The Jamaicaway (also known as The Jamaicaway) is a four-lane, undivided parkway in the Jamaica Plain neighborhood of Boston, Massachusetts near the border of Brookline.

The Jamaicaway was designed by Frederick Law Olmsted as part of a series of parks and parkways extending from downtown Boston to Franklin Park in Roxbury. The Jamaicaway connects the Riverway in the north with the Arborway in the south.

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 evinced by the damage done at vehicle height to many of the old trees that line each side of 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 American Mayor of Boston whose former house is easy to spot by the shamrock design incised in its shutters.

References

Sources

• Arnold Arboretum
• Frederick Law Olmsted National Historic Site
• The Emerald Necklace Conservancy