Beginning at Morrissey Boulevard and Kosciuszko Circle at the northern extent of the Dorchester section of the city, it travels in a gently curving northeasterly direction 2.6 miles (4.2 km) through South Boston along beaches around the west and north shore of Dorchester Bay.

[2][3] It is owned and maintained by the Massachusetts Department of Conservation and Recreation as part of the Metropolitan Park System of Greater Boston.

[3] Day Boulevard was originally called the Strandway,[4] and was planned beginning in the late nineteenth century as the easternmost link of the Emerald Necklace, the string of connected parks and waterways created by Frederick Law Olmsted.

[5][6] Plans for the connection of Franklin Park across Dorchester via a parkway to be called Dorchesterway to South Boston and Marine Park at the east end of the South Boston peninsula via the Strandway were not realized, and the route was eventually called Columbia Road.

[10] Day Boulevard is listed on the National Register of Historic Places as part of the Old Harbor Reservation Parkways.