The Jamaicaway was designed by Frederick Law Olmsted as part of Emerald Necklace of green spaces extending from Boston Common on Beacon Hill to Franklin Park in Roxbury.

Designed with carriages in mind during an era when Jamaica Plain was a sparsely inhabited streetcar suburb, the Jamaicaway is now a heavily-traveled route for motor vehicles connecting central areas of Boston (especially the Longwood Medical and Academic Area) with areas to the southwest, including Forest Hills, West Roxbury and the densely populated suburbs of Norfolk County.

The winding nature of the road, and its heavy use by commuters leads to many vehicle collisions.

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 American Mayor of Boston whose former house was long easy to spot, even after Curley's death, by the shamrock design incised in its shutters.