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First of all, Bard is located in Red Hook (Annandale), NY, not in Potsdam or Canton, so I wouldn't exactly say it's in the middle of nowhere. Nearest large town is Kingston, about 15 minutes away on the west side of the Hudson. You are also 10 - 20 minutes from Rhinebeck and Hudson, which are somewhat artsy communities with a range of decent restaurants and niche shopping opportunities.
As for how to get to NYC, Bard is 10-15 minutes from the Rhinecliff Amtrak station. If you can get a ride to Poughkeepsie (30 minutes south of Bard) you can get a Metro North commuter train to Penn Station. Metro North is cheaper and has more frequent service than Amtrak. As for Boston, that's a little more difficult. I'd check the ride board if you really feel the need to go.
Winters at Bard are slightly colder than winters in NYC (again, Bard is NOT located in the real Upstate NY region) and snowfall averages 2-3 feet a year (rarely at once -- snowcover varies throughout the winter). If you want a taste of the true Upstate NY winter you need to go a few hundred miles to the NW to Syracuse or U of Rochester.
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