3 days in Poughkeepsie Itinerary

3 days in Poughkeepsie Itinerary

Created using Inspirock Poughkeepsie sightseeing planner

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Route & dates

3 days in Poughkeepsie Itinerary

Start: Annapolis
Drive:  5​h 15​min
— 2 nights
Drive:  5​h 15​min
End: Annapolis


Poughkeepsie ©
Poughkeepsie, officially the City of Poughkeepsie, is a city in the state of New York, United States, which is the county seat of Dutchess County. Get out of town with these interesting Poughkeepsie side-trips: Norman Rockwell Museum (in Stockbridge) and Woodbury Common Premium Outlets (in Central Valley). Next up on the itinerary: take in the views from Walkway Over the Hudson State Historic Park, relax in the rural setting at Sprout Creek Farm, don't miss a visit to Art Centro, and explore the world behind art at Frances Lehman Loeb Art Center at Vassar College.

To see traveler tips, photos, reviews, and other tourist information, use the Poughkeepsie tour builder .

Annapolis to Poughkeepsie is an approximately 5.5-hour car ride. You can also do a combination of bus and train; or do a combination of flight and train. Traveling from Annapolis in October, Poughkeepsie is little chillier at night with lows of 43°F. Cap off your sightseeing on the 20th (Sun) early enough to go by car back home.

Things to do in Poughkeepsie

Museums Shopping Historic Sites

Side Trips

Franklin D. Roosevelt Presidential Library and Museum, Norman Rockwell Museum, Woodbury Common Premium Outlets
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