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.
Chestertown, Maryland is a small town on the Eastern Shore, in Kent County, one of Maryland’s least populous counties. It sits on the Chester River, which winds inland from the Chesapeake Bay starting just north of Kent Island, and separates Kent and Queen Anne counties. (Kent Island is actually part of Queen Anne County.) Like most Eastern Shore rivers, the Chester is really just an extension of the Bay, placid and tidal.
Chestertown is reached by heading north on Rte. 301 at the 301-50 split in Queenstown. This distinguishes it from the rapidly developing communities along Rte 50, like Kent Island, Easton, and Cambridge, and from the mass of traffic that heads through these places to Ocean City, MD every summer weekend.
Kent County has a few other towns, most notably Rock Hall on the Bay, but is mostly rural. The county comprehensive plan is intended to maintain that, and emphasizes new development around existing population centers. This is in contrast to Queen Anne County, where developments appear to be springing up in cornfields everywhere.
Chestertown was once a major port of call on the Chesapeake. It has a large number of well-preserved or restored old homes and other buildings, along and close to the waterfront, and a downtown area with a number of eclectic shops and small restaurants.
First, an introduction. We are a middle-aged couple in our mid-50’s, with three children ranging in age from almost 20 to 26. I’ve been working as a NASA contractor in Greenbelt, MD for over 30 years. My wife has worked as an administrator for another government contractor for several years. We have lived in our current house in a nearby suburb for more than 20 years.
We did not start out with any specific plans to move. However, I think that we have always felt that at some time in our lives, we would live somewhere that has a waterfront. My wife and I have always been attracted to the water. Most of our vacation have been at beach areas, in such places as Rhode Island and the Outer Banks. This goes back to my wife’s childhood and her family’s vacations in Point Judith, RI. She and I went on several of those vacations, along with our children when they arrived. We discovered the OBX some years back.
We have enjoyed being near the Chesapeake Bay as long as we have lived in Maryland. We regularly visit Annapolis to wander down around the harbor. When our children were old enough to be left alone, we starting “running away” to explore Bay-front communities, mainly on the Western Shore.
We also enjoy being out on boats — on reasonably calm water, that is. I’ve never actually owned a boat (except for a canoe), but find the idea of sailing to be very appealing. We took a ride on the skipjack Rebecca T. Ruark out of Tilghman, MD about 10 years ago. Our good friends recently bought a lakefront house and have a ski boat on Lake Gaston in NC, and we have spent some delightful weekends there.