Several hundred colonists sailed from England in 1630 in a fleet of 11 ships, including Winthrop's flagship, the Arbella.

The name they heard from Masconomet concerning the country over which he ruled has been reconstructed as Wonnesquamsauke, which the English rendered as "Agawam".

They also experienced their first nor'easter, which cost them some fingers and toes, as well as houses destroyed by the fires they kept burning day and night.

John the Younger resided with his father and stepmother until 1633, when he resolved to settle in Agawam, with the permission of the General Court of Massachusetts.

Captain John Smith had written about the Angoam or Aggawom region in 1614, calling it "an excellent habitation, being a good and safe harbour.

"[7] Nathaniel Ward, an assistant pastor in town from 1634 to 1636, wrote the first code of laws for Massachusetts and later published the religious/political work The Simple Cobbler of Aggawam in America[8] in England.

In 1638, Masconomet entered into a contract with John Winthrop the Younger for the purchase of Ipswich for "wampampeage, & other things: and ... also for the sume [sic] of twenty pounds.

"[9] There is no record of any Native resistance to the colonization either at Charlestown or at Agawam, though there is documentation of devastating virgin soil epidemics among indigenous people in the area around 1617 and again in 1633, and contemporary reports attest to ghost towns encountered by early English settlers.

The tidal Ipswich River provided water power for mills, and salt marshes supplied hay for livestock.

But in 1687, Ipswich residents, led by the Reverend John Wise, protested a tax imposed by the governor, Sir Edmund Andros.

Citizens were jailed, but then Andros was recalled to England in 1689, and the new British sovereigns, William III and Mary II, issued colonists another charter.

Ipswich Lace is a unique style, and the only known hand-made bobbin lace produced commercially in the U.S.[12] Great clipper ships of the 19th century bypassed Ipswich in favor of the deep-water seaports at Salem, Newburyport, Quincy, and Boston.

The town remained primarily a fishing and farming community, its residents living in older homes they could not afford to replace—leaving Ipswich with a considerable inventory of early architecture.

In 1822, a stocking manufacturing machine that had been smuggled out of England arrived at Ipswich, violating a British ban on exporting such technology, and the community developed as a mill town.

In the Ipswich witchcraft trial, a member of the Christian Science religion was accused of using his mental powers to harm others, including a spinster living in the town.

A grande allée, 160 feet (49 m) wide and lined with statuary, would run the half mile from house to sea.

In 1928, a new 59-room mansion designed by Chicago architect David Adler in the English Stuart style stood in its place, called the Great House.

At Mrs. Crane's death in 1949, the entire property was bequeathed to The Trustees of Reservations, which uses it as a venue for concerts and weddings.

In 2012 Ipswich hired its first female Town Manager, Robin Crosbie, who served until her retirement in 2018.

Much of the western end of town is dominated by Willowdale State Forest, and other parts of the town are also protected land, including Crane Wildlife Refuge on Castle Neck, the Parker River National Wildlife Refuge and Sandy Point State Reservation on Plum Island, Hamlin Reservation, Heartbreak Hill Reservation, Bull Brook Reservoir, Greenwood Farm, and part of Appleton Farms Sanctuary, which extends into Hamilton.

It is bordered by Rowley to the north, Boxford to the west, and Topsfield, Hamilton, Essex and Gloucester to the south.