Windsor, Ohio was founded in 1819, and Chesterfield, Ohio, was founded in 1834. In sharp contrast to the Quaker stronghold in Chesterfield, Windsor was a quintessential river town, “wet” in more ways than one. The river men of old Windsor created a booming hamlet with a raucous aspect—fueled, for most of the period, with alcohol in various forms—and unfazed by enmity, politically or otherwise. Windsor was content to be a vibrant river town, and there was never much question about where the town fathers would come down on the issue of alcohol. Windsor stayed “wet” nearly continuously until Prohibition. The hamlet of Chesterfield was “dry.” Three Quaker men—Dempsey Boswell, Elijah Hiatt and Exum Bundy—all with roots in Chester, England, by way of Belmont County Ohio—bought acreage from the Ohio Company and settled in Marion Township and were intent on establishing a peaceful village where they could prosper in business while doing the work of the Lord.
Windsor also had not had much of any experience with slavery. Slaves had never worked the soil in Morgan County, but many passed through on their way to points farther North. In contrast, the Quakers that settled in Chesterfield felt obliged to do much more than simply not engage in the slave trade or help a few runaway slaves now and then. They were compelled to overtly, but peacefully, fight against the peculiar institution that was increasingly tearing at the seams of the Republic. The fathers of Chesterfield presided over a well-organized branch of the Underground Railroad that ran through Marietta, Chesterfield, Malta, McConnelsville, Deavertown, Pennsville, Rousseau, Morganville, Putnam, and points north. These Friends became important links in the Underground Railroad in Ohio. Some acted as conductors and others provided money or housing for slaves as they came through. But whether it was with time, risk, or treasure, the good Quakers provided aid and comfort to runaway slaves without raising their voices or lifting a hand in anger.
The Quaker Church remained a strong presence in Chesterfield, and descendants of some of the slaves that passed through in the antebellum period remained in the area. The Methodists, who settled only a few years after the Quakers and still had a strong presence in Marion Township, went along with keeping the village “dry.”
As time passed, the divide between the two towns diminished greatly, along religious and political lines. By the turn of the 20th century, the only issue that still raised a ruckus between the two towns was liquor. The stark contrast in the handling by the two villages of the alcohol issue was still being played out in the second half of the 20th century. To this day, it is not uncommon to hear variations on the following conversation while attending the Barlow Fair, Fleming Reunion, or the Oakland Homecoming:
“Reba, I hear that your Josephine has a young man. Are they getting serious?”
“Well, Effie, I guess they are.”
“Do you like him? Does he have a good job?”
“Yes to both those questions.”
“You don’t seem very happy about it.”
“I’m just worried a little. He’s from Windsor and works on the railroad. My grandmothers on both sides, good Marion Township folk both of ‘em, always warned me about boys from Windsor.”
“Amen to that, Reba.”
“My grandma said about the same thing. She said that, Windsor boys are go-getters and make a good living, but it doesn’t matter how much they make on payday if they turn around and give it all to the bootlegger on Saturday night.”