A stretch of three interconnected parkways in Boston has gained a reputation as one of the region’s most dangerous roadways, with a history marked by frequent and often fatal crashes. Since 1989, there have been at least 20 deaths linked to accidents on these roads, primarily caused by vehicles striking trees or crossing into oncoming traffic.
The parkways — Riverway, Jamaicaway, and Arborway — are known for their narrow lanes, sharp curves, and proximity to large trees lining the edges. According to data from the Massachusetts Department of Transportation (MassDOT), 1,615 crashes were reported on these parkways between 2015 and 2026, including 501 resulting in injuries. Drivers regularly exceed the 25 mph speed limit, often traveling at 35 to 40 mph or more, despite the risks.
Tragic incidents continue to underscore the dangers. In August, a speeding driver on the Jamaicaway caused a head-on collision resulting in the death of a fetus, after crashing into the car of a woman who was 26 weeks pregnant. Earlier in October, a teenage driver on the Arborway crossed a median and collided with another vehicle, killing a 48-year-old man. This location is near the scene of a 2013 crash that involved Boston Latin Academy students, which left a truck driver paralyzed and later deceased, and injured students suffering serious long-term disabilities.
Local driving instructors and residents describe the section between Longwood and Forest Hills as the most challenging and hazardous in the city. Jose Ramos, co-owner of a driving school in Jamaica Plain, avoids teaching students on these parkways until they have gained experience elsewhere. “If a student lives on one of the parkways, we make them walk to be picked up,” Ramos said, referring to safety concerns.
The roads’ historical design plays a key role in the difficulties drivers face. Frederick Law Olmsted, the landscape architect behind Boston’s Emerald Necklace, originally designed the parkways with naturalistic, winding curves intended to reveal scenery gradually and discourage straight-line travel. Over time, the roadways were expanded to accommodate two lanes in each direction, but the original curvilinear layout and the restrictive tree canopy have largely remained intact.
The close proximity of trees to the roadway leaves little room for error. Many sections lack medians, and where medians exist, they are often low and insufficient to prevent vehicles from crossing into opposing lanes. Officials responsible for the roads, managed by the Department of Conservation and Recreation, acknowledge the challenges of balancing safety with preservation. Enforcement of speed limits is reported to be inconsistent despite widespread community concerns, and the parkways serve as key connectors for commuters from multiple Boston neighborhoods and suburbs.
Residents express mixed feelings about the parkways. While many appreciate the historical and scenic value, the risks for daily commuters are a source of anxiety. Kathleen Ring, a nurse and longtime commuter on the Jamaicaway, recalled her own fears driving the route and said she avoided supervising her teenage daughters driving there. Others describe the roads as resembling a race track, with dangerous head-to-head traffic and little margin for error.
Experts and advocates emphasize the tension between maintaining Olmsted’s vision of natural beauty and the realities of modern transportation demands. Historian Arleyn Levee noted that the curved design creates a leisurely drive when traffic is light and the roads are free of other vehicles. However, the combination of heavy traffic, speeding, and limited physical space for safety features has created a landscape where scenic appeal and driver safety often conflict.
Efforts to improve safety face constraints due to the protected status of the Emerald Necklace parkways and the need to preserve the historic environment. Meanwhile, drivers are urged to exercise caution, though some say the best advice is to avoid these roads when possible.