The story of Sarah Dillingham Caldwell, wife of John Caldwell is the record of a loving and most thoughtful life. Born in 1634, the daughter of John and Sarah (Caly) Dillingham, she was one of the first children born in the small settlement before it was named Ipswich. Her father died less than a year after she was born. The mother died two years later, leaving the child in the care of Mr. Richard Saltonstall and Mr. Samuel Appleton. At nineteen years of age she became the wife of John Caldwell, ten years her senior. The years entrusted her with eight children who tradition tells us grew to be worthy people.

In her widowed old age, her son Dillingham and his wife Mary (Hart) cared for Sarah, which she acknowledged by willing them a part of her homestead for sixty-seven years. The First Period home of Sarah and John Caldwell still stands at 33 High Street.

Cotton Lace reported to have been made by “Goody Caldwell” at the Ipswich Museum. Tradition informs us that Sarah Dillingham Caldwell and her descendants were among the early lace-makers of Ipswich.

The Caldwells of Ipswich

Over a hundred descendants of John and Sarah Dillingham Caldwell are buried at the Old North Burying Ground and the Old South Cemetery in Ipswich. Several of their homes still stand as well.

• Read: John Caldwell and Sarah Dillingham Caldwell, his wife, Ipswich, Mass., 1654 : genealogical records of their descendants, eight generations, 1654-1900

Choate-Caldwell House, 16 Elm St. (Now at Smithsonian) - In 1963 this house was slated for destruction, but through the efforts of local preservationists was relocated to the Smithsonian where it resides as the Museum’s largest artifact on permanent display.

Eunice Stanwood Caldwell Cowles - Eunice Caldwell attended Ipswich Female Seminary from 1828 to 1829, where she began a lasting friendship with Mary Lyon. She married the Reverend John Phelps Cowles in 1838, and returned to Ipswich in 1844 to reopen the Seminary, which they ran until it closed in 1876.

Sarah Dillingham Caldwell - The story of Sarah Dillingham, wife of John Caldwell is of a loving and most thoughtful life.One of the first children born in Ipswich, and then orphaned, she became a "woman of qualities" that caused her name to never be forgotten. The years entrusted them with eight children and countless Ipswich descendants. Their home on High Street still stands.

Ipswich, Slavery and the Civil War - In 1765, Jenny Slew, a slave in Ipswich, successfully sued John Whipple Jr. for her freedom. In the mid-19th Century, the lines between ardent abolitionists, moderate anti-slavery people and those who avoided the discussion divided families, churches and the town of Ipswich.

33 High Street, the John and Sarah Dillingham Caldwell house (1660) - In 1654, Cornelius Waldo sold to John Caldwell for £26 the house and land he bought of Richard Betts. Caldwell removed the old house and built the present house with massive summer beams, a huge fireplace, a very substantial house of the 1660’s.

18 Green Street, the Isaac Stanwood – Joanna Caldwell House (1812) - Captain Isaac Stanwood was born in Ipswich, May 2, 1755. On January 24, 1775, he was enrolled among the Ipswich minute-men, and marched as a private in Captain Nathaniel Wade's company, in the alarm of April 19, 1775.

11 County Street, the Bennett – Caldwell house (1725) - Joseph Bennett built this early Second Period house in 1725. In 1818 the house was sold to Capt. Sylvanus Caldwell, who engaged in maritime trade along the coast from Massachusetts to Maine for a half century.

40 High Street, the William Caldwell House (1733) - William Caldwell built this house after purchasing the lot in 1733, The house remained in the Caldwell family into the 20th Century. Key features of the house include a large kitchen fireplace and exceptional period trim.

15 South Main Street, the Caldwell Block (1870) - The Caldwell Block stands on the site of the former Massachusetts Woolen Manufactory, constructed by Dr. John Manning in 1794. The property was sold to Stephen Coburn in 1847 and housed the post office and other shops. The building was destroyed by fire, and in 1870 Col. Luther Caldwell erected the present building.

25 County Street, the J. Caldwell house (c 1860) - The house at 25 County Street in Ipswich was built in approximately 1860 on a corner of the former Ipswich Jail grounds. The 1872 Ipswich map shows the owner as J. Caldwell. In 1910 the owner is N. S. Kimball. 

27 East Street, the Widow Elizabeth Caldwell house (1740-1755) - Joseph Wait sold this lot to Elizabeth Caldwell, widow of Thomas, in 1829. She moved a house from another site onto her property. The rear two story wing is believed to be the older house, joined together when the house was moved. Structural evidence suggest a construction dates of about 1740 to 1775 for the two sections.

Thomas and Elizabeth Lull, and the Caldwell sons - In 1714, Lydia Lull, the youngest daughter of Thomas and Elizabeth Lull, married William Caldwell, the third son of John Caldwell II and Sarah Foster to marry into the Lull Family. The wives of his brothers, John and Jacob, were her neices, being the daughters of Thomas Lull Jr. The homes of the two families were across from each other on High Street, and the 1660 home of John and Sarah Dillingham Caldwell still stands.

48 East St., the Tyler Caldwell house (1860) - Tyler Caldwell was "a man of thrift and industry, and amassed a comfortable property; respected in the town and well-beloved in the neighborhood where he lived."