History in towns: Chestertown Maryland

Magazine Antiques, April, 2003 by Gloria Seaman Allen

On the eve of the American Revolution, Chestertown, a customs port and seat of Kent County on Maryland's Eastern Shore, retained much of its early charm and vitality. (1) When Philip Vickers Fithian (1747-1776) passed through Chestertown in 1774 he noted in his diary:

Rode from Rock Hall over a delightful part of the country to Chester-Town 13 Miles--this is a beautiful small Town on a River out of the Bay navigable for Ships. The Situation is low & I apprehend it is subject to summer Fevers--It has an elegant I may say grand Court-House, in which is the town Clock--Mr. Wall the Comedian, has been for several Evenings past exhibiting Lectures in Electricity, & I understand with some considerable applause. They have a lottery here on foot & to be drawn in May next for to assist them in building a market-House Town-Wharf &. (2)

In 1774 Chestertown was a small urban center that had become active in the West Indies wheat trade earlier in the eighteenth century. Local ships carried grain products to Ireland, Spain, and Portugal, and later to the wine islands of Madeira, Cape Verde, and the Azores, where grain was traded for wine or salt. (3) As an official port of entry for British goods and a stop on the ferry and stage lines between Annapolis and Philadelphia, Chestertown became by mid-century the largest and most important town on the Eastern Shore of Maryland, with a population of about thirteen hundred. (4) It was during this period, sometimes referred to as the "Golden Age," that affluent merchants and shipowners began to erect impressive brick buildings along the waterfront, a number of which still stand today (see Pl. IV).

Chestertown can trace its beginning to the early eighteenth century when the introduction of wheat cultivation in Kent County "spurred the growth of a market town on the Chester River." (5) The riverside became a logical location for a new town, as authorized by the 1706 Act for the Advancement of Trade and Erecting Ports and Towns in the Province of Maryland. (6) Designated one of Maryland's six official ports and the new county seat, the town was surveyed in 1706/1707 by Simon Wilmer II (1686-1737) on one hundred acres of his land grant, "Stepney,, (7) New Town, as it was known until about 1730, was laid out on a grid plan bounded by the Chester River and two minor streams (see Fig. 1). One hundred residential and commercial lots extended northwest from the river, while lots in the center of town were reserved for a courthouse, church, marketplace, and cemetery. The principal road, High Street, followed a natural ridge and ran from the river to the far boundary of the town. (8)

After an initial period of stagnation, the town began to grow. In 1730 the Maryland Assembly passed a measure to resurvey the one-hundred-acre site. An additional road, Front Street, was created parallel to the river with lots reserved for warehouses and other commercial buildings. Owners of unimproved lots, in order to maintain their tides, were given eighteen months in which to build houses of at least four hundred square feet. (9) As the population increased, land values rose dramatically and commerce and shipping expanded. (10)

The rapid transition of a rural county seat into an urban commercial center brought conflict. People who had formerly let their livestock roam freely could no longer do so after legislation passed in 1732:

That diverse Persons...do raise and keep large Quantities of Swine, Sheep, and Geese...whereby not only the Gross necessary for the Support of the Cows and Horses of the Inhabitants is consumed; but that also, the Ground is so rooted up, and the Streets so broke, that in Winter or wet Weather, they are almost impassable; also, that the Swine there are so numerous and ravenous that they break into Warehouses where grain is stored, and that several young Children have been in Danger of being devoured by them; and that the Inhabitants cannot preserve their Gardens and Inclusures from being broke down and destroyed by them. (11)

One of the many artisans attracted by the commerce of the town was John Lovegrove, who established his tannery and shoemaking business on High Street as early as 1720. His two-room frame dwelling was located on the property acquired in 1733 by Joseph Nicholson. Nicholson's five-bay building, with its glazed header Flemish bond brick facade had a gambrel roof typical of local vernacular architecture (see Pl. III). (12)

Nicholson distinguished himself as the town sheriff, register of wills, and as a colonel in the American Revolution. The property was sold in 1793 to John Bordley, who further enlarged the house during his eight-year ownership. (13) Nicholson or Bordley may have run a tavern here, but documentary evidence for such use only comes from the estate inventory of the next owner, Isaac Cannell (d. c. 1821), which listed "a billiard table leased with the Tavern" as well as nineteen bedsteads, twenty three tables, thirty-six chairs, and an ample supply of bed linens, china, and earthenware. (14) Now known as the White Swan Tavern, the building was restored in 1978 to the 1793-1853 period of its history as a working inn. (15)