Chestertown is also home to Washington College, a small liberal-arts college that boasts of being one of the oldest colleges in the country. According to their web site: “Founded in 1782 under the patronage of George Washington, Washington College was the first college chartered in the new nation.”
The college is, in fact, the reason that we found Chestertown to begin with. Our second daughter applied and was accepted there, and we visited the campus in Spring 2005. Although she did not attend the college, I did get a good look at the town that day. Even then I observed that it was charming, in a sort of Hollywood-movie-ideal-small-town kind of way. Before then we had never spent any time on the upper Eastern Shore, except to take Rte. 301 as an alternative to 95 on our way to or from New Jersey.
I brought my wife out to see Chestertown sometime later that year. We actually did not spend a lot of time in the town that day, as we were also heading farther north to see Crystal Beach and Chesapeake City, other upper Chesapeake Bay places I had read about. We returned in early December, to participate in a holiday historic house tour. We also had dinner for the first time at the Blue Heron, a small but very epicurean restaurant and still our favorite place to dine in town.
I could go on about the appeals of Chestertown and Kent County, but I think the point is made — we were smitten.