Introduction: After the founding of Chestertown as a port in 1706, Kent County became firmly established as a center of farming, trade, travel and culture within the region. Skilled craftsmen set up shop in the new town, taverns thrived as centers for news and politics, and merchants profited from Chestertown’s rapid growth. Horse races, theater and balls brought ladies and gentlemen, as well as students from Washington College, to town. In the outlying areas, mills, shipyards, plantations and water crossings were the center of activity. Although roads were poor, the shortest route between Virginia and Philadelphia brought travelers through the county, across from Annapolis on the Rock Hall ferry. By the time of the Revolution, Kent County was poised to take a position of prominence as a political and supply hub during the war.

FOUNDING OF CHESTERTOWN: In 1706, Chestertown was founded under the Act for the Advancement of Trade and the Erection of Ports and Towns. The "New Town" was laid out along the Chester River on land belonging to Thomas Joyce, once part of Simon Wilmer's "Stepny." The Act spurred town growth and diversification by exempting skilled craftsmen from taxes for four years if they moved into the town. It also said that all orphaned males must only be apprenticed to town craftsmen.

By the 1730's, Chestertown was thriving. Kent County's enterprising class of planter-merchant families, many now in their third generation, were not only skilled in maritime trade, but also were the first to lead Maryland planters away from the fluctuating market of soil-exhausting, labor-intensive tobacco, into a grain-based, more diversified economy. Their sleek, locally built craft—single-masted sloops and two-masted schooners—slipped from the harbor at the end of High Street, carrying flour, salted pork, and tobacco to the West Indies, Spain, the Azores and Madeira, and returned with fruit, wine, and salt. Warehouses and commercial buildings were built, as well as the solid brick manor houses still in evidence today.

Many residents, now newly prosperous, began to complain of the old ways: “…Swine are so numerous that they break into warehouses where grain is stored, and the inhabitants cannot preserve their gardens from being destroyed by them.” New laws were passed so that livestock could no longer roam freely in the New Town of Chester. 

Colonial Travel: Colonial Kent County offered the shortest route between Virginia and Philadelphia, and on to points north. Travelers crossed the Bay from Annapolis on the Rock Hall ferry, rode or took a stage through thriving wheat fields, by farms and mills, past old St. Paul's, into Chestertown for a night's rest, then on past Shrewsbury Church, through Downs Crossroads (Galena), then crossed on another ferry at Georgetown and on into Delaware.

Traveling in the colonies was rough; early roads were often no more than wide, muddy paths and few ferry crossings offered shelter to the traveler from whipping winds and rain.

Nevertheless, our Founding Fathers made the trip often. George Washington, Thomas Jefferson, James Madison, and Patrick Henry all traveled through Kent County on their way to make history.

George Washington Slept Here: The Father of our Country made eight trips through Kent County. The first was in February 1756 to see the Governor Shirley of Massachusetts; and the next year, he went to visit Virginia governor Lord Loudon in Philadelphia. Both journeys were to ask for a royal commission in the British army rather than that of a lower ranking Colonial officer. The fact that he was unsuccessful in this mission may have influenced his next two trips through Kent County.

Washington's 1773 trip through the Eastern Shore was a personal one. He was on his way to enroll his stepson at King’s College in New York. From Washington’s diary entries we learn that on “13 [May]. After Breakfast & abt. 8 Oclock set out for Rockhall where we arrivd in two hours & 25 Minutes. Dind on board the Annapolis at Chester Town & supped & lodgd at Mr. Ringolds.” This was the  Hynson-Ringgold House on Water Street, where his hosts were Thomas Ringgold IV and Mary Galloway Ringgold.

In the fall of 1774 Washington attended the First Continental Congress in Philadelphia. Arriving at Rock Hall on September 2, he “lodged at New Town on the Chester.” The next day he rose early to “Breakfast at Down's (Galena)." On the return trip on October 28, Washington once again "dined at Down's & lodged at New Town upon Chester.”

Perhaps Washington’s most famous visit to Kent County occurred on May 19, 1784. He stopped in Chestertown on his way home from Philadelphia to join the Board of Visitors and Governors of the College that bore his name, and was honored by the students, faculty, board and townspeople before departing early the next morning for Rock Hall and eventually Mount Vernon.

Washington’s last trip occurred in September 1791 during a Presidential tour of the South. He dined and lodged at Worrell Tavern in Chestertown, and then traveled to Rock Hall to take a boat across the Bay. As he records in his Diaries, the “night being immensely dark with heavy and variable squalls of wind—constant lightning & tremendous thunder” the ship ran aground twice, before finally reaching Annapolis. He never came to Kent County again.

Taverns: Taverns or “ordinaries” played a key role not in only travel, but also in community and political life. In them, news and gossip were exchanged, politics discussed, business conducted, and sometimes wars plotted. The taverns provided points of connection within the Colonial world.

Establishments that welcomed residents and travelers in Kent County with a blazing fire and a stiff drink included the Rock Hall Inn, (which may have given the town its name), and Daniel Toas’ ordinary at the Head of Chester (Millington). In Chestertown there was Worrell's; Nicholson's (now the White Swan Tavern); and the infamous Dougherty's on High Street.

As a visiting Scot wrote in 1744: "…[I] reached Newtown and put att Dougherty's, a publick house there. I was scare arrived when I met severall of my acquaintance …and dined att the taveren where I was entertained by the tricks of a female baboon in the yard…and treated by Captain Binning of Boston with a bowl of lemmon punch…whiele we put about the bowl, a deal of comicall discourse passe'd in which the landlord, a man of a particular talent att telling comic storys, bore the chief part."

Henry Clay, the proprietor of Dougherty’s [not Walter Dougherty?], was an enterprising businessman who had originally purchased his freedom from Thomas Smyth. He had a license to sell "good West Indian rum, good cider, and Madeira wine," at a concession for the popular horse races at Downs Crossroads.

Colonial Laborers: Country life centered around mills, shipyards, water crossings and plantations. Hired free men and women, bond servants and slaves were all engaged in enterprises such as planting, weaving, carpentry, smithing, animal husbandry and dairy work. While some planters operated their own mills to process local wheat into flour (which shipped better than the grain), Radcliffe Mill outside of Chestertown was run by James, a slave of Rebecca Wilmer. James was promised freedom in Wilmer’s will, on the condition that he continue to operate the mill for her family.

The sale of men and women and their services was a constant of the Chesapeake’s early economy. The sales included not only slaves, but also indentured servants, and convict labor. Throughout the 1700's, Maryland and Virginia imported more slaves than any other mainland British colony; in Chestertown, slaves were still being imported as late as 1770. After importation was outlawed, the Eastern Shore became a major supplier of slaves, since any man, woman or child who had been born into slavery was considered private property.

Of the 30,000 convicts who came to the North American mainland between 1718 and 1776, more than two-thirds came to the Chesapeake. Between 1746 and 1776, more than one-quarter of all immigrants to this area were convicts. Like slaves, they were bought and sold at auction, and any runaways hunted down and punished.

Trades and Crafts: As the economy shifted from the import of European goods to the fledgling colonies, to the self-sustaining production of American goods, skilled workers became more commonplace, and a strong middle class evolved. In Chestertown, as in Philadelphia and Annapolis, cabinet and furniture makers, silver smiths, clockmakers and other craftsmen began to supply many of the fine pieces once available only through British trade.

Blacksmiths, rope makers, barrel makers, carpenters and dry good salesmen enhanced the local economy. Many engaged in multiple enterprises. James Piper, was not only a merchant and clockmaker, but also ran a tavern, a store and a ferry service to Baltimore.

Powerful planter-merchants owned, and sometimes built their own ships, working closely with merchants in Baltimore, Annapolis and Philadelphia. The homes of such influential figures as Thomas Ringgold and Thomas Smyth still stand today. These men and their colleagues would become significant players in the American Revolution.

Colonial Culture: Chestertown became a colonial center of cultural activity as well as trade. Kent County residents and visitors enjoyed theatrical performances that included The Beggars Opera and The Lying Valet, and "David Douglass and His Company of Comedians." Soon after its founding, Washington College inaugurated a tradition of public performances, including Gustavus Vasa for the 1784 visit of George Washington.

Purse and cup horse races were staged in fall and spring. Horse racing was a popular colonial sport, drawing large crowds from surrounding towns with some people traveling from as far away as Philadelphia to enjoy the festivities. Dress balls were held in which both ladies and gentleman appeared in the latest elegant fashions. A portrait of the colonial society can be found in the letters of Molly and Henrietta Tilghman of Chestertown, written in the 1780s.

Religion: After an "Act for the Service of Almighty God and the Establish of the Protestant Religion" established the Church of England as the official Faith of Maryland in 1692, the vision of religious freedom for Catholics, Quakers, Puritans, and Presbyterians of the colony began to erode. All property owners were now taxed quantities of tobacco for the support of the Anglican Church and its clergy.

On the eve of the Revolution, the required oath of allegiance by Anglican clergy to the British Crown caused obvious difficulties for the church. William Smith, the founder of Washington College and rector at Chester Parish (now Emmanuel Church) played a leading role in a series of conventions of Maryland clergy held in Chestertown, Baltimore and Annapolis in the 1780s, from which the Protestant Episcopal Church emerged.

At the same time, Methodism was on the rise on the Eastern Shore. Their scorn for vanity made them natural opponents of the planter class, and at their 1784 Conference, they voted to join with the Quakers in the abolition movement. (The Quakers had been called to free their slaves as early as 1778.) Later, Methodists would turn their back on the abolitionist movement as entrenched bigotry began to cause their membership to decline. Meanwhile, African American Methodists established their own churches.

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