Chestertown is a tiny historical jewel nestled deep inside the Eastern shore of Maryland. Less than a two hour drive from Philadelphia, Baltimore, or Washington, D.C., it is well worth an afternoon or an overnight visit. Getting there is easily accomplished once you are clear of metropolitan traffic and quite relaxing as you pass massive crop fields, quaint villages, and rolling landscapes.

The city of Chestertown is chocked full of American history beginning over 300 years ago in what was the second largest shipping port for Colonial America via the Chester River (second to Annapolis). Today, brick streets, stately mansions, and decorative ironwork continue to represent the charm of a simpler time.

The waterfront is quiet and recently renovated into a park like setting with shade and walking trails. Strolling along the tree lined streets will provide glimpses of centuries gone by via the colonial homes that are in some cases, perfectly restored.

One such fabulous structure is the White Swan Tavern. Today it is a wonderfully restored building serving as a bed and breakfast. Proprietor Ian provided a fabulous tour of the building and grounds and was very happy to share fascinating accounts of historic antics that transpired on the property. It is a pre-revolutionary War structure that served as a backdrop during the formation of the country.

This is from their website:

“Joseph Nicholson purchased the property from Lovegrove in 1733, and built his home on the location which comprises the front portion of the present structure. As a member of the Committee of Correspondence, Nicholson had a very real role in the revolution and emergence of the young Republic.”

An American Flag with 35 Stars ~ c. 1863

In the center of town is a quaint and quiet block sized park offering tribute to all of the Chestertown-ians who fought and died in each of the countries wars; the American Revolution, both World Wars, Vietnam, and the Gulf wars.

Not to be missed during an afternoon visit is a stop at Play It Again Sam, a coffee / wine shop. Seating options here are varied and comfortable with outside seating, a rear outdoor patio filled with local art, and comfy chairs and couches inside. Wine is for sale by bottle or glass. If you choose the bottle, they can open it and provide glasses as you sit at a bistro table on the sidewalk and enjoy the opportunity to relax and/or people watch.

Finally, the town is home to liberal arts Washington College and worth at least a drive around to appreciate the magnificent colonial structures and expansive lawns.

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