I've lived in 4 places: Ottawa (Canada); Portland, Oregon; Santa Clara, California (SF Bay Area); and now Hanover. My ranking for favorite places to live:
1) Hanover
2) Portland (these two are very close)
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3) SF Bay Area
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4) Ottawa
Honestly, I love living here. You're surrounded by great people and beautiful surroundings. There's no crime and (almost) no traffic. If you like the outdoors, you will love Hanover. Hanover is in the middle of nowhere, but because Dartmouth and DHMC are here, it's a very nice middle of nowhere with quite a few "big city"
amenities without the downsides of a big city. Maybe it's because I'm very busy, but I'm never bored here. I almost didn't apply to Dartmouth because I thought of Hanover as being in the middle of nowhere, but I'm very glad I'm here.
That being said, if you MUST be in a city, you will hate it here. There's one (sketchy) club within an hour of the school. There are "only" (more than enough for me) about a half dozen bars in the area. You will constantly bump into people you know. Also, you'd better enjoy winter/snow, or at least be able to deal with it.
Anyway, I love it here and it's one of the few places where I could see myself settling down eventually.
As for distances: ~2 hours to Boston, 3 to Montreal.
Smaller cities: Manchester/Concord: ~1 hour, Burlington: ~90 minutes.
I'd be happy to answer any questions you may have about Dartmouth/the area.