South Main Street postcard, Ipswich MARoads

South Main Street

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.

South main St. Ipswich MA

This photo of South Main Street and the mill was taken from the roof of the Ipswich Female Seminary.


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 Ross Tavern on South Main St. Photo is from the late 1800’s

By the time the Ross Tavern was moved in the 1940’s it was in sad condition. Behind it is the building that antiques dealer Ralph Burnham put together from several small buildings, which later became “The King’s Rook”.

Set back a bit from where the Ross Tavern stood, Ralph Burnham assembled several old buildings into one building which he intended to use as an art gallery. It later became a music venue known as the Kings Rook and the Stonehenge Club. and finally as a restaurant before it was torn down and replaced by the similar-looking professional building at that location now.

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.


Abutting the bridge on the west side was Bill’s Variety Store, which later became Immie Thayer’s bridal shop. It burned after the Mothers Day flood of 2006.

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.


Bill Varrell wrote in Images of Ipswich, “Baker’s Express wagon is parked on the west side of South Main Street in front of Baker’s Clothing Store (now Fiske and Freeman antiques). To the right of the photograph are several early houses, now destroyed or moved. The Old Town Hall is out of the photo but the bell tower that once graced its roof can be seen above the house with the Mansard roof.

This is a photograph taken recently from the same location. To the left of the Old Town Hall is the 1847 building that is home to JoAnne's Florist. It would be hidden behind other buildings in the old photo.

This is a photograph taken recently from the same location. To the left of the Old Town Hall is the 1847 building that is home to JoAnn’s Florist. It would be hidden behind other buildings in the old photo.




South Main Street in the 1893 Birds Eye Map of Ipswich. The Choate Bridge is on the left, and the Old Town Hall is on the right. The west side of South Main Street was lined with houses as well, some of which survive, but several of which were demolished to build the town’s first auto store and garage, formerly the home of Jungle Printing.


The intersection of South Main and Elm Streets. The Ipswich Savings Bank was on the right. In the distance is the Choate Bridge, a line of small shops at the foot of North Main St., and the Ipswich Female Seminary behind them. Photo provided by Bob Swan.

A view of the rear of the buildings on South Main Street, just below the dam was known as

A view of the rear of the buildings on South Main Street, just below the dam was known as “Little Venice.” Photo by George Dexter, circa 1890.

South Main Street, looking from the other direction. Several of these houses still stand on South Main, including the Philomen Dean House (Old Lace Factory) in the foreground. In the distance is the approach to the Choate Bridge.


This photo was provided by Eric Van Horn. Imagine these unpaved streets after it rains!


Auto dealer (and former bicycle mechanic) Ernest Currier built a garage to service Model T’s at this location. He removed the buildings in the center and on the left, and moved the Dr. Manning house on the right closer to the Choate Bridge, where it still stands.

R. W. Davis, Ipswich MA

R. W. Davis automotive dealership, S. Main St. Ipswich MA

Some buildings on South Main near the Choate Bridge were spared demolition.


The same view of South Main St. today


Click on the image to use a slider that juxtaposes the old and new image of South Main Street.

The Caldwell Building Choate Bridge Pub 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.
30 South Main Street, the Old Town Hall (1833) - The Unitarians built their church here in 1833 but sold it to the town ten years later to be used as town hall. The lower section was constructed at the corner, the old Unitarian Church was moved on top.
Josephy Manning house, South Main Street, Ipswich 31 South Main Street, the Dr. 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 (Ipswich Visitor Center), 1820 - The Ipswich Visitor Center is located in the Hall-Haskell House on South Main Sreet.. Open weekends in May, seven days a week Memorial Day through October.
37 South Main St., Ipswich MA 37 South Main Street, Baker’s Store (b. 1828) - The former Baker's Clothing Store at 37 South Main Street was built in 1828. Properties along the river side of South Main St. were granted in the late 17th Century to establish businesses along the corridor where people entered the Ipswich.
R. W. Davis automotive dealership, S. Main St. Ipswich MA 41-47 South Main St., R. W. Davis dealership (1930) - The buildings at 41 and 47 South Main were the R. W. Davis automotive dealership. By 1930 the Thomas Manning house had been moved to the Timothy Souther lot, and R. W. Davis had built a brick building for his automobile dealership. The buildings currently house Anntiques.
54 S. Main St., the Heard House / Ipswich Museum - The Museum provides tours of the First Period Whipple House and works by nineteenth-century Ipswich Painters including Arthur Wesley Dow.
57 South Main Street, Ipswich Mills boarding house (1876) 57 South Main Street, Ipswich Mills boarding house (1876) - The building at 57 South Main Street was erected by the Ipswich Mills Corporation for use as a boarding house. In the early 20th Century, Madeline Linehan operated the Ipswich Mills Tea House in the building.
59 South Main Street, the Philomen Dean house (Old Lace Factory) (1716) 59 South Main Street, the Philomen Dean house / Old Lace Factory (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 for the machinery.
6 South Main Street, the Shoreborne Wilson – Samuel Appleton house (1685) 6 South Main Street, the Shoreborne Wilson – Samuel Appleton house (1685) - 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.
Samuel Dutch house, S.Main St., Ipswich MA 69 S. Main Street, the Samuel Dutch house (1733, rear section may be older) - 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.

Categories: Roads

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