Deerfield is a place of continuity.  The meadows surrounding the village, tilled for generations by Native Americans, are still planted by Deerfield farmers.  The 17th-century English town plan of a compact village and broad meadows is still visible on the landscape and defines the village. Today, 18th and 19th-century houses filled with antique furnishings reveal the lifestyles of Deerfielders from the time of the first English settlement in 1669 to the Arts and Crafts Movement in the early 20th century.

Located near the Deerfield, Green, and Connecticut rivers, sources of rich alluvial soil, Deerfield’s fertile agricultural land attracted English colonists, despite its frontier exposure to French and Indian attack. In the 1660s, the proprietors of the town of Dedham, near Boston, were granted 8,000 acres "in any convenient place" in the Massachu­setts Bay Colony to compensate them for lands occupied by "Praying Indians" at Natick under the missionary John Eliot. The search for the best available land ended at Pocumtuck, and the General Court of Massachusetts granted the future site of Deerfield to Dedham's proprietors. The first settlers, Samuel Hinsdale and Samson Frary, arrived in Deerfield in 1669, and the village and surrounding meadows were divided among 43 proprietors.

The English colonists who settled Deerfield were hardly the first inhabitants of this beautiful valley. Native Americans have lived in Deerfield for at least 8,000 years. When English traders first saw Deerfield in the 1640s, they encountered the Pocumtucks, a small but pros­perous and powerful group of Natives who had farmed, fished, and hunted in the area for generations. Like other Native people, the Pocumtucks suffered from the diseases brought by early English explorers.  Their population was decimated, and then scattered in a conflict with Mohawks in 1665. When the first English settlers arrived, the village of Pocumtuck had been abandoned, although a Native presence in western Massachusetts continues until the present.

The natural topography of Deerfield provided an ideal site for a New England town. At the foot of Pocumtuck Ridge, an intervale about one mile long and one-half mile wide accommodated a compact village in which settlers could live in close prox­imity to one another, work together, worship in their meetinghouse, and defend one another in time of danger. Surrounding the village was vast, open meadowland that flooded each spring, renewing the already fertile soil. Here settlers established a familiar English open-field village. The town plan was remarkably effective and remains well preserved. Houses line the original street, and Deerfield's fifth meetinghouse, the 1824 Brick Church, stands at the center of the village overlooking the original Town Common.

As a frontier settlement, Deerfield regularly suffered from attack. The village was abandoned during King Philip's War after the 1675 attack at Bloody Brook (South Deerfield).  Deerfield was resettled in 1682, only to face several more raids in the 1690s, and the devastating raid of February 29, 1704, when 50 were killed and 112 marched off to captivity in Canada. These early events shaped the community and instilled a keen awareness of the past among generations of its inhabitants who took great pains to preserve and commemorate the village’s unique history.