Our first candidate:
The downramp in Charlesgate (right near the Fens) that leads down to Commonwealth Avenue.
I'm using this ramp pretty often this summer, whenever I need to get to Cambridge (I have a fun theatre gig at MIT) or Beacon Hill. I'm a big believer in avoiding biking on sidewalks as much as possible. And this sidewalk is very narrow and sometimes has people walking on it.
However, driving on the road presents a very difficult challenge, because on the right hand side of the ramp are a series of divots in the concrete that run perpendicular to the road, and are a couple inches deep.
This isn't the greatest photo, but they're deeper than they look, and there is a series of three, so you can't just hop over one, because if you try, you land on another one. They're deep enough and sharp enough to rattle your teeth, and certainly readjust (mal-adjust) several mechanisms on your bike.
For now the solution is either to try to survive them and hope not to pop a tire or crash into the cars next to me, drive in the lane (but this is impossible, because the cars drive way too fast down the ramp and don't leave any room), or ride on the sidewalk.
I'm not sure who is actually responsible for this road. I suspect it might actually be the state, rather than the city. If anyone has any good suggestions for who to call, please let me know. This is definitely hazardous spot, but one that's hard to avoid, because it helps me get across the Turnpike.
Here's where it is on the map, in case you're interested:
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