The city received complaints that, by the end of the century, the road's paving was broken up, there was a stench of pigsties in the area, and that the street was often blocked by loose pigs.

In 1497, St Margaret's Arch was built through part of the wall at the southern end of Bootham, providing access to what is now King's Manor.

[5][6] It continues the line of High Petergate, the via principalis of Roman Eboracum, from Bootham Bar in the York city walls.

[7] It runs north-west, over the York-Scarborough railway line, ending at a junction with Bootham Crescent and Queen Anne's Road, beyond which its route become Clifton.

On the north-east side lie most of the Georgian buildings: 15–17, The Exhibition pub, 25, 33, 39–45, 47 (designed by John Carr), 51, 53 and 55, 57, 59, 61, and 75–77 Bootham are all large houses, dating from the 18th century.

The main entrance to Bootham Park Hospital, built in 1777 as one of the first asylums in the UK, is up a long drive from the street.