It encompasses the oldest section of High Street, which was laid out when Ipswich was founded in 1633.

The district runs for four blocks from the junction with Town Farm Road and the railroad right-of-way in the west, to North Main Street in the east.

[2] Ipswich was from its earliest days an important transit stop, and High Street was the location of its inns for travelers.

In the 18th century small industrial shops also populated the street, and some of these led to the building of larger textile firms elsewhere.

[2] The district contains more than thirty structures built before 1750, many of which retain First Period and Georgian styling.