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Birds eye view of Chestertown

Library of Congress, Geography and Map Division

Chestertown (pop. 2000 4,746), seat of Maryland's second oldest county, is situated midway up the Chester River (actually an estuary) and was established as town in 1706. Enclosed by the Sassafras River to the north and the Chester to the south, the largely agrarian county of Kent has depended on this town for its many services and amenities for close to three centuries. It took some time before the site of the town was selected, but the records seem to show that the building of a court house near its present location helped bring about its designation as a royal Port of Entry for the upper Eastern Shore of the colony.

Early Economy and Population
The combination of commerce--tobacco crops in the early eighteenth century and wheat starting by the time of the American Revolution--along with its legal importance, led to a steady climb in its population. In 1750, there were about 100 inhabitants in the town. Several planter-merchants were shipping large quantities of wheat to southern Europe on their own vessels by this time. The first census of the new Republic in 1790 revealed a population for the county of 6,748 whites, 655 free blacks, and 5,433 s1aves. Because the censuses were conducted county-wide well into the nineteenth century, lacking other clear evidence, it is almost impossible to determine the actual numbers of town residents during the decades before the Civil War. In 1790, only 12 heads of household were specifically identified as residents of Chester Town (in order to avoid confusion with others with the same family name).

There was a general county decline, owing to the rise of Baltimore and Philadelphia as centers for trade. The development of railroads, as the American population spread westward, meant that the total county population also dropped from 12,836 in 1790 to 11,386 in 1850. Studies have shown that the center of the entire United States population was actually just a few miles outside Chestertown in 1790, whereas by 1850 it lay near Parkersburg, West Virginia.

Planning the Town
In 1730, an orderly town plan was devised for the farmland acquired from the large landowner Simon Wilmer.  It consisted of 100 one-acre lots and soon some of the large number of brick mansions, smaller homes, and public buildings for which the town is famous were being built. During the latter eighteenth century, only Annapolis surpassed Chestertown in the number of significant structures that, for the most part, still survive today.  Buildings lined an unusually wide main street called High, and along Front Street at the river, as well as in the general area of the courthouse. The grid-like plan provided for an ample public space, which near the town center contained the Anglican Emmanuel Church, its cemetery, a jail, a market house, and, in 1801, a Methodist meetinghouse. This large open area allowed for much local trade and community interaction. Nearby, stood the Court House and, at the outer edge, the Kent County (Free) School, established by law in 1723. In 1827, a Masonic temple was also constructed. The town, even in these early days, boasted silversmiths, other craftsmen and tradesmen, a rope walk, as well as taverns and inns.

Building a College
In 1780, a Church of England priest arrived from Philadelphia to serve at Emmanuel and take over instruction at Kent School. This erudite man, Dr. William Smith, not only headed a convention in town that renamed the denomination for the first time as the "Protestant Episcopal Church," but quickly undertook, in 1782, to create Maryland's first college, an institution of higher learning. The site Smith selected was contiguous to the old town and after raising the money and obtaining a charter, he quickly began construction of an immense college edifice in the middle 1780s (unfortunately destroyed by fire in 1827), adding greatly to the amenities of the town. The college was in fact named in George Washington's honor, with the general's personal approval.

Later Growth
The years 1860 to 1870 saw a dramatic increase in the Kent County population, from 13,267 to 17,102. The town was divided during the Civil War between North and South, but new entrepreneurs came in, along with the railroad, and there was a wave of prosperity, made evident today by the large number of Victorian style houses and mansions.  The traditional crops were supplemented by a thriving fruit growing and canning industry. The old court house was replaced in 1860 and a quaint row of small lawyers' offices was developed. Some of the early mansions were modified to suit the new taste. The Methodists, strikingly, added two new Victorian Gothic churches on High Street after leaving their earlier meetinghouses. Many of the new homes were built, with 99-year leases, on the hundred acres of land adjoining the town to the northeast, which had belonged to the Kent School and, subsequently, to Washington College.

Around 1900, the public space was tidied up and a park with a popular cast-iron fountain filled much of the space. A new brick public school was built in 1901 on High Street in the increasingly popular Colonial Revival style. Restoration of the Colonial look of the town was inspired in part by the 1876 Centennial celebrations of the Declaration of Independence. The present appearance of the town has a lot to do with that style, along with the restoration of authentic examples.

Modern Developments
The 1930s saw the formal setting up in town of a proper hospital, which has since grown immensely, together with other medical services. This constantly improving nonprofit institution also cares for the citizens of both Kent and Queen Anne's counties. An up-to-date county library building was constructed on High Street in the early 1960s, further adding to the town's amenities. Two modern shopping centers are at the northern edge of town, and the cultural life has been greatly enhanced by programs of Washington College, the Kent County historical society, various arts organizations, as well as antique shops and bookshops.
                                                              
Of course, the life of Chestertown was affected by the opening of the Chesapeake Bay Bridge in 1952.  It all but eliminated boat travel to and from Baltimore.  The town's remote location, at the same time, was a hindrance to tourists, to rapid overdevelopment and, certainly, to regular commuting to Western Shore destinations. The influx of newcomers in more recent years with improved highways has been a mixed blessing: a more diverse, highly educated population seeking the relative peace and quiet has resulted in some loss of social cohesion and caused a significant increase in property values.

The town government, which consists of a Mayor, four councilmen and a Town Manager is kept busy with new projects and increased population. In 2000, the town’s population stood at 4,746 persons but the area now covers about eight times the land first planned in 1730.  Because of these factors and the establishment of Maryland's second Historic District Commission in 1964, which has guided restoration, Chestertown seems ever more popular for retirees and buyers of second homes. Chestertown's virtues are frequently cited in preservation publications, travel articles in magazines, and newspapers from New York to Washington. Indeed, the demand for residence there is now greater than ever--testimony to Chestertown’s long history, riparian location, desirable amenities, and its quiet small town charm.

—Robert J.H. Janson-La Palme, PhD

Professor Emeritus, Washington College