Chestertown Maryland Hotels

While not a large town, it attracts people because it lies within easy driving distance of Annapolis, Baltimore, Washington, and Philadelphia. Chestertown, founded in 1706 rose in stature when it was named one of the colony's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-18th century, Chestertown trailed only Annapolis as Maryland's leading port. That popularity has experienced a modern-day resurgence.

Boston may be known for it's Tea Party, but Chestertown also has one. Here is a quote from Wikipedia. "In May of 1774, five months after the British closing the port of Boston after the Boston Tea Party, the citizens of Chestertown wrote a set of resolves that prohibited the buying, selling, or drinking of tea. In an act of colonial defiance they held their own "tea party" on the Chester River in Chestertown. The Chestertown Tea Party Festival today commemorates the historic event with a re-enactment of the "tea party." Colonial re-enactors are thrown overboard with the tea by the crew of the Schooner Sultana. A parade down High Street to the Chester River follows with colonial music and dance, fife and drum performances, puppet shows, colonial crafts demonstrations and sales, military drills, and a walking tour of the historic district. It is the town's biggest weekend of the year as tourists cram the streets strolling among booths filled with crafts and food."