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 20–21, 2026, 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:
• Staatsburg Village Walking Tour (Saturday, June 20, 2026, 10 a.m., starting at St. Margaret's Epicopal Church, Staatsburg): Visit several historic locations, including long forgotten factories, bustling downtown hotels and medieval memorials in Northern Dutchess. Explores the village of Staatsburg's close relationship with the Mills family and their estate on a 90-minute guided walk. Discover Staatsburg's vibrant past and the lasting legacy of Ruth and Ogden Mills beyond their estate walls. At the turn of the century, this hamlet was a thriving hub of businesses and manufacturing, fueled by these landed estates and the modernizing nation. Though this event is free, reservations are required; to save your spot, book here.
• History Hidden in the Woods (Sunday, June 21, 2026, 10 a.m.): Did you know there are ruins within Mills-Norrie State Park? This gorgeous land served as the ideal setting for grand Hudson River-front estates, and it is yours to explore on this two-hour guided hike. The program details the transformation of these structures through the centuries, from Staatsburgh’s founding as a gentleman’s farm in the 1700s to the development of The Point and Stonehurst estates in the 19th century. Click here to reserve your place at this free event.
Related: Destination Dutchess Story Finder Rev250 Discovery Trail
• America 250: The Livingstons of Clermont in 1776 (Saturday, June 20, 2026, 3–4 p.m.): Join Interpretive Programs Assistant Emily Robinson for a talk about the Livingstons of Clermont in 1776 and the events that spurred them toward independence. Enjoy some liberty-tea punch and spice cake as you follow the international incidents and familial circumstances that eventually brought the British to the patriots' doorstep. This presentation compliments Clermont's presentation on June 14, 2026, “America 250: The People of Clermont in 1776,” presented by Site Manager Geoff Benton. Click here to register. Clermont Mansion was home to seven generations of the powerful and wealthy Livingston family. The original home was burned down in October of 1777 by British soldiers because of the family’s deep patriot ties, and Margaret Beekman Livingston worked hard to have the home rebuilt. Margaret's husband, Judge Robert R. Livingston, had been a member of the Stamp Act Congress. Her son, Henry Beekman Livingston, was colonel of the Fourth New York Regiment. Her oldest son, Chancellor Robert R. Livingston, was a member of the Continental Congress and helped draft the Declaration of Independence.
• Lindy Hop at Locust Grove (Saturday, June 20, 2026, 3–10 p.m.): Locust Grove and Got2Lindy Dance Studios present this fun event, which begins with an all-levels Lindy Workshop led by Linda and Chester Freeman of Got2Lindy. Don't know how to swing dance? Head to the beginner swing dance lesson at 7 p.m., after which Danny Lipsitz and the Brass Tacks will provide the tunes to keep the party hopping! Click here to purchase tickets.
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• Air Show: Living History (Saturday and Sunday, June 20 and 21, 2026, 10 a.m.): The action is taking off at the Aerodrome, with air shows every Saturday and Sunday from June 20 through Oct. 18, 2026! 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.
