Founded in 1706, Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown's Historic District to admire the fine colonial residences is a must! If you're a history buff, fond of cobblestone streets and gas-lit lanterns, you'll love living in Chestertown, Maryland. Founded in 1706, it was named one of Maryland's six "royal ports of entry" in the 18th century. Shortly after the Boston Tea Party, Chestertown citizens resolved to prohibit buying, selling, or drinking tea, and they were even said to have held their own tea party on the Chester River. Besides its active history, the town has many amenities and activities, and with its idyllic location and natural beauty, you're bound to love living in Chestertown.