circa 1720 ♦ 566 Boston Post Road
One of the oldest buildings in Madison, the Dudley House at 566 Boston Post Road was constructed between 1670 and 1720 and received a visit from General George Washington in 1776. The house architecture is typical of a late first-period center chimney house and the house’s interior features an exposed timber frame common to houses of the late 17th century and early 18th century. The house’s interior is organized into three sections. Two large rooms flank a smaller central room that contains the entryway, stairs, and chimney. The two large rooms are the hall and parlor. Colonial-era families used the hall for various purposes including cooking, eating, and other daily activities. On the other hand, families usually reserved the parlor for welcoming special visitors and displaying the family’s valuable possessions. The house also features a basement that was used to store foodstuff. The stairs to the basement allowed the residents to bring food and supplies to the hall without bringing them through the more formal parlor. In the early 20th century, the house was moved back from the street. As a result, the basement’s location relative to the house and flooring differ from their original form.
Deed records indicate that Thomas French gave 20 acres to and constructed a house for his daughter, Martha Dudley, and son-in-law, John Dudley, sometime around 1675. John Dudley was born in London and impressed into the British Navy. Dudley escaped to Boston before arriving in Guilford in 1673. In 1673, Dudley married Martha French, who was born on August 6, 1654. John and Martha Dudley had seven children: John (b. 1675), Mary (b. 1678), Nathaniel (b. 1680), Ebenezer (b. 1682), Mercy (b. 1684), Jonathan (b. 1686), Elizabeth (1688). After John Dudley died in 1690, Martha Dudley gained possession of the property and, sometime between 1690 and 1710, gave ownership to her son Ebenezer Dudley.
Although no records exist of the date on which Ebenezer Dudley received the property from his mother, he probably received the property in 1700 when he turned 18. In 1704, Ebenezer married Abigail Kelsey. During their marriage, Ebenezer and Abigail Dudley had four children: Martha, who was died less than a month after her birth in 1706, John (b. 1707), David (b. 1709), and Ebenezer (b. 1710). In 1710, Ebenezer Dudley gave the Dudley House to his brother, Jonathan Dudley, in exchange for other lands in the region. After leaving 566 Boston Post Road, Abigail Kelsey died, and Ebenezer Dudley remarried in 1713. Dudley’s second wife, Elizabeth Graves, bore him five additional children: Mary (b. 1714), Elizabeth (b. 1716), Abigail (b. 1719), Nathaniel (b. 1721), and Sarah (b. 1723).
At the time of Jonathan Dudley’s acquisition of the Dudley House, his mother and brother, Nathaniel Dudley, still owned parts of the property. Throughout his lifetime, Jonathan Dudley acquired property from family members and eventually owned the 20 acres that Thomas French had given to John Dudley. On August 6, 1712, Jonathan Dudley married Abigail Munger, who was born in 1792. Jonathan and Abigail Dudley had 11 children: Abigail (b. 1716), Martha (b. 1718), Naomi (b. 1719), Jonathan (b. 1721), Elizabeth (b. 1722), Temperance (b. 1724), Simeon (b. 1726), Elizabeth (b. 1727), Temperance (b. 1730), Mary (b. 1932), and Gilbert (b. 1736). Two of the Dudley children, Elizabeth and Temperance, died during childhood, a common occurrence in colonial America. After Elizabeth and Temperance died, the Dudley named their next two daughters after their deceased daughters, also a commonplace act in colonial America. When Jonathan Dudley died in 1750, he left 566 Boston Post Road to his youngest child, Gilbert Dudley.
Gilbert Dudley married twice. His first wife, Ruth Crampton died on December 18, 1760, at the age of 20. Five years later, Dudley married Sarah Bartlett on November 21, 1765. Born in 1738, Sarah Dudley bore four children: Sarah (b. 1766), Ambrose (b. 1769), Gilbert (b. 1773), and Ruth (b. 1776). During his ownership of the Dudley House, Dudley converted the house into the Gilbert Dudley Tavern and served as a captain in the Connecticut State Militia during the Revolutionary War. On April 11, 1776, Dudley hosted numerous distinguished guests as General George Washington and his staff dined at 566 Boston Post Road. Washington and his staff were traveling from Boston to New York and had heard that a British fleet was anchored in the Long Island Sound. Washington and his staff had a clear view of the Long Island Sound from the tavern because the land between the tavern and the Long Island Sound was cleared. On December 26, 1802, Dudley died and left the property to his son, Ambrose Dudley.
Ambrose Dudley inhabited 566 Boston Post Road until he died on December 22, 1835. Dudley married Mabel Murray and had seven children: Clarissa (b. 1794), Julia Ann (b. 1798), Ruth (b. 1801), Gilbert (b. May 1, 1803), Horace (b. May 1, 1803), Horace (b. 1806), and William (b. 1809). Gilbert and Horace were twins but only Gilbert survived as Horace died less than a month after his birth. When Ambrose Dudley died, his unmarried children, Julia Ann and Gilbert, gained possession of 566 Boston Post Road.
Julia Ann and Gilbert Dudley both never married and inhabited the Dudley house until their deaths. During their ownership of the property, their aunt, Sarah Lee, lived with them and Eliza Hand and Jemima Scranton also inhabited the property. Hand and Scranton’s reason for inhabiting the Dudley House is unknown. Gilbert Dudley, a teamster who rented out his horse and wagon, died in 1864 at the age of 61. Julia Ann died on March 12, 1876, at the age of 77.
After Julia Ann Dudley died, Sherman Buell purchased the Dudley House for $925 before selling it to George Augustus Wilcox a few months later for $1000. George Augustus Wilcox was born on September 20, 1830, to Jonathan Samuel and Chloe Hand Wilcox. George Wilcox attended Lee Academy and studied law at Yale. After graduating from Yale, Wilcox worked as a lawyer in Georgia and Detroit before returning to Madison. During the 1890s, Wilcox purchased several other properties in Madison. In 1926, three years before his death, Wilcox gave 566 Boston Post Road to his daughter, Constance Wilcox Pignatelli.
Constance Wilcox Pignatelli sold the property to Jane Dunn, later known as Jane French, in 1935. French sold the property to Gail M. Snow in 1985 for $250,000. Snow owned the Dudley House until he sold it to its current owner in 2016.