As in Somerset County, information about roads in Kent County appear as short entries in the court minutes, recorded in (Proceedings) in series C1091, for 1669-1720 and in (Petition Record) in series C1089 for 1739-1757. The proceedings through 1676 appear in the Archives of Maryland. After 1720 the extant minutes gradually become more abbreviated, until by 1731 the record books for court cases no longer contain the minutes. The clerk may have recorded minutes in separate books, but the earliest such surviving record dates from 1774. The petition record contains summary notations about various petitions filed with the county court concerning such matters as new or renewed ordinary licenses, violations of indentures, land boundaries, and roads. 

The court minutes of October 9, 1669 provided the first reference to roads in Kent County and included a fairly extensive list of "highwayes." The public roads consisted of routes from Kent Point to the head of Broad Creek, from this road to the courthouse, from the courthouse to Piggquarter Creek along Gunn Ridge to Isaac Winchester's to the road by Morgan Williams' to Love Point, from the head of Piggquarter Creek to Robert Dunn's house by John Dabb's plantation to William Granger's house, and from Maj. Thomas Ingram's house up the neck by Mark Benton's plantation to the head of Stowells Branch by Robert Dunn's plantation to William Head's to the main road. The 
justices appointed two overseers, one for the Upper Hundred and one for the Lower Hundred.  Their 

names, except for the surname Harris, appeared on missing parts of the page. 

One year later the court ordered the continued maintenance of the same roads, without naming them. Another road, from Pigg Quarter Creek to the road at the head of Broad Creek, was listed along with three bridges that included ones at the head of Pigg Quarter Creek, head of Tarkeele, and spring at Little Neck. John Dabb was designated overseer for the roads in Upper Hundred and Edward Burton for Lower Hundred. 

After these initial entries the sampled minutes contained appointments of overseers, orders regarding roads and bridges, and considerations of petitions filed by individuals. By 1686 the road system required the services of more than two overseers. Appointed then were Henry Carter for the Upper Hundred of Kent Island, Andrew Toulson for the Lower Hundred of Kent Island, Benjamin Ricand and Josias Lanham for Eastern Neck and Swan Creek, and Robert Browne, William Pearle, and John Parson for Langford Bay. The justices could designate an overseer for a specific road, such as John Primrose in 1702 for the road from John Sollers' to the main road to Whitwells Branch to Capt. John Whittington's. 

Sometimes the appointment of an overseer included instructions to establish or maintain specific roads or bridges. In 1686 Josias Lanham, as the overseer for Eastern Neck, was ordered to clear a road to New Yarmouth, build a bridge over Piney Swamp, and clear a path from the "hole in the race" to New Yarmouth through the Narrows to Maj. Wickes'. In 1703 the county court directed the overseer to clear the "straight road" from Morgans Creek by Francis Collins' to the Sassafras Ferry. 

Overseers could be reimbursed for extra expenditures. In 1717 the county judges authorized William Comegys to build a bridge over Toae or 

Descriptions of roads in the records ranged from vague to fairly specific locations. In 1703 Henry Williams had petitioned for a road and was given permission to build a one through the woods, probably wherever he owned land. In 1704, on the basis of a petition from inhabitants at the head of the Chester River, the court ordered William Comegys to clear a road between the plantations of John Ellis and John Toaes and from Prickle Pear Mill to the forest. In 1716 Lambert Wilmer was appointed overseer to clear the road from his house to the head of Cyprus Branch towards Duck Creek and from that route to Black Walnut Branch along the old path leading to Black Birds Creek. 

A description of a road could change slightly over time. In 1716 the justices appointed Thomas Hynson overseer over the main road from Thomas Joce's over the Narrows and through Eastern Neck Island to the place formerly called Oyster Shell Landing. Eight years later the description became the road from Thomas Joce's house to the narrows and over to the Neck to where an old road formerly lay. 

The county justices acted on petitions to abandon roads, alter routes, and establish new ones. In 1694 John Hynson, executor of the estate of Maj. Wickes, wanted a road declared non-public. A roadway went through the land of Maj. Wickes to Love Point that he also had owned, and residents were trespassing by using the road that did not go to a public landing or any other public place. The judges agreed and in essence privatized the road. A more normal request concerned a desire to have a private road declared a public highway. Thus, the county court accepted as public roads the route from Joseph Gleaves' plantation to the mouth of Morgan Creek to Horn Bridge in 1739 and from the head of Morgans Creek to Worton Road in 1743. 

Petitions to change routes usually involved roads through land owned by the petitioners. In 1747 Charles Ringgold filed such a request concerning the road from Swan Creek Bridge to the main Eastern Neck road. He wanted to straighten the route between the bridge at Edward Gibb's plantation to the Swan Creek Road near where Patrick Walters lived. The court accepted his offer to do the work. Some later petitions referred to attached plats which unfortunately were not recorded. In 1748 several residents proposed a relocation of part of the road from Chester Town to the River Bridge and public warehouse in order to shorten the route by 1.5 miles, and filed a plat to demonstrate their plan. The justices authorized construction of a new route from Old Mill Branch in a straight line the bridge and warehouse. 

Blockage of an existing road prompted some petitions for road changes. In 1755 James Dunn was building a mill at the head of the northwest fork of Langfords Bay and the resulting pond would flood the road to the Lower Church. The county court gave him permission to move the road below the dam. A few months later residents living above the Cyprus Bridge complained about Mr. Bordley's tenant blocking their passage to a mill and suggested a new route, accepted by the justices. The change took the road from Duck Creek Road past Joshua Vansant's mill to a new bridge below his mill and across the branch to intersect Queen Anns Road. 

Petitions for new roads appeared less frequently than ones for alterations. In 1739 Christopher Hall, Benjamin Palmer, and Joshua Vansant wanted a market road laid out to the road going to Georgetown. The court appointed Thomas Hynson and James Spencer to review the request and report their findings. The favorable report resulted in the petitioners being ordered to clear and maintain the road. In 1740 Rev. George William Forester asked 
for a road from his chapel to George Town.  Here 

During the search for information about roads in the records of Kent County, the author noted other interesting tidbits of historical data. During the colonial period counties in Maryland were divided into hundreds. Extant records seldom indicate when they were established and usually offer only hints about the boundaries. The (Proceedings) in series C1091 does contain one of these rare notations. In 1703 the justices ordered the creation of a new unnamed hundred in the upper part of Chesters Upper Hundred from the head of Morgans Creek. 

Inclement weather today can cause closings and cancellations. On January 23, 1704/05 the county judges postponed everything for that term until the court sat in March "because of extraordinary bad weather and other inconveniences." 

During court sessions justice could be rendered immediately. In June 1717 William Mackey came into

the courtroom drunk and disturbed the proceedings. The justices ordered the sheriff to put him in the stocks for two hours. 

References to Indian slaves were found in two instances, once in the minutes of the court and another in (Petition Record) in series C1089. In 1717 John Nancoyne brought into court his slave, an Indian girl named Sarah, to have her age determined. The judges decided she was eight years old. In 1745 Indians Will and Hannah petitioned for their freedom, alleging that William Spencer was illegally holding them as slaves. The court set them free and ordered Spencer to pay them 500 pounds of tobacco. 

The last unusual record entailed a petition filed in 1739 for the registration of a house built for worship by Presbyterians on Lot 100 in Chester Town.