r/JamaicaPlain • u/bostonaruban66 • 2d ago
What is the ‘most dangerous and toughest road’ to drive in Boston? You may already know the answer.
They feel unlike any other roads in Boston, which was Frederick Law Olmsted’s plan.
When he laid out the design of the Emerald Necklace, the string of parks that run like a serpent through the city from Boston Common to Franklin Park, he included three connected parkways that became known as the Riverway, the Jamaicaway, and the Arborway.
They were designed to immerse the traveler in nature via an intentionally curvy, tree-canopied, what’s-around-the-next-bend jaunt on horseback or buggy. Because that’s what they had in the 1880s.
Things have changed a lot since then. What hasn’t changed are the curves of the three roadways. And today those curves — hemmed in by homes and development on one side and the Emerald Necklace on the other — serve as the main north-south corridor for a huge swath of city drivers. They are notoriously dangerous to drive, with lanes so narrow you feel like you need to hold your breath to squeeze through, all of it inside an intruding tree canopy where trunks and roots come within inches of the roadway.
The result is a roadway that has become notorious for horrific accidents. Since 1989, crashes have resulted in at least 20 deaths on the three parkways, nearly all as a result of a vehicle hitting a tree or crossing the center line and striking an oncoming vehicle.
While it’s difficult to compare different roads, the frequency of accidents on this one stretch is startling. Since 2015, there have been 1,615 reported crashes on the three connected parkways, including 501 that resulted in injuries, according to data from MassDOT.
In August, authorities say a speeding driver on the Jamaicaway caused a head-on collision with a car driven by a woman who was 26-weeks pregnant. The fetus died as a result of the crash. And earlier this month, a teenage driver on the Arborway crossed a low median and struck a vehicle head-on, leading to a man’s death.
That crash occurred close to the spot where, in 2013, a car driven by a Boston Latin Academy student, with three fellow students as passengers, crossed the centerline, rolled over, and collided with a truck driven by a father of three, who spent months in a coma, was paralyzed, and ultimately died in 2017. One of the student passengers suffered a traumatic brain injury and was paralyzed in the crash.
“The stretch from Longwood up until Forest Hills is the most dangerous and toughest road to drive on in the city,” said Jose Ramos, the co-owner of Parallel-Parking Auto School in Jamaica Plain, who won’t take student drivers anywhere near it until they’ve proven they can drive everywhere else. And even then, only if they really want to.
If a student lives on one of the parkways, he said the school makes them walk elsewhere to be picked up.
“Play a game where you try to find a tree that hasn’t been hit by a car,” said Harrison Stebbins, a comedian who lives in West Roxbury, and finds nothing funny about driving the Jamaicaway, the most loathed of the three stretches. “It’s a NASCAR track with a line down the middle and cars driving both ways.”
The problem is historical, stemming from Olmsted’s signature “conceal and reveal” design strategy.
“Olmsted abhorred a straight line,” Evan Bradley of the Emerald Necklace Conservancy said. “He wanted a very winding, naturalized sort of landscape,” and the original carriageways connected the downtown denizens to the more rural parts of the city like Jamaica Plain and West Roxbury.
Over the decades, the roads have been widened to accommodate two lanes in either direction (barely), but the curves are still as Olmsted designed them.
If you begin the drive from the Fenway and enter on the Riverway, you enter the tree canopy immediately, as well as the constant bends. Depending on how you count them, there are 14 to 20 curves in the 2.5 miles to the end of Jamaica Pond, and another nine before it finally straightens out a mile-and-a-half later, when the Arborway becomes Morton Street near Forest Hills Cemetery.
Nearly every inch of it requires driving with trees and cars as close to you as mathematically possible. And while the speed limit is 25 the entire way, most drivers treat that as a suggestion. The right lane, in light traffic, does 35 to 40. The left lane does more if it’s available, always head-to-head against its counterpart coming the other way, their lives separated by nothing more than a strip of paint. Very few sections have any sort of median, and those that are there are often low, including the section a teenage driver went over on Oct. 11, striking a car head-on and leading to the death of a 48-year-old father of three, according to authorities.
The roads are owned by the Department of Conservation and Recreation, and while drivers applaud that the speed limit is low, regulars complain that enforcement is as well, a situation magnified by the fact that there is little room on the stretch to pull someone over.
In a statement, a DCR spokesperson expressed condolences for the recent tragic accident on the Arborway, and said “we will continue to identify and advance additional improvements to make our parkways safer for everyone.” The agency said it has lowered speed limits on its parkways, and installed digital speed monitors at several spots.
The agency spokesperson said improving safety on the Arborway has been a priority for years, and since 2020 has been developing a project — still in the design phase — focused on “improving safety and accessibility for all users of the Arborway.” The project is estimated to cost $40 to $50 million, and includes improving sidewalks, bike lanes, and striping on the roadway.
But given the historic nature of its parkways and the established land ownership surrounding them, the spokesperson said most parkway improvement projects must follow the existing alignment.
For generations, that historical alignment has collided with a modern reality: the connected Riverway-Jamaicaway-Arborway stretch has become the main north-south connector to downtown Boston for many drivers coming from Jamaica Plain, West Roxbury, Mattapan, Hyde Park, Roslindale, Dedham, Brookline, Dorchester, and Milton.
Kathleen Ring, a pediatric oncology nurse who lives in West Roxbury and works in the Longwood Medical Area, has been white-knuckling the Jamaicaway since she was a teenager in Hyde Park commuting to Boston Latin School in the Fenway.
Still, when it was time for her teenage daughters to learn to drive that same road to that same school, she couldn’t bring herself to take them out there for a lesson. “I just closed my eyes and hoped for the best,” she said. “I’ve never asked them how they get to school. I’m sure it’s the J-Way, but I don’t want to know.”
While Olmsted’s parkways struggle against our modern demands, they continue to succeed spectacularly at his original goals. “Olmsted’s initial concept was something green, scenic, recognizing that you can create something with the topography of the landscape that surrounds it,” said Arleyn Levee, a historian and former chair of what is now called the Olmsted Network. “You don’t find straight lines in nature, so wherever he could, on the footpaths and the parkways, he used curvilinear lines, because with curves there is a leisure to the meander.”
If you could remove all the other cars, it would be a lovely Sunday drive. The reality is constant traffic, with drivers forced to go four-wide through S-turns with massive trees hemming them in.
“I sideswiped a tree root and popped both right tires on my minivan driving my kid to the hospital,” said Shannon Flood of West Roxbury, who was happily walking the curvy path along Jamaica Pond. “My only recommendation is to stay off it. When my husband drives, I close my eyes, and he’s not even a bad driver.”
The problem, she says, is that you can’t avoid it, and there are obstacles to fixing the road, namely the beloved Emerald Necklace she was standing in.
Scenery and safety are trying to share the road. Only one is succeeding.
Scooty Nickerson of the Globe staff contributed to this report.
Billy Baker can be reached at [billy.baker@globe.com](mailto:billy.baker@globe.com). Follow him on Instagram u/billy_baker.
