From Boston to the Connecticut Valley: Stories of the First Settlers

In 1630, a fleet of seventeen ships set sail from England, carrying about 1,600 settlers to the Massachusetts Bay, a land then largely untamed, where forests stretched unbroken, and rivers ran swift and wild. Among these pioneers were men and women of remarkable energy and resolve: John Winthrop, chosen governor of the new colony, and William Pynchon, a wealthy and educated patentee. Both men carried authority and vision: Winthrop as a political and religious leader, Pynchon as a keen observer of land and opportunity. Settlers joined the small communities already forming in Roxbury, Newton, Dorchester, and Watertown, bringing with them their families, possessions, and livestock into the wilderness.

Pynchon’s curiosity soon led him to explore the Connecticut River Valley. In Roxbury, three Native American sachems brought him furs of beaver, otter, fox, wolf, and mink, describing the valley’s fertile meadows, abundant rivers, and plentiful fish, including salmon, shad, bass, and sturgeon. The richness of this land sparked the imagination of Pynchon and his neighbors. Early scouts such as John Cable and John Woodcock returned with reports confirming the land’s promise, and Pynchon himself undertook journeys westward, evaluating the terrain. Though many settlers hesitated, fearing the unknown wilderness, the bold and ambitious prepared to follow Pynchon to establish a new settlement at Agawam, later named Springfield.

A Mapp of New England, 1675. Map reproduction courtesy of the Norman B. Leventhal Map & Education Center at the Boston Public Library

On May 1, 1636, Pynchon and his Roxbury neighbors departed, carrying their families, livestock, and belongings along what was afterwards called the Connecticut Path. Their journey was arduous. They crossed forests, bogs, and river fords, setting up temporary campfires under towering pines or beside trickling streams. Women and children traveled alongside armed men with matchlock muskets. Despite the dangers, including encounters with wolves and the uncertainties of wilderness travel, the group arrived at their intended location after three weeks without major incident.

Once there, Pynchon and his associates secured the land through formal purchase. On July 15, 1636, a deed recorded thirteen Native American sachems transferring river meadows and upland territories to Pynchon, Henry Smith, Jehu Burr, and their fellow settlers. This first acquisition covered the area surrounding Springfield along the Connecticut River. By 1674, additional purchases, including lands east of the river extending to the mountains, were made by Elizur Holyoke and other settlers, while other tracts to the north along the Chicopee River were secured from the Native Americans Wequaugan, Wawapaw, and Wequompo. Payments were made in wampum and goods, and the deeds documented that while the land was sold, the Native Americans reserved rights for hunting and fishing, provided it did not interfere with English settlements. These transactions laid the legal foundation for Springfield and, later, for towns such as Wilbraham and Hampden.

William Pynchon received the deed giving him title to most of what is now Springfield, Longmeadow, and Agawam. Mass Moments

The region known as the Outward Commons, a broad stretch of land east and west of the Connecticut River, remained largely unsettled for decades. In 1685, Springfield’s town meeting voted to divide these lands among 123 proprietors, including allocations for the ministry and for schools. Surveyors measured the commons in miles and rods, creating divisions to ensure fairness. Each proprietor drew lots in a lottery system for the east and west divisions. Some, like Colonel Pynchon, received thousands of acres, while smaller proprietors might obtain only a few acres. The width of the lots varied based on estate value and number of polls, and the length often extended four miles, from east to west across the commons. These careful divisions created the first structured land ownership in what would become Wilbraham, Hampden, and Ludlow.

The wilderness they inherited was both challenging and abundant. Fires had cleared much of the forest, leaving open pastures. Hills provided summer grazing for livestock, and low, swampy lands supplied coarse winter grass. Wildlife thrived: deer roamed freely across hill and meadow, wild turkeys ran in flocks, and the rivers teemed with salmon, shad, and bass. Beavers built dams on streams such as Pole Bridge Brook, and muskrats were common. Bears occasionally appeared, preying on corn or frightening children, while hunters and settlers alike pursued game to sustain their households.

Few Native Americans remained in this territory by the early 1700s, yet their presence lingered in place names and artifacts. Numerous stone tools, arrowheads, and soapstone dishes attest to generations who had lived and hunted here. One Native woman, Weshaugan, lived alone near a small brook, later called Wigwam Hill, maintaining her wigwam and occasionally interacting with settlers. Stories of her generosity and solitude endured long after her passing, representing the quiet end of the indigenous presence in the area.

Over the 17th and 18th centuries, surveys, deeds, and land allotments gradually converted the wilderness into organized farmland and villages. Streams and ponds were named by distance from Springfield, such as Nine Mile Pond (formerly Manchonish Pond) and Eleven Mile Brook (later Twelve Mile Brook). Roads, paths, and settlements followed these divisions, linking Springfield to the newly settled eastern lands. By the mid-1700s, these lands, once unbroken forest and meadow, were measured, mapped, and legally held by their proprietors, forming the foundation for Wilbraham and neighboring towns.

Through these efforts, the Connecticut River Valley was transformed. What had been a wilderness of towering pines, bogs, and meadows, with roaming deer and abundant fish, became a patchwork of farms, pastures, and villages. The careful surveys, land divisions, and legal purchases established a framework for settlement that shaped the region for generations. The stories of Pynchon, Holyoke, and the early proprietors, alongside the memory of the Native Americans who once inhabited these lands, continue to define the history of Wilbraham, Hampden, Springfield, and the surrounding Connecticut River Valley.