The part north of Roxbury Street in Dudley Square, Roxbury was laid out as a public way on January 19, 1662, and given its name May 9, 1825.

It ran from Dudley Square to the Rhode Island line and beyond to downtown Pawtucket.

It was named Shawmut Avenue, as an extension of that road from Dudley Square.

It is believed that, like many Irish musicians of his time, he played for dancers in the clubs around Dudley Square, Dorchester.

He started playing pickup chess on tabletops in Dudley Square, an African-American commercial district in Boston.

After the scandal, his trips to Dudley Square became all-nighters.

A large Irish population also developed, with many activities centered around Dudley Square, which just before and following annexation into Boston, became a central location for Roxbury commerce.

The Washington Street Elevated consisted of six stations, the most complex and major of which were at Dudley Square and Forest Hills.

For most of the twentieth century, Dudley Square was a multi-mode transportation hub, centered at Dudley Station of the Washington Street Elevated, which closed in 1987.

Two Silver Line services run between Dudley Square in Roxbury and downtown Boston along Washington Street in reserved bus lanes: