Chestertown was established as New Town in 1706, one of six sites then designated as colonial ports of entry and the seat of the Eastern Shore’s first county. Significant growth began after 1730 when the town grid was laid out. Renamed Chestertown in 1780, the port enjoyed a heyday between 1750 and 1790 as the Eastern Shore’s primary shipping location for tobacco and wheat. Wealthy citizens erected the fine houses that established Chestertown’s reputation as second only to Annapolis in architectural splendor. Most were built along Water Street, allowing their merchant owners a view of the wharfs and warehouses located at the terminus of High Street, the main commercial thoroughfare. These include Widehall (1769–1770; 1909 restored; 101 N. Water), Denton House (1784–1787; 1970 restored; 107 N. Water), the William Murray House (1743, 1771; 106 N. Water) and the Custom House (ES19).
As the county’s governmental and commercial center, Chestertown became the focus for arts and culture, including the establishment in 1782 of Washington College (see ES22). Prominent for its location on the primary route between Philadelphia and Virginia, Chestertown offered inns and taverns, only a few of which survive, such as the White Swan Tavern (c. 1760; 231 High Street). By 1800 Chestertown was over-shadowed by the port of Baltimore, yet it remained vital to the development of Maryland’s Upper Eastern Shore. A building boom began in the post-Civil War era beginning with the construction of the new Italianate Kent County Courthouse (c. 1865, John A. Kennard; 103 N. Cross Street) and Court Row (c. 1850–1890; 109–117 Court), a customary row of one-story, private lawyers’ offices. Growth was fueled by the arrival of the Kent County Railroad in 1872. Combined with steamboat traffic, the railroad facilitated the transport of agricultural goods as well as a canning industry. The current overlay of late-nineteenth-century buildings speaks to that era, represented by such buildings as the Second Empire Stam Hall (1886; 220 High Street), the largest and most elaborate commercial building in Chestertown. It was built for merchant and druggist Colin F. Stam to combine retail and public meeting space. Stam’s own house (1877, H. M. Stuart; 114 Washington Avenue) was the first in a number of highly ornate, upper-middle-class houses built along Washington Avenue. The old town area was designated a National Historic Landmark District in 1970.
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