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

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. Jamaicaway connects Riverway in the north with Arborway in the south.

Designed with carriages in mind during an era when Jamaica Plain was a sparsely inhabited streetcar suburb, 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.

Many of the houses which line 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 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.

The entire route is in Boston, Suffolk County.

Location	mi	km	Destinations	Notes
Jamaica Plain	0.0	0.0	Pond Street / Francis Parkman Drive / Arborway south – Dedham, Providence	Traffic circle; northern terminus of Arborway
Mission Hill	1.5	2.4	Route 9 / Riverway north – Copley Square, Brookline	Interchange; southern terminus of Riverway
1.000 mi = 1.609 km; 1.000 km = 0.621 mi

• Restoring Boston’s "Emerald Isles"
• Frederick Law Olmsted National Historic Site
• The Emerald Necklace Conservancy
• "2 Killed in Early Morning Jamaicaway Crash" - October 19, 2014 - Boston Globe