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Discover Dutchess Sites on Path Through History Weekend (Oct. 11-13)

Date Published: August 13, 2025

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 October 11-13, 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, October 11, 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.

Staatsburgh State Historic Site, Staatsburg. A family walks along the grassy embankment in front of the 79 room stone mansion with its white columns and facade.
Staatsburgh State Historic Site, Staatsburg

History Hidden in the Woods

Sunday, October 12, 10 a.m., starting at Staatsburgh State Historic Site, Staatsburg

Did you know there are ruins witin 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: The Destination Dutchess Tourism Story Finder History and Heritage Trail


A working replica of Charles Lindberghs plane, the Spirit of St. Louis, at the Old Rhinebeck Aerodrome, Red Hook
A working replica of Charles Lindbergh's plane, the Spirit of St. Louis, at the Old Rhinebeck Aerodrome, Red Hook

Air Show: Living History

Saturday and Sunday, October 11 and 12, 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.

Market Day Craft Fair in Fishkill

Sunday, October 12, 10 a.m., at Van Wyck Homestead Museum, Fishkill

Experience a Revolutionary War-era market day this October. Come for the masterful crafts and stay for lunch, fresh apple fritters and a tour of the Van Wyck Homestead Museum. In the colonial era, market days allowed craftspeople, farmers, and friends to come together for fellowship and stock up on needed goods. Peruse works from over thirty vendors, including watercolor art, wooden gifts, pottery, jewelry, handmade soaps, knit clothing, and more. Plus, don tri-corn hats, mob-caps and other period-accurate garb sold at the museum gift shop. Lastly, Hamilton fans will adore the special exhibit celebrating the 200th anniversary of the the Marquis de Lafayette's tour of the United States. 

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