4. Poughkeepsie
As opposed to many smaller towns on this list, most people on the East Coast have likely heard of Poughkeepsie or its city counterpart. Poughkeepsie is a college town, home to the beautiful campuses of Vassar and Marist. The town has a unique variety of things to do, from visiting the historic Locust Grove Estate to walking the world’s longest elevated pedestrian bridge, the Walkway, over the Hudson River.
If you get thirsty head to the Mill House Brewing Company, which serves high quality and classy pub food and local beer. Much like many restaurants in Poughkeepsie that have been converted from old factories, the Mill House Brewing Company used to be an actual running mill. Just under thirty minutes away from Poughkeepsie is a unique spot to spend the night in New Paltz called Mohonk Mountain House. Considered a Victorian castle resort, guests can step back in time while enjoying finer things like heated swimming pools and four-poster beds.