It is believed that Duncan Stewart was among the 9,000 Scottish prisoners taken in the "Battle of Dunbar" in 1650 by Oliver Cromwell during the civil war in England. Also, it is believed that he was selected to be sold into bondage in the New England states and, consequently, was settled in Ipswich, Massachusetts, as an indentured servant to a George Hadley. Here he met his future wife who was in service to George Hadley, possibly as an indentured servant also, but we assume by her own free will.

In 1659, the couple moved to Newbury, MA, where they resided for 30 years on a farm on that part of the Dummer estate which became a portion of the Caldwell farm in the Byfield Parish and near the Rowley line.

In 1690, they moved to Rowley where Duncan is on the tax list of 1691 when he was assessed 2 pounds. By deed, dated 20 February 1698/9, "Dunckin Steward of Rowley, planter" sold to Capt. Stephen Greenleaf of Newbury, MA, the rate lot and right in undivided lands in Newbury, MA, belonging to "his son Charles Steward, late of Newbury, deceased." Essex Deeds, 16:17.

Duncan Stewart was among those "inhabitants of Rowley living northwest of Rye Plain bridge and Long Hill," 16 March 1702/3, whose minister's rates were abated.

On 17 March 1713/4, four sons of Duncan Stewart signed an agreement for the maintenance of "their aged and honored parents, Duncan and Ann Stewart" who had resided with their son, John, since 1707. Ann Stewart, "tho't to be nearer a 100 yⁿ 90 years" was admitted to the Rowley church on 17 September 1721.

"No evidence whatever has been found to show that Duncan Stewart or any of his sons ever engaged in shipbuilding or owned a shipyard, as stated in Gage's History of Rowley, p. 318." G. B. Blodgette and Amos Jewett, "Early Settlers of Rowley, Massachusetts," p. 356.

Duncan and his wife Ann (Winchurst) Stewart had twelve children, the first two born in Ipswich, MA, the others born in Newbury, MA:

• Jane, m. 2 June 1682 Joseph Esty of Topsfield, MA.
• Kathren (Catherine), b. 8 June 1658; m. Paul Wentworth.
• Martha, b. 4 April 1659; m. John Wentworth.
• Charles, b. 5 June 1661; d. 8 May 1689; unmarried. In Nov., 1688, he was "impressed" to serve in a winter's campaign against the Eastern Indians. Coffin's History of Newbury, p. 151.
• Elizabeth, m. 2 Nov. 1662 Sylvanus Wentworth.
• James, b. 8 Oct. 1664; m. Elizabeth -----.
• John, b. ca. 1666; m. Elizabeth -----.
• Anna, m. Colin Frazer.
• Henry, b. 1 May 1668; probably died young.
• Solomon, was a member of Capt. Philip Nelson's Company in the Canada Expedition of 1690, and died of starvation on board teh brigatine Adventure, William Bedlow, master, in December 1690. Massachusetts Archives, 37:48.
• Samuel, m. Dorcas Boston. Lived in Wells, ME.
• Ebenezer, b. ca. 1676; m. Elizabeth Johnson.