Designed with carriages in mind during an era when Jamaica Plain was a sparsely-inhabited streetcar suburb, the Jamaicaway is now a well-traveled route for motor vehicles. Adding to the volume of traffic is the Jamaicaway's proximity to the Longwood Medical and Academic Area and to main roads leading to Forest Hills, West Roxbury and the densely populated suburbs of Norfolk County. The winding nature of the road, and its heavy use by commuters lead to many accidents, as evidenced by the damage done at vehicle height to many of the trees that line the Jamaicaway.
Curley house on the Jamaicaway
Many of the houses which line the Jamaicaway are large and of architectural interest. The oldest houses were created by elite Bostonians for year-round or seasonal use. The person most mentioned in association with the Jamaicaway today is probably James Michael Curley, the Irish AmericanMayor of Boston whose former house was long easy to spot, even after Curley's death, by the shamrock design incised in its shutters.