Through the Ravines: Wilbraham and the Road to Freedom

In the first half of the nineteenth century, as the nation wrestled with the growing conflict over slavery, Wilbraham and South Wilbraham became quiet participants in one of the most dangerous and morally driven movements in American history, the Underground Railroad. Though no signs marked its presence and few written records were ever kept, the town’s geography, churches, and individual residents combined to make Wilbraham an important link along the eastern route to freedom.

An illustration of a family escaping slavery, risking everything for freedom. history.com

The Underground Railroad was not a railroad in the literal sense, but a loosely organized network of people who offered shelter, guidance, and transportation to enslaved men and women seeking freedom. In western Massachusetts, much of this effort centered on Springfield, a key river city with strong abolitionist sentiment. The director of Underground Railroad activity in the Springfield area was the Reverend Samuel Osgood, pastor of the First Church in Springfield from 1809 to 1854. Through his long tenure, Osgood became a central figure in coordinating assistance, relying on trusted individuals in surrounding towns rather than any formal organization.

From Springfield, freedom seekers typically traveled eastward away from the Connecticut River or moved northward from Connecticut into Massachusetts. Wilbraham’s position along this route made it a natural passageway, part of what was considered the main line heading east. The town’s rural character, scattered farms, and lightly traveled roads allowed movement to take place largely unnoticed, especially under the cover of darkness.

Equally important was Wilbraham’s landscape. The Glendale sections of both Wilbraham and South Wilbraham were characterized by steep ravines, thick woods, and uneven terrain. These natural features provided ideal hiding places during daylight hours. Fugitives could remain concealed in wooded hollows and ravines while waiting for nightfall, when it was safer to move. The land itself became an ally, offering protection that no building or person alone could provide.

Within this setting, individual residents stepped forward to help. Among the most notable were John Calkins, a shoemaker in South Wilbraham, and his wife, Lucia Day Calkins. The Calkinses are recognized as leaders in Underground Railroad activity in this immediate area. Like many involved, they were ordinary citizens whose daily lives gave little outward indication of their dangerous work. Their home served as a point of refuge, where fugitives could rest, receive food, and gather their strength before continuing their journey. The assistance they provided required careful planning, secrecy, and a network of trust that extended beyond Wilbraham’s borders.

Some homes in Wilbraham and South Wilbraham were constructed or adapted to include concealed spaces, including hidden basements or false walls. These spaces were used as temporary safe havens, allowing freedom seekers to remain hidden during daylight hours when the risk of discovery was greatest. Harboring fugitives was illegal under federal law, particularly after the passage of the Fugitive Slave Act, and those who participated faced fines, imprisonment, or worse. Despite these risks, residents continued their efforts, motivated by conscience rather than compliance.

Churches in Wilbraham and South Wilbraham also played a quiet but influential role. While not all congregants agreed on the issue of slavery, abolitionist ideas were discussed from pulpits and in private homes. Ministers and parishioners alike contributed to a climate in which assisting fugitives was seen by many as a moral obligation. This shared belief helped sustain the secrecy and cooperation required for the Underground Railroad to function.

Because secrecy was essential, few firsthand accounts survive, and much of what is known comes from later recollections, local tradition, and the identification of known participants. This absence of documentation is itself evidence of how seriously those involved took the need for discretion. What can be said with confidence is that Wilbraham and South Wilbraham were active links in a larger chain of resistance to slavery, connecting Springfield and Connecticut to points farther east.

The legacy of the Underground Railroad in Wilbraham is not marked by monuments or plaques, but by the actions of its residents and the landscape that sheltered them. In wooded ravines, quiet farmhouses, and unassuming village homes, individuals chose to risk their safety to help others claim their freedom. Though largely unspoken for generations, this chapter remains a significant part of Wilbraham’s history, one defined not by public recognition but by quiet courage and moral resolve.