In March 1692 several Ipswich persons petitioned “to have liberty granted them to build shops upon ye bank by ye river side,” at what is now South Main Street. The Selectmen laid out this stretch of land in twenty-three small lots and granted them “to as many individuals with the conditions that they not encumber the highway, make provision for drainage under the buildings, that each person provide paving four-foot wide all along before ye said buildings for the convenience of foot travelers, and erect posts to keep horses from spoiling the same.” It was stipulated by the Town that the lots extend no farther into the river than “ye low water mark.” South Main Street in Ipswich was devastated by America’s love of the automobile. In the 20th Century, beautiful old houses here and at the other end of town on Lords Square were demolished and replaced by garages and service stations.
The Ross Tavern abutted the Choate Bridge on the downstream side. It was built in 1690 in downtown Ipswich, but in 1735 it was moved to the south-east side of the Choate Bridge where it remained until 1940 when it was disassembled and moved to its present location on Jeffreys Neck Road at the former Wendel Estate, where the original timber frame was restored and reassembled. 17th Century fireplaces and 17th & 18th century woodwork are features inside the house.
The Sherborne Wilson House built in 1685 till stands near the Choate Bridge. It was later the home of Samuel Appleton, descendant of the early settler. The Ross Tavern beside it was moved to Jeffreys Neck Road, where it is now known as the Wendell Estate.
The photo below is the east side of South Main Street. The electric poles indicate the photo was taken after the turn of the 20th Century. Of the houses shown here, only the Sherborne Wilson house, the corner of which is in on the left, still stands. The building on the far right with the Mansard roof was the Ipswich Savings Bank at the corner of South Main Street and Elm Street, and the bell tower on the Old Town Hall can be seen above and beyond that house. The second photo is the same view as seen today. The Birds Eye map of Ipswich below confirms Bill Varrell’s description in Images of Ipswich.
15 South Main Street, the Caldwell Block (1870)
30 South Main Street, the Old Town Hall (1833)
31 South Main Street, the Dr. Joseph Manning house (1727)
36 South Main St., the Hall-Haskell House (Ipswich Visitor Center), 1820
37 South Main Street, Baker’s Store (b. 1828)
41-47 South Main St., R. W. Davis dealership (1930)
54 S. Main St., the Heard House / Ipswich Museum
57 South Main Street, Ipswich Mills boarding house (1876)
59 South Main Street, the Philomen Dean house (Old Lace Factory) (1716)
6 South Main Street, the Shoreborne Wilson – Samuel Appleton house (1685)
69 S. Main Street, the Samuel Dutch house (1733, rear section may be older)
Historic Ipswich 