The Woolford Family Tree

For Wayne Woolford, learning about his family ancestry was a “labor of love” that spanned a decade. Recorded for his grandchildren, Wayne chronicles the journey of his colonial ancestors so his grandchildren remember “that your very existence and that of your families to follow are indebted to those ancestors that came before,” he wrote.

His “booklet,” which is roughly 100 pages, travels back in time to the year 1660 and begins with the life of his ninth grandfather, Roger Woolford. To put things in perspective, Roger was one of 50,000 English colonists in the New World in the year 1660.

Wayne Woolford holds a painting of John’s Point in Dorchester County that was home to the Woolford family for over 100 years. He holds an original brick from that home, which is thought to be the first brick home built in what is now America.

The Woolford patriarch Roger Woolford married Mary Denwood in 1660, and together they arrived in what is now Somerset County, Maryland in 1662. He was rewarded land from Lord Baltimore Cecil Calvert there. He belonged to a select group of men that were among the most influential families of 17th century Maryland. Records from 350 years ago are scant, Wayne explains, but it is known that Roger was a Chief Justice in Somerset County and served in the House of Burgess as a delegate for many years. He also helped establish an infrastructure of roads within the county. Roger died in 1701 but, with his wife Mary, they created a family that gave life to all Woolfords in colonial America.

His son, Colonel Roger (1730-1793) married Elizabeth Ennalls, whose family would become the single largest landowner in Maryland with property that extended from Cambridge to Vienna. They settled in Dorchester County at John’s Point, known to be the first brick home in the country. The home was built in 1660 and served as the Woolford family home for generations. It served for a short time as Dorchester’s courthouse as well as a jail on occasion. It burned to the ground in 1856 due to an overturned oil lamp. Wayne was able to secure an original brick from John’s Point from a previous landowner. As bricks weren’t then made in Colonial Maryland as of yet, they were used as ballast in a ship from England and used to build the home.

Colonel Roger was instrumental in the creation of what is today known as St. John’s College, the third oldest school of higher learning, following only Harvard University and the College of William & Mary. He also served in important positions including justice of the court and Burgess in Dorchester County as well as a sheriff.

A direct descendant of Wayne was a Revolutionary War hero, and the most decorated one in Dorchester County from the War for Independence. Lieut. Colonel Thomas Woolford (1754-1841) fought alongside Captain Thomas Sumter and against Lord Cornwallis. He is buried in Woolford.

Wayne says he was “lucky” with his research since so much about his forefathers was well chronicled due to their early involvement in Colonial America. “I was blessed with a lot of information and great resources were available to me about my family,” Wayne admitted.

Resources are key in any ancestorial search. Wayne had successful visits at the Maryland State Archives in Annapolis; the Maryland Historical Society, George Peabody Library and Enoch Pratt Free Library, all in Baltimore; Dorchester County Public Library and Dorchester County Historical Society in Cambridge; and Talbot County Free Library in Easton.

While Wayne focused his research on direct descendants of his lineage, interesting tidbits emerged about his grand uncles and others.

From 1813 to 1963, hundreds of steamboats plied the Chesapeake Bay. Probably the most famous of the Bay steamboats was the Emma Giles. She traveled from Tolchester, down the Bay to Milton Wharf, on Church Creek, near the Old Trinity Church in Dorchester County. Captain of the steamboat Emma Giles for a decade or more was Captain Lee B. Woolford (1862-1933). He is buried in Woolford as well.

Cator Woolford (1869-1944) moved to Georgia and formed a credit bureau there with his brother Guy. Today, we know that company as Equifax. Cator also served on the Georgia Warm Springs Foundation where President Roosevelt and he became friends. Cator is buried in Woolford.

Wayne’s search into the Woolford family begins in 1660 as very little is known about Roger Woolford’s life before he came to Colonial America. Even his birthdate is uncertain. Wayne was able to link the Woolford family back to 1066 when a member of the Woolford (then spelled Walford) family joined William of Normandy at the Battle of Hastings during the conquest of England. Walford Castle was the family’s “address” in those days. What is known with certainty is that the Woolford family lineage is still going strong today. The 10th generation of Woolford grandchildren are young adults now, striking out on their own, and wouldn’t Roger and Mary Woolford be so proud to know.

Family Ties

Do you have an interesting story about your family lineage? For example, Attraction’s owner/publisher, Allison Rogers, is related to Edgar Allen Poe. Attraction editor, Jennifer Latham, has ties to historic Handsell in Dorchester County. She also found out quite by chance that an Easton acquaintance shares her family lineage from Connecticut. We would love to hear about your family ties here on the Mid Shore. Write to Jennifer at

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