No. 21941 Detail from 1889 atlas showing the route from Edward Everett Square (indicated by red circle) to Pond Street to Crescent Avenue. Note that Boston Street extends north and south of the intersection.
No. 21942 Detail from 1894 atlas showing the route of the new Columbia Road Parkway leading east from Edward Everett Square on a new tour somewhat north of Crescent Avenue.
In the nineteenth century, the stretch of Columbia Road from Edward Everett Square to Uphams Corner was part of Boston Street. Columbia Street extended from Uphams Corner to Blue Hill Avenue. Pond Street ran from Edward Everett Square eastward, making a jog, then leading to Crescent Avenue. In the late 1890s, Columbia Road was created by improving Columbia Street and, a portion of Boston Street and creating and new straighter road from Edward Everett Square eastward to and across Dorchester Avenue .
Frederick Law Olmsted envisioned the Dorchesterway as the final link in his Emerald Necklace. Te “necklace” runs from Boston Common out to Arnold Arboreturm, then turns and runs bia the Arborway to Franklin Park. The Dorchesterway was meant to extend the roads to connect to the Strandway (Day Boulevard) running to South Boston’s Marine Park and Pleasure Bay. These grand thoroughfares would connect the natural-looking green spaces Olmsted designed for Boston.
The following is from The Boston Globe, April 30, 1900
One might begin at the Commonwealth Av end of this chain and, a few years hence, when the parks and boulevards are competed, a drive can be taken as follows: Through the Back Bay fens, along the Riverway, through Leverett Park, Jamaica Park, Arborway, Fraanklin Park and then on to what is known as the Marine Park system, which includes Dorchesterway and Strandway to the Marine Part itself, which is the further end of the chain.