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 Lord’s 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. The Ross Tavern beside it was moved to Jeffreys Neck Road, where it is now known as the Wendell Estate.
Abutting the bridge on the west side was Bill’s Variety Store, which later became Immie Thayer’s bridal shop.
The photo below is the east side of South Main Street looking in the direction of the Old Town Hall, which is just out of the photo on the right. Note the electric poles, which indicate the photo was taken around 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)-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.
31 South Main Street, the Joseph Manning house (1727)-A house on this lot was purchased by Timothy Souther in 1794 and stayed in the Souther family until 1860. It was taken down in 1917, and the Dr. Joseph Manning house was moved to this location so that an automobile dealership could be constructed across from the Old Town Hall.
36 South Main St., the Hall – Haskell house (1820) Ipswich Visitor Center-ust past the Choate Bridge on South Main Street The Ipswich Visitor Center is located in the Hall - Haskell House, sometimes called the “Little Red House." Earlier structures stood at this site before mariner Charles Hall and his wife bought the property in 1819. In 1820 they built this house, where they lived upstairs and ran a general store on the lower floor.
37 South Main Street, Baker’s Store (b. 1828)-The first structure on the site was between 1692/3 and 1722. The former Baker's Clothing Store at 37 South Main Street was built in 1828 and has a combination of Italianate and Greek Revival elements.
54 South Main Street, the Ipswich Museum (1795)-This Federal-style structure was built in 1795 by John Heard, who became wealtthy as a privateer during the American Revolution. The house was purchased by the Ipswich Historical Society from the Heard family in 1939.
59 South Main Street, the Philomen Dean house (1716)-Dr. Philomen Dean bought this lot in 1715 and built a house. After various owners, the building was sold to the Boston and Ipswich Lace Co. in 1824, and an addition was built. In the late 19th century the building was used by as a tea room.
6 South Main Street, the Shoreborne Wilson – Samuel Appleton house (1685)-This house was built by joiner Sherborne Wilson,. The house was purchased in 1702 by Col. Samuel Appleton, the eldest son of Major Samuel Appleton. At the time it was still a two-room central chimney structure, and it is believed that Appleton expanded the building on the southeast side. The house is listed in the National Historic Register of Historic Places.
69 S. Main Street, the Samuel Dutch house (b 1733)-Samuel Dutch bought this land in 1723 and built this house by 1733. The front appears to have been enlarged with a third floor and a hip roof during in the early 19th Century. The rear wing has a chamfered summer beam, suggesting that it was an older house.