I don't know where this is coming from; I've been in MA for a long time and never any road obstacles like the above. Now having said that driving backroads is not easy to do fast simply because they are windy and narrow.
I guess if you compare to someplace like Arizona where if you spin out you just end up in sand instead of hitting a tree, sure, but why single out MA instead of just anyplace with trees? :)
I am not kidding about this: there are places in the Midwest where people have been required to remove trees from their front yards in order to make things safer for drivers who might drift off roads.
My grandmother lived o a very wide but otherwise normal street in South Bend, IN. She had a row of GIANT oaks in front of her house. There were at least 3 crashes I heard about that killed drivers. People would drive down the street way too fast, hit a slight bump about 40-50 feet down the street from her house and lose control. The city offered to cut down the trees after 4 teenagers died a while back. She declined though, because they would end up in her living room if they didn't hit the tree.
That being said, there's only one tree left, cause that last accident killed the tree they hit.
I'm from Minnesota and have put in 100,000+ miles of driving there, much of it in the winter. I'm not sure how I feel about removing trees and other side-of-the-road obstacles, but just wanted to point out that it's possible in very bad conditions to drift off the road, spin out on the highway, rear-end the car ahead, etc. even if you're being extremely cautious. I hit black ice at 30 mph on the highway and my car rotated a full 540 degrees, but fortunately didn't end up in a ditch. Sometimes conditions and visibility can be so bad in Minnesota, that I don't think any outsider can understand how difficult it is just to stay on the road. I've taken drives where you see cars in the ditch every quarter mile. I rear-ended a guy once, but he wasn't even angry because he saw my car slide slowly toward him from at least 50 feet away.
I understand the need for life to go on in places with hostile weather, and also that unexpected situations come up.
But at some point, a reasonable standard must be set, and if you can't drive safely you shouldn't be driving. Clearing obstructions on the side of the road won't really help if you're spinning out of control on a busy highway.
In greater Boston, the DCR (Department of Conservation and Recreation, formerly the MDC) maintains many arterial roads such as Storrow Drive, Memorial Drive, VFW Parkway, the Jamaicaway/Arborway, etc.
These roads are considered "pleasure roads" and date back to the day when a drive in the outdoors was primarily recreational. The roads connect and traverse major parklands.
DCR is not part of MassDOT (Department of Transportation). These roads are not necessarily built to traditional highway standards.
For example, trees along Memorial Drive and the Jamaicaway are closer to the roadway than would generally be recommended. These characteristics are linked to the historic character of these roads and their surrounds. Periodically, there will be plans to change the roads in some way, but they are usually met with significant pushback (neighbors, parks people, preservationists). On the other hand, the DCR for years resisted standard pedestrian crossings as well.
Currently, I think there is a slow trend to make these roads more standard where possible but also slow traffic speeds and improve pedestrian access.
I'm assuming you haven't had much chance to compare, so I'll give you my impression (having driven rural roads in CA, NV, NM,UT,CO, AZ, KS, MO, IL,TN,PA, and every East coast state except FL in the past six months.) RI, CT, and MA are very uncomfortable because it's common to have narrow roads with rocks and trees no more than 18 inches off the roadway. In VA, for a contrast, trees grow everywhere, but along rural highways there is only relatively short grass for the first 15 or so feet off each side. And everyone who drives VA enough hates the state for its police (which I've heard frequently from people living in every state from new York to south Carolina.) There are also places in VA where that dynamic doesn't exist (west of the Appalachian trail) because, like you said, the winding roads, rather than police, do the job of slowing cars down.
And admittedly AZ is easy. Passing in the oncoming lane while going 90 is a pretty comfortable thing there.
I guess if you compare to someplace like Arizona where if you spin out you just end up in sand instead of hitting a tree, sure, but why single out MA instead of just anyplace with trees? :)