Established in at least the 13th century,[1] it runs for about 0.29 miles (0.47 km), from its junction with Market Street and Cheapside in the north to South Road (part of the A6), at Penny Street Bridge,[2] in the south.

[6] What was once the 1840-built Penny Street railway station became a nurses' home.

[7] The Church of St Thomas, in the southern section of the street, was built around 1840.

[1] 14 Penny Street dates to around 1785 and is now Grade II listed.

[8] The Brown Cow public house, at 42 and 44 Penny Street, is Grade II listed.