Thousands upon thousands of people visit Dutchess County each year, and they come here to the heart of the Hudson Valley 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 Oct. 10–12, 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:
• The REAL Gilded Age: America’s Elite in the Downton Abbey Era (Saturday, Oct. 10, 2026, 10 a.m.): This tour of the Mills family's opulent Gilded Age mansion highlights the real-life characters and themes at Staatsburgh that parallel Downton Abbey and HBO’s The Gilded Age. Led by a costumed interpreter, the tour shows how the Mills family and their servants conducted a busy weekend of high society entertaining, comparing Staatsburgh to what viewers saw on TV. Click here to purchase tickets.
• Gilded Age Scandals! (Sunday, Oct. 11, 2026,11 a.m.): Ruth and Ogden Mills were paragons of respectability, but some of their Gilded Age peers were not! Learn about the scandalous behavior and intrigues of America's elite at the turn-of-the-century while touring the Mills family mansion with a costumed guide. This tour, which is not recommended for kids, will include visiting additional parts of the mansion not on standard tours, including the partially restored historic kitchen. Purchase your tickets here.
• Staatsburg Village Walking Tour (Sunday, Oct. 11, 2026, 2 p.m., starting at St. Margaret's Epicopal Church, Staatsburg): Explore the village of Staatsburg's close relationship with the Mills family and their estate on this two-hour guided walk. Visit several historic locations, including long forgotten factories, bustling downtown hotels and medieval memorials in Northern Dutchess. 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 estates and the modernizing nation. Tickets are required for this event; to save your spot, book here.
• A Life in Service (Sunday, Oct. 11, 2026, 2 p.m.): It took a small army to run a Gilded Age estate. See the 79-room Mills family mansion through the eyes of the domestic servants, who rose before dawn and toiled until after midnight to provide exemplary service in the mansion. The tour — led by a costumed guide — will include visiting the servants’ wing, a striking artifact of servant life and work that features the newly retiled and partially restored kitchen, along with other rooms for servant use. To purchase tickets, click here.
Related: Destination Dutchess Story Finder Rev250 Discovery Trail
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• Air Show: Living History (Saturday and Sunday, Oct. 10 and 11, 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, and a World War I tank, along with many antique automobiles. Click here to learn more.
• October Curator's Tour (Saturday, Oct. 10, 2026, 10:30 a.m.): Innisfree Garden landscape curator Kate Kerin leads this lively 90-minute tour exploring Innisfree, a powerful icon of mid-20th-century design now recognized as one of the world's 10 best gardens and listed at the highest level — exceptional national significance — on the National Register of Historic Places. In a story that reads like the Great American Novel, learn about the people and ideas that shaped this living landmark. Set within a natural bowl surrounding the 40-acre Tyrrel Lake, it was created over six decades through the vision of estate owners Walter and Marion Beck and landscape architect Lester Collins. Together, they developed a distinctly American garden inspired by Chinese and Japanese landscape traditions, where art and nature exist in careful balance. Click here to purchase tickets.
