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I've lived in Boston for 7 years, and medium-sized cities in CT for the rest of my life. I can say without a doubt that I felt much safer living in Boston than I have living in CT. While I wouldn't think twice about walking across Boston late at night/early in the morning, I wouldn't think to do the same thing in my current town in CT, or where I grew up. It isn't a matter of age - I've stayed overnight in Boston a few times since I moved back to CT, and I haven't adjusted my late night habits in those instances.
It's not a matter of the CT cities being unsafe; neither city has a high crime rate, and they're relatively quiet places. It's just my own comfort level.
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