Thomas Franklin Waters wrote in Ipswich in the Massachusetts Bay Colony that in past times High Street was also called Hill Street, Great Street, Broad Street, Long Street, Bay Road, and The King’s Highway. The section beyond the Old North Burial Ground was “the West End,” a tradition long forgotten, but going in the other direction High Street abruptly changes its name to East Street, and that neighborhood is still known as “the East End .”

A 1910 view of High Street looking north from Mineral Street. Asa Lord’s Store and Burnham’s Grocery in the middle of the photo at Lords Square are gone, but most of the other houses in this photo are still standing.

High Street dates back to the founding of Ipswich in 1633. It was the main residential and commercial street of the new community. The predominant character of the street is now residential, but several of the 17th, 18th, and 19th Century houses along High Street earlier served as taverns, stores, or craftsman’s shops.  Ipswich was an important stop on the Old Bay Road, which incorporated High Street, and by 1828, up to twelve stages were passing through town daily, with an overnight stagecoach stop in Ipswich established by 1761. Central Street was built in 1871 and much of the High Street traffic was redirected. The High Street Historical District in Ipswich was added to the National Register of Historic Places in 1980.

First Period houses on High Street
This colorized photo from the late 1800’s was taken from the intersection with North Main Street. The John Gaines house is on the right. Elm trees graced High Street and there were no electrical lines.
High Street in 1859, looking toward North Main Street.
The Stone-Rust house is on the left in this photo from the early 1900's, provided by
The Stone-Rust house is on the left in this photo from the early 1900’s.
The old straw-roofed Baker house that once stood on High Street
The old straw-roofed Baker house that once stood on High Street
A small rise in High Street was removed in the 19th Century.
A small rise in High Street was removed in the 19th Century. This photo is taken looking toward North Main Street. On the fight front is the Caldwell house. On the left front is the Lord-Baker house.
High Street looking in the opposite direction, with Lord’s Square at the end
High Street in Ipswich MA, 1900
High Street from the top of North Main Street
Burnham's Store on High Street at Lord Square
Burnham’s Store on High Street at Lord Square
The corner of Manning nd High Street
The corner of Manning and High Street. The houses on the left and in the center no longer stand.
High Street before the bridge was built, with Town Farm Road on the right.
The High Street railroad crossing before the bridge was built
High St. bridge, newly constructed
High St. bridge, newly constructed
Memorial Day parade on High Street just above Lord Square
Memorial Day parade on High Street just above Lord Square

 Houses in the High Street Historic District:

Address Historic name of house Year Built Post
1 High St Rogers Old Manse 1727 Read
3 High St John Gaines 1725 Read
4 High St Pink House 1850
6 High St Whittier Funeral Home 1890 Read
7 Hgh St non-historic house 1960
8 High St Frederick Ross 1887
9 – 11 High St Samuel Newman 1762 Read
10 High St non-historic house 1927
12 High St William Russell 1890 Read
13 High St Joseph Willcomb 1668 Read
14 High St George A Lord 1857
16 High St Jacob Manning 1818 Read
17 High St Thomas Lord 1658 Read
21 High St Haskell-Lord 1750 Read
23 High St. Unnamed 1870
24 High St J.W. Gould 1810
25 High St View 1870
26 High St Phillip Call 1659 Read
27 High St Edward Brown 1650 Read
29 High St Harris House 1819
30 High St Joseph Bolles 1720 Read
33 High St Waldo-Caldwell 1660 Read
34 High St White Horse Inn 1658 Read
36 High St unnamed 1890
37 High St Lord-Baker 1720 Read
38 High St unnamed 1875
40 High St William Caldwell 1733 Read
41 High St Daniel Lummus 1686 Read
42 High St Holland-Ringe 1742 Read
43 High St James Fitts 1767
44 High St Ringe-Newman 1780 Read
45 High St Jonathan Lummus 1686 Read
48 High St unnamed 1860
53 High St unnamed 1870
54 High St Kingsbury-Lord 1660 Read
55 High St unnamed 1863
56 High St unnamed 1860
57 High St Stone-Rust 1750 Read
58 High St unnamed 1870
60 High St unnamed 1870
61 High St View 1700
66 High St Harris – Jewett 1795 Read
68 High St Wood-Lord 1725 Read
71 High St View 1750
73 High St Nathaniel Lord 1720 Read
77 High St John Kimball 1680 Read
79 High St View 1814
82 High St Brewer – Bowles 1700 Read
83 High St Old Jail 1771 Read
84 High unnamed 1830
85 High St Eliz/Phillip Lord 1774 Read
87 High St Sewall P. Jewett 1830
88-92 High St Simon-Shatswell 1690 Read
89 High St Jewett-Cole 1780
91 High St unnamed 1870
93 High St John Cole – Jewett 1813
94 High St unnamed 1870
95 High St Simon Adams 1700 Read
96 High St View 1870
98 High St Unnamed 1860
100 High St Joseph Fowler 1756 Read
102 High St unnamed 1870
103 High St Merchant-Choate 1639 Read
104 High St John Kimball 1715 Read
106 High St Orange Shutters 1715 Read
108 High St Dow-Harris 1735
110 High St John Kimball Jr. 1730 Read
112 High St View 1770
114 High St Tibets-Fowler 1860
115 High St Baker-Sutton 1725 Read
118 High St Aaron Rutherford 1860  

The Legend of Puddin’ Street

For the 250th celebration of the founding of Ipswich, the Rev. Knowles wrote a poem which noted the unusual names of Ipswich streets. There is a very old legend about some mischievous boys who stole a bag pudding and kicked it down the road, lending High Street its most colorful nickname, “Puddin’ Street.”

We turn our eyes below and at our feet
Lies in peace old Pudding Street
So named because a pudding hard and dry
Was stolen by some tipsy passers by
These later years from vulgar names have shrunk
And called it High because the thieves were drunk

Cooking a pudding in a bag
Another version of the story is memorialized in a poem written by Henry Bowen long ago:

I can remember very well
A tale the old folks used to tell
Of how a street well known to fame
Received its somewhat curious name
The oven then so long ago
Was built outside the house and so
While the good wife was getting dinner
There came along a tramping sinner
Who having not the fear of man
Opened the oven door and ran
The pudding had so much of heat
He quickly dropped it in the street
And fearing in that place to stay
Kicked it before him on his way
The pudding bag so stout at first
By violence at last was burst
And ever since that wicked feat
The thoroughfare is Pudding Street

Ipswich Village on the Old Rowley Road

Ipswich Village Philander map 1832
High Street continues north through a neighborhood beyond the Clam Box known as Ipswich Village, until it reaches Rowley. Thomas Franklin Waters wrote in 1915, “At the very beginning of the Town, High Street was the road to Newbury or ‘the pathway leading toward the River of Merrimac.’ No section of our Town has more substantial and picturesque interest than this quiet neighborhood.”  Image: Ipswich Village, from the 1832 Philander map of Ipswich. Continue reading…

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