North Main Street starts up the hill directly across from Market Street, bears left at Meetinghouse Green and continues to an abrupt stop at the point where High Street and East Street merge. This neighborhood was once the religious, governmental and commercial center of Ipswich. During the seventeenth century, a meeting house, jail, fort, town pound and stocks were located here. Later the Post Office, Probate Court, Ipswich Female Seminary, Agawam Hotel and several commercial structures surrounded the Green. The most successful businessmen in Ipswich built fine Georgian, Federal, Greek Revival, Italianate and Victorian homes on North Main Street.
Boston was only three years old when the Governor and Council of the Massachusetts Bay Colony resolved to “hasten the planting of Agawam.” John Winthrop, Jr., the Governor’s brilliant, eldest son, led the expedition in March of, 1633. The first houses were “wigwams, huts, and hovels” built against the hillside near what is now the Town Wharf. Meetinghouse Green on Town Hill was the governmental center for early Ipswich. By order of the General Court, dwellings had to be within one half mile of the Meeting House at Meeting House Green. A meeting house was built here by 1636, surrounded by a high wall to protect them from the ever-present danger from Indian attacks. Several churches have stood at this same spot.
During the seventeenth century, a meeting house, jail, fort, town pound and stocks were located here. The town house and court was located near the present site of the Public Library, and lawyers stayed across the Green at the Treadwell Inn.Later the Post Office, Probate Court, Ipswich Female Seminary, Agawam Hotel and several commercial structures surrounded the Green.
The Meeting House Green District includes thirty houses, three churches and the town library which are sited around the steep, rocky Green itself and along Main Street. It encompasses a wide range of architectural styles with approximately half of the structures dating from the eighteenth century and half from the nineteenth.
12 North Main Street, Treadwell’s Inn (1737) - In 1737, Captain Nathaniel Treadwell opened an inn in this building. John Adams visited Ipswich frequently during the 1770's in his capacity as a lawyer and always stayed at Captain Nathaniel Treadwell's inn. It was erroneously named the Christian Wainwright house, which no longer stands.
16 North Main Street, the Stephen Coburn house (1845) - This Greek Revival home was built in 1845 by postmaster Stephen Coburn. After the death of his widow it became the Lucy B. Coburn Home for the Elderly, a benevolent institution, and is now Kaede Bed and Breakfast.
18 North Main Street, the Charles Kimball house (1834) - Charles Kimball attained honor as a colonel of the militia, a distinguished probate lawyer, and deacon of the Church. He was one of the original trustees of the Ipswich Female Seminary. The house shares a subdued Greek Revival style with the Stephen Coburn house next door. It is remembered as the home of the Manning School master.
19 North Main Street, Thomas Manning house (1799) - This house was built by Dr. Thomas Manning in January, 1799, and remained in the family until 1858, when it became a parsonage. This house is protected by a preservation agreement between the owners and the Ipswich Historical Commission. 
2 North Main Street, the John Appleton house (1707) - In 1962 the Appleton House was purchased by Exxon, which intended to build a gas station on the site. The Ipswich Heritage Trust was formed to save the house, the first major preservation action in Ipswich.
21 North Main Street, the Theodore Cogswell house (1880) - Abram D. Wait, et.al., sold this lot to Theodore F. Cogswell (953:203). Cogswell removed the 17th century house, once the “Black Horse Saloon” and built this Second Empire house at 21 North Main Street in Ipswich in 1880, with a fine Mansard roof. Cogswell was a grocer as well as clerk and treasurer of the Ipswich Savings Bank.
He also built the Victorian “painted lady” on North Main Street for his daughter and her husband after demolishing a first period home on that site.
22 North Main Street, the Colonial Building (1904) - The Colonial Building at 22 North Main Street was built in 1904 as a commercial attempt by the Feoffees of the Little Neck Trust. Ralph A. Daniels of Rowley had a furniture store in the building and Howard J. Blake, jr. had a hardware store at one time. One floor of the building was rented by the School Board in 1907 to accommodate the 9th grade. Charles Lampson converted the building into apartments about 1945.
25 North Main Street, the Ipswich Public Library - The Ipswich Public Library at 25 North Main Street in Ipswich is an 1869 Greek Revival building. The library and the first books were a gift to the town from Augustine Heard. and a large endowment by Professor Daniel Treadwell, whose family homestead originally sat at this location. The wings on either side were added later.
26 North Main Street, the Agawam House (1806) - Nathaniel Treadwell built the second Treadwell's Inn in 1806. In the mid-1800′s the inn was modernized with Victorian architectural elements and was renamed the Agawam House. It continued to be the town's first class hotel until it closed in the late 1920′s.
29 North Main Street, the Odd Fellows Building (1817) - In 1817 the Probate Court and Registry erected this building for its own use. In the year 1852, the Registry and its records were removed to Salem. By 1884 a second floor had been added, and it housed the Odd Fellows upstairs, with Blake's Drug Store downstairs.
31 North Main Street, the Methodist Church (1859) - The Methodist Society was established in Ipswich in 1824. The current Methodist Church on Meeting House Green was constructed in 1859. The steeple appears on the town’s seal, drawn by Ipswich artist Arthur Wesley Dow.
33 North Main Street, the Nathaniel Wait house (1865) - Nathaniel Wait was a cobbler, and placed on exhibit at the Essex County Fair a pair of fishing boots judged excellent for their absence of an inside seam. He was a trustee of the church and helped arrange the purchase of County land for construction of the present edifice in 1859.
34 North Main Street, the William Pulcifer house (1836) - William Pulcifer was a dry goods storekeeper who built the combination storefront, office and residence building at 34 North Main St. in 1836. This is the only brick residence in the Meetinghouse Green Historic District
36 North Main Street, the Dr. John Manning house (1769) - This house has one of the first preservation agreements in Ipswich, created by the Ipswich Heritage Trust. Dr. Manning was also an inventor and built an unsuccessful wind-driven woolen mill on the site of the present Caldwell Block next to the Choate Bridge. His second mill at the Willowdale Dam was more successful.
38 North Main Street, the Old Post Office (1763) - This structure was built in 1763 as part of the historic Dr. John Manning property. Probably originally a barn or warehouse, it became the post office in 1790. This building also served as the shop of Daniel Rogers, a master gold and silversmith who later moved to Newport RI.
40 North Main Street, the Captain Brewer house (1825) - Captain John Brewer bought two small parcels on North Main St. in 1824 and on them built the present house as a general store.
42 North Main Street, the John Johnson house (1871) - Margaret Kendall sold John A. Johnson this lot on Oct. 15, 1870. The old Fitts residence on the lot was moved to 43 High Street. Johnson built a large, elaborate Italianate mansion which remains one of the finest examples of that style in Ipswich. The gabled carriage house, complete with cupola and characteristic Italianate details, still remains. The Johnson shoe store was down the hill on Market Street.
44 North Main Street, the Harry K. Dodge house (1886) - Harry K. Dodge bought the homestead of the widow Margaret S. Kendall in 1886. He tore down the old house and erected this Victorian home.
45 North Main Street, the Isaac Flitchner house (1860) - In 1860 the Captain John Lord house was moved to Washington Street, and Dr. Isaac Flitchner built this fine Italianate house on the lot. It was the home of Justice Charles Augustus Sayward who tried the 18 defendants in the 1913 Ipswich Mills riot.
46 N. Main Street, the James Damon house (1866) - James Damon bought this property from Thomas Morley in 1866, removed an 18th century house and built this Italianate mansion. The 2 1/2 story house has Italianate window hoods, quoins, bracketed and decorated cornice, a bold arrowhead and dentil eaves. Damon was a businessman who owned the County Street Mill on Falls Island at Sawmill Point, as well as the “Damon Block” downtown in Ipswich. 
47 North Main Street, the George Farley House (1888) - In 1888 Theodore Cogswell bought the ancient Dodge house built in 1660 and tore it down to build this Victorian “Painted Lady” for his daughter Emiline and her husband George Farley, owner of the Farley and Daniels shoe company. Their son Theodore was a hero of WW I.
48 North Main Street, the Thomas Morley house (c 1750, alt. 1845) - This house and its northern neighbor, 50 North Main, were a single structure before 1845, when Thomas Morley bought the southern portion of that house, separated and rotated it 90° to present a gable end to the street, and finished it for his dwelling. Thomas Morley was an artist and taught painting in his school on Summer St., which stood behind the present 47 North Main.
49 North Main Street, the John Chapman house (1770) - This house was built in 1770 by John Chapman a "leather breeches maker." In 1822 Captain Ephraim Kendall sold the house to Ebenezer and Daniel Russell, and throughout the rest of the 19th Century the house stayed in the Russell family.
50 North Main Street, the James Brown house (1700 / 1721) - The James Brown house is part of a larger 1700 house that was divided into three houses in the late 18th Century. The chamfered oak frame in the southern portion indicates late First period, while the northern section appears to date from the 1720's. The Morley house next door was separated and turned sideways. 
51 North Main Street, the Sarah Lord house (1849) - Sarah Lord was the wife of A. P. Lord, whose general merchandise store existed at Lords Square for 100 years. Italianate motifs are featured in this house.
52 N. Main Street, the Treadwell – Hale house (1799) - This building is believed to have been built after the land was sold to Nathaniel Treadwell 3rd in 1799. He transferred to Joseph Hale one month later. There is a stone cooking hearth in the basement of the house, which is protected by a preservation agreement with the Ipswich Historical Commission.
56 N. Main St., the Dodge and Spiller Grocery (c 1850) - In 1854, Manning K. Dodge, who owned several lots at this end of North Main Street, sold the house to Richard K. Dodge. For several decades it was the location of the Dodge and Spiller grocery store.
57 North Main Street, the Day-Dodge House (1737) - This unusual double house has two entrances and asymmetrical bays. The corner at North Main and East Street is the oldest section and appears to have elements of a barn constructed by Francis Wainwright at this location in 1696. This house is protected by a preservation agreement.
58 North Main Street, the Captain Richard Rogers House (1728) - Captain Richard Rogers bought this lot in 1728 and built this high style, gambrel roofed house shortly thereafter. The balustrade, paneling and shell cupboards in this house indicate a high-style Georgian influence, one of the finest of its vintage in New England.
6-8 North Main St., Taverner Sparks (c.1671-1710) - The left side of this first period house was the home of taverner John Sparks and his wife Mary. The right side was added in the early 18th Century during ownership by the Smith family. Sparks' nearby hostelry was known far and wide, and Sessions of the Quarterly Courts met there for 20 years.
1 Meeting House Green, the First Congregational Church (1971) - A meeting house was built here by 1636. This is the sixth church on this spot. The previous historic building burned in 1965. This green has always been the religious and governmental heart of Ipswich.
12 Meeting House Green, the First Church Vestry (1832) - Built in 1832, the Vestry at 12 Meeting House Green was deeded to the First Church in Ipswich, Massachusetts in 1838 by George W. Heard, Esquire. It has served First church and the community of Ipswich as a Chapel and now as a coffee house and meeting place. The historic building was recently restored.
2 Meeting House Green, the Joseph N. Farley house (1842) - Joseph K. Farley, bought an old house on this lot in 1842, moved it to upper High Street, and built this "mansion.:The Ipswich Manufacturing Company opened in 1830, and Joseph Farley Jr. was the clerk and paymaster. His ambitious plan to divert water above the dam through a canal to supply power for a mill on the lower river near County Street never succeeded.
6 Meetinghouse Green, the Captain Israel Pulcifer house (1812) - On the night of June 9, 1811 the house on this lot burned with most of its contents. Captain Pulcifer rebuilt at once. Originally a hip-roof Federal style house, restoration in the 1870’s added a Second Empire mansard roof.
8 Meeting House Green, the David T. Kimball House (1808) - In 1808 the jail site was sold to Reverend David Tenny Kimball; the old jail was removed, and he built the house that is located there now. Rev. Kimball was highly respected for his ministry and a staunch abolitionist.
Meeting House Green Historic District - The North Green was once the religious, governmental and commercial center of Ipswich, and where the town's most successful businessmen built fine Georgian, Federal, Greek Revival, Italianate and Victorian homes.
