Sunday from June 14 through Oct. 19! Gates open at 10 a.m., with pre-show activity starting at 2 p.m. and the air show starting at 2:30. Open-cockpit biplane rides are available before and after the air shows from 10 a.m. until twilight. The Aerodrome's museum opens at 10 a.m. and the snack stand opens at noon. 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. Click here to learn more.
