I had believed that Boston streets (within Boston proper) followed a naming convention by which streets changed name as they crossed over Washington Street, in honor of the first President. Summer becomes Winter, Essex becomes Boylston, and streets in the South End switch from East to West. My earlier entry on Washington Street states the naming convention to be fact. But an 1837 map shows Orange Street on both sides of Washington Street. This made me wonder--why didn't Orange Street change names? Then I started to wonder if the story I had always believed was in fact wrong. A quick research check shows that at least a few of the East/West streets in the South End appeared in 1868--Canton Street was layed out in 1826 but the names East and West Canton Streets are approved in April of 1868. Chances look good that the conventional wisdom is wrong.
Whatever the truth of the naming convention, if you ask anyone, and by anyone I mean anyone who can find their way around Boston, to name a street that doesn't change its name as it crosses Washington Street and almost all of them will have the same answer, "Mass Ave." For our out of town friends, Mass Ave appears on the maps as Massachusetts Avenue. But why does Mass Ave have the privilege of keeping its name as it crosses over Washington Street? Geography, as always, played a role.
When it was first layed out, Massachusetts Avenue looked like other South End streets, albeit with a confusing set of name changes over the years.
From the Annual Report of the Street Laying Out Department for the Year 1894 (Boston, 1895).
Chester Street, Boston, 1826; from Washington Street, west, 1826; named, September 15, 1834; extended from south-east side of Harrison Avenue to creek formerly the boundary line between Boston and Robuxry, with mall through the same, April 11, 1853; part of Chester Street incorrectly named Chester Square in 1857; Chester Street accepted, December 7, 1857; name of Chester Street from South Bay to Boston Water Power Company's land changed to Chester Park, June 22, 1858; name of East Chester Park, Chester Park. Chester Square, and West Chester Park changed to Massachusetts Avenue, March 1, 1894.
Chester Square, Boston, 1857; from Washington Street to Tremont Street; the part of Chester Street called Chester Square accepted, December 29th 1857; Chester Street named Chester Park, June 22 1858; "so much of the street now known in the records of the the City as Chester Park between Shawmut Avenue and Tremont Street" named Chester Square, Decmember 29, 1858 part of Chester park from Washington Street to Shawmut Avenue named Chester Square, March 3, 1864; Chester Square in cluded in West Chester Avenue, July 3 1869, part of West Chester Avenue from Tremont Street to Shawmut Avenue named Chester Square, October 5, 1869, part of West Chester Avenue from Washington Street to Shawmut Avenue named Chester Square, April 5, 1870; name of East Chester Park, Chester Park, Chester Square, and West Chester Park changed to Massachusetts Avenue, March 1, 1894.
Chester Park, Boston 1858, from Washington Street to Albany Street; from South Bay to Boston Water Power Company's land named Chester Oar, June 22, 1858; part east of Harrison Avenue named East Chester Park, November 16, 1858; from Shawmut Avenue to Tremont Street named Chester Square, December 29, 1858; called West Chester Park and so accepted, December 21, 1859l from Washington Street to Shawmut Avenue named Chester Square, March 3, 1864; from Washington Street to Albany Street named East Chester Park, April 27, 1869; East Chester Park named East Chester Avenue July 13, 1869 and East Chester Avenue named Chester Park, April 5, 1870; name of East Chester Park, Chester Park, Chester Square, and West Chester Park Changed to Massachusetts Avenue, March 1, 1894.
Got that straight? The key points are the date of the East/West naming (1868/1869) and the origin and termination points--the creek which used to run into Roxbury from South Bay (yes, South Bay, where the shopping center is, used to be water) marked one end of Chester Avenue and the Boston Water Power Company's land, which was part of the Back Bay landfill project (note the Chester Street name change in 1858, around the time the filling of the Back Bay began), marked the other. It was South Bay that determined the fate of Mass Ave--Chester Street was the first street which could be extended from Columbia Road to the Charles River with only a small bridge necessary to get over the tidal flats of South Bay. This 1890 map shows East Chester Street crossing over South Bay.
So why the sudden name change in 1894? My guess is that it is because the city created and/or renamed several major streets in Boston around this time because of continued work on Olmsted's metropolitan park system. In 1895, Columbia Road was created out of Columbia Street and a portion of Boston Street, then extended past the current intersection of Mass Ave, Boston Street, East Cottage, and West Cottage to link South Boston's parks to Franklin Park and, further on, the Jamaica Way. Because of its length and intersection with Columbia Road, East/West Chester Park/Street/Square must have seemed a logical choice for a prominent name like Massachusetts Avenue so the name could have been changed in preparation for connecting to Columbia Road. The Annual Report of the Street Laying Out Department for the Year 1894 shows the city paid $4320.00 for "land damages and toher claims, on account of laying out, widening, relocating, and extending streets" related to Columbia Street, the most paid for any street in the city.

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