Beyond the schools that proudly bear his name, the legacy of Fairfield’s founder, the Puritan leader Roger Ludlow, is complicated. Like all pioneering mavericks, scratch at the surface and history reveals a bold, unyielding and controversial leader who defiantly created a settlement here 375 years ago. Ludlow, also Connecticut’s deputy governor, is credited with drafting the Fundamental Orders, considered to be the precursor to the state’s constitution. “I guess he’s what today we call your classic Type A person,” says Walter Matis, program and volunteer coordinator at the Fairfield Museum and History Center. “He was very driven and had very strong opinions. It’s not a surprise that he basically did write laws that would become the state constitution.”
What contemporary town historians know about Ludlow begins when he crossed the Atlantic from his native England in 1630. A young leader in the Massachusetts Bay Colony, he went on to become one of the founding members of the Connecticut Colony at Windsor and fought the Pequot Indians in the Great Swamp Fight of 1637.
Ludlow epitomized the pioneering spirit and desire for freedom that drew the Puritans here, and with that nature, he and a small party of men were dispatched from Windsor to settle in the Bridgeport/Stratford area in 1639. For reasons that Matis says remain unclear, Ludlow instead put stakes in the four corners area where today Beach and Post roads intersect. While he was censured by the General Court and fined a hefty 50 pounds for not fulfilling his settlement orders, Matis says there’s evidence that “Ludlow believed he was acting within the spirit of their directive” when he chose Fairfield.
Ludlow eventually left after a scandal. In 1653 Goodwife Knapp was convicted for being a “witch.” Matis says lore has it that at the hanging scaffold, she whispered to Ludlow that his neighbor, Mary Staples, was a witch. Mary’s husband, Thomas, had helped Ludlow settle Fairfield and the two were in a protracted feud. After Mary was acquitted, the Staples sued Ludlow for defamation. Ludlow left town in 1654.
Ludlow eventually returned to England, presumably taking his family and the personal artifacts that would have illuminated the historical record, says Matis. “As much as we do know about him, there’s so much we don’t,” he says. Matis stresses that Ludlow’s departure must be considered in a broad historical context. His ambitions may have been to use experiences here to advance himself in England. “Many of those who came here had aspirations to eventually go back,” Matis explains. “They came here not only for freedoms and prosperity, but to prove things back home. Nothing that occurred in the colonies really happened in a vacuum.”
Ludlow served as a magistrate under Oliver Cromwell after conquering Ireland but then little is known. “No one is even sure if or where he’s actually buried in Ireland although that appears to be where he stayed,” says Matis.