High Street runs parallel to Main Street, one block to the west, and carries almost all of Middletown's best domestic architecture. The street was developed in the early 19th century by merchants and professionals who wanted to be close to the commercial centre without living above a shop, and the resulting collection of Federal and Greek Revival houses is exceptional.
The Russell House at the northern end is the grandest, but the whole street from High and Court to the South Green is worth walking. Many of the houses have been converted to institutional or university use, which has kept them maintained without always keeping them visually accessible. The South Green at the southern end of High Street is one of Middletown's two public greens and has a more formal, civic character than the Main Street area.