It's not rough. At night it has some sketchballs and when the clubs get out there's more raucous stuff but I wouldn't worry about walking through there at that hour. Just be smart aware.

During covid it was the sketchiest I ever remember it being though.

It's actually one of the few areas of Boston that I would say is a bit sketchy at 2am.

Not the best area, but use common sense and stay alert and you would probably be fine.

Let’s just say that I would never park my car here

It’s pretty rough in the sense that there are homeless addicts, but people usually don’t bother you unless you bother them. I walked those streets to the T at night alone as a female student for years and never had an issue. I did carry pepper spray on me, but never had to use it. Just be smart and aware of your surroundings. There is also no parking on Winter Street, not even street parking, so I assume you would be parking on Tremont or elsewhere. Just FYI

At that time it's typically homeless people sleeping. But not dangerous, I walk from my apt to planet fitness all the time around midnight

I don't think there has been a time in the last 2 years where I wasn't accosted in some way in that area, I've probably been there like 10-15 times in that timeframe.

Lot of homeless people, you’ll probably just be asked for spare change a bunch, at least in my experience. I’d say it’s sketchy but generally safe.

Yeah, I guess it depends. I worked in that area for five years from 2018-2023 and the worst that’s happened to me on that street was being cat-called. Boston Police are usually monitoring all over that area, too. Just be smart and you shouldn’t have any problems.

Define accosted? Being asked for spare change to being followed and threatened is a continuum.

I wouldn't worry so much about walking but parking my car? Higher chance than most of Boston it may get broken into.

Lol park where? There's not a bevvy of street parking. I wouldn't worry about my car Ina garage.