Chestertown is small town of about 5,000 that is east of Baltimore on the Delmarva Peninsula, northeast of Annapolis on the Chester River. The population is growing as more people consider it a quiet alternative to places like St. Michaels. In the mid-eighteenth century Chestertown was considered Maryland's second leading port after Annapolis. Chestertown is home to Washington College, the 10th oldest college in the U.S. The College has a large campus as you enter town. Then the charming downtown is set around a square and the Courthouse. Beautiful brick and wood houses are close together along some very cute streets. Chestertown was named to the 2007 list of America's Dozen Distinctive Destinations by the National Trust for Historic Preservation. Photo of Chestertown from above courtesy of Wikipedia and Jennifer Schmidt in the public domain.