I went to Dartmouth undergrad, so just wanted to throw my $.02 in about the area. Dartmouth is actually two easy-hours driving from Boston and four from Montreal and five from NYC.
As for the cultural life of Hanover, the College has a ton of great acts and concerts that come through. The Dartmouth Film Society is particular great, not that med school would afford much time for going to the movies.
Im originally from Virginia and have spent time in Charlottesville. Overall, I would have to say Hanover and Charlottesville strike me as pretty similar places, give or take a few thousand undergrads.
Truth-in-advertising, I was waitlisted at UVa and am still waiting to hear from DMS. One thing that came up in during my interview at UVa was the fact that some of the 3rd year rotations are in the far reaches of Virginia. DMS also has away-rotations, so I guess it is just a basic concern of less-urban schools. I bring it up because during my tour of UVa, the away rotations were mentioned by each of the three tour guides as something they had wished they had known about the school before they got there.
In general, both are great schools in great towns. Hard to go wrong.