The land on which the Josiah Day House stands was part of a 6-acre lot originally granted to Thomas Day in 1663. The property changed hands several times and eventually became the property of John Pynchon, the largest landholder in Springfield.

In 1696, the General Court in Boston allowed "The residents on the West Side of the Great River to settle their own minister". Two years later a 3-acre parcel of Pynchonís land was purchased and given to Reverend John Woodbridge, the first minister. The 3-acre parcel was given outright to Reverend Woodbridge and it was on this land that he built his house.

A falling tree limb killed the minister in 1718 and his property passed to his heirs who, in 1746, sold it to a weaver named Josiah Day. When Josiah Day married his second wife, Hannah Ingraham, he undertook extensive rebuilding of the original house. Tradition suggests that it was during this rebuilding that Day converted the house into this brick "saltbox". Josiah preserved the old Woodbridge kitchen with its 17th century paneling and walk-in fireplace with bake oven. Both of these features are still part of the house today.

Josiah Day and his direct descendants lived in the "Old Day Place" for over 150 years. In 1903 the last of the surviving "Day Sisters" sold the house to the newly formed Ramapogue Historical Society with the stipulation that it be used as a museum.

For the past 100 years the Ramapogue Historical Society has maintained the "Old Day Place" as a museum dedicated to the Day family and their contributions to the development of West Springfield. For a small fee, the house is open to visitors by appointment and on special occasions throughout the year.