Founded in 1642 and named after the Shire of Kent in the West of England, Kent is the mother county on the Eastern Shore. It may be the only county in Maryland to have given up its founding site, Kent Island, when its boundaries were finalized in 1706 concurrent with the establishment of a new seat for government at what is today called Chestertown.

Kent County comprises 284 sq. mi. of land. According to the 2000 census, it has 19,000 residents. Eighty percent of the land is under agricultural use. Sassafras River to the north, Chester River to the south, Chesapeake Bay to the west and Delaware to the east form Kent's boundaries. It is a peninsula accessed by several bridges over the above named rivers and a few roads traversing from neighboring New Castle and Kent counties in Delaware. But these boundaries fluctuated greatly between 1642 and 1706. Progressing northward onto the mainland, early patents were issued on Kent's Eastern Neck Island and soon up toward Rock Hall as well as on Quaker Neck during the latter part of the seventeenth century. Towns as we know them were unheard of prior to laying out Kent's first county seat, New Yarmouth on Grey's Inn Creek.

There are few vestiges of this first town today. New Yarmouth was laid out on 100 acres of James Ringgold's manor, Huntingfield. By 1678 New Yarmouth was an active trading port, with houses, St. Peter's church, a courthouse, jail and taverns. Other settlers ventured farther north to the shores of the Sassafras and established "Shrewbury Town" on its southern bank, likely in the vicinity of John Smith's first venture onto dry land in the upper bay. This second town pushed Kent's boundaries inland and northward. However, with the later establishment of Cecil (out of Baltimore County) and Queen Anne's out of part of Kent and Talbot, Kent's final boundaries were set.

Blessed with ambition and enriched by religious tolerance, Kent's founders worked agriculture, shipbuilding, and domestic crafts to great success. Small landholders achieved a moderate level of well-being, providing for their families and shipping excess crops or trading for goods not readily available in the decades of settlement. Roads were slow to be built. Shipbuilding quickly became a craft among early inhabitants. A significant portrait of this industry was removed from Spencer Hall on Eastern Neck in the early twentieth century and may be seen at the Maryland Historical Society. Numerous ship types are depicted upon this overmantel painting.

Several factors contributed to the abandonment of New Yarmouth and the founding of Chestertown. Primary among them was the increased settlement of the county's interior, making travel for court purposes less and less convenient. The Maryland legislature mandated that a new church be added to St. Paul's Parish, and the earliest church, St. Peter's, disappeared. Midway between Shrewsbury Parish, ca. 1692, and St. Paul's near Fairlee, Chester Parish was seated and is now known as Christ Church I.U., a predecessor of Emmanuel Parish in Chestertown.

In 1706, "New Town" was officially founded and designated as the Port of Entry for Kent on the Chester River. A courthouse was built and the residents of New Yarmouth relocated upriver. A conjectural model of New Yarmouth, the site of which is now underwater, can be viewed at the Rock Hall Museum. Throughout the eighteenth century, tobacco, grain and timber were exported in great quantities from Kent's many landings on both rivers and their tributary creeks.

In colonial times, travelers from the south crossed the Chesapeake Bay from Annapolis to Rock Hall where they boarded a coach for points north. This route brought eminent men, including the first four presidents of the fledging United States, to Kent County whose hospitality provided lodgings and a change of horses to complete the journey. The first news of the American victory at Yorktown was carried through Rock Hall to the Continental Congress, then meeting in Philadelphia. Tench Tilghman rode on horseback through Kent spreading that news. In 1814 the only land battle on the Eastern Shore took place near Tolchester where the Kent militia, led by Philip Reed, defeated the attacking Royal Navy, killing Sir Peter Parker at the battle of Caulk's Field.

The shift away from tobacco as the medium of exchange and the silting up of the Chester River making Chestertown inaccessible to deep draft vessels contributed to the town's decline. With the advent of the railroad on the Delmarva Peninsula and advances in road building, commerce with Kent's neighbors replaced trade by ship. Crop production switched to fruit and grains and most landowners produced far more than they would need, thus creating a commodity to supply the larger cities within a day's travel.

In 1840 Kent County's population totaled 10,842. There were approximately 5,600 whites, 2,491 free "coloured" and 2,735 slaves. At that time, there were five significant towns: Chestertown, Rock Hall, Millington, Georgetown, and Galena, and numerous villages including, Massey, Head of Sassafras, Lynch, Still Pond and by 1850, Kennedyville. The railroad created clusters of dwellings adjacent to such stops as Lambson's, Hepbron, Black's and Worton. The goal of extending branches off the main line to reach Rock Hall and Tolchester never was realized.

The Civil War created turmoil in previously tranquil, rural Kent County. As with other border states, families were divided and lines of allegiance were drawn. Slavery's role in the economy of Kent County had been declining since the labor-intensive tobacco crop was replaced and agricultural industrialization progressed. At the time of the Civil War the number of free blacks almost equaled the number of enslaved African Americans. The free black population included entrepreneurs, tradesmen, educators, and clergymen. Some free blacks worked land they owned and raised their crops alongside white farmers. Over 400 black Kent citizens fought for the Union with the U.S. Colored Troops.

Education in Kent County took root from the Kent Free School, the forerunner of Washington College, founded in 1782 immediately following the American Revolution. By the late nineteenth century a network of one-room school houses had been built for white children throughout the county. Public education was often interrupted, particularly for boys. Their valued labor in family farming ranked higher than book learning. It was atypical to complete eleven years of schooling well into the twentieth century, with girls spending more time in the classroom than their male counterparts. When public schooling for blacks was legislated in the early twentieth century, numerous one-room "colored schools" were built by blacks for their communities' children. Oral histories inform that the teachers were all African American and school supplies were derived from worn textbooks discarded from white schools. As was the case for white schools, the families in each community provided fuel for the woodstoves and living accommodations for the local teachers, all of whom were unmarried women. In time most of the one-room schools were either torn down or converted to residences.

Following regional practice, Kent County's towns all had small grocery stores, some of which are still standing. A very few examples, such as that found in Still Pond, continue to meet the village's needs for which they were built. The local stores now serve other purposes or are boarded up. Transportation of goods on improved highways and the availability of automobiles made centralization of services possible. Larger grocery stores drew patronage from around the county and could out-price smaller enterprises. Eventually even the large, independent grocers were displaced by chain stores in Chestertown such as the A&P. A similar pattern evolved for much retail.

World Wars I and II called for the military sacrifices of Kent's young men, and the home front changed with the creation of a local chapter of the American Red Cross in 1918. A National Guard Armory was built south of Chestertown. During the latter war, a munitions plant was built near the Washington College campus and many women found employment there doing valuable but dangerous work. In 1954 a tragic explosion took the lives of nine women and one man working at that plant. By that time, Kent's small hospital, now known as Chester River Hospital Center was able to treat the injured who suffered from burns, shock and other trauma.

This event among others, as well as several notorious crimes, made headlines. The nineteenth and twentieth centuries were well covered by assorted newspapers in Kent County. From a high of three during the 1920s through 1950s, Kent is now served by a weekly known as the Kent County News and a biweekly, the Tidewater Trader. The economy grew to include pleasure boating and marinas to meet the needs of power and sail boat owners. Local watermen, a mainstay of the upper shore economy, found themselves hard pressed to make a living faced with declining numbers of oysters, rockfish and an imperiled crab population.

Following the integration of public schools mandated in the late 1960s, the number of schools in Kent County declined. Most notable was the closing of Henry Highland Garnet School in Chestertown. Garnet, born in Kent, was a former slave and abolitionist contemporary of Frederick Douglass. Prior to desegregation, this school was the only secondary school for all of Kent County's black children. From an era when Rock Hall, Galena, Betterton, Millington and Chestertown each had high schools, by the early 1970s, school consolidation saw the closing and demolition of numerous school buildings. The sole high school is now located in Worton about the geographic center of the county. With few types of heavy industry to be found in Kent, recent and current graduates of the consolidated high school have often had to leave the area to find employment. A revitalized program of vocational-technical instruction is aimed at filling the occupational roles in high demand in this rural area.

Kent County's location offers proximity to major population centers while at the same time sheltering it from overmodernization. Change has been slow to come to Kent County, in part due to early geographic and transportation isolation. This is not generally regarded as a negative. At the end of the twentieth century, it was recognized that Kent has an aging population with the loss of career initiators graduating from local schools. Simultaneously the vitality of the community has grown noticeably as career-ending retirees are finding the pace of life, views, sense of place, rich history and availability of arts, education, and health services well provided for here. County government in 2004 is in the hands of its second African American council president, William Pickrum. Kent County newcomers report their chosen county's main asset is the friendliness of its people. Though in existence for over 350 years, the assets of the county continue to make its quality of life ever more appealing.