My granddaughter has been accepted at Green Mountain College, Poultney, Vermont. I'm poking around looking for good ways to get there!
She and her parents would like to first visit, in the next month or so, before she decides - they haven't yet seen the school. (It's description sounds very wonderful!).
So, we all live in Santa Cruz - best airport is SJC. SFO, OAK, MRY also possibilities. It seems clear a car rental would be necessary at destination, and I'm wondering where you think good to fly into would be?
Poultney is on the far western side of Vermont, right on the NY border. Closest airports are BTV and ALB, although MHT is a close third. One of those would be your closest option, and all should have plentiful car rental options.
And having been there (not as a student, but for a weekend event a few years ago), the campus is quite nice.
According to Google, Poultney is an hour and a half from either ALB, BTV or LEB, but three hours from MHT or BDL, three and a half from BOS, or four and a half from JFK.
With those timings, I'd suggest taking your pick between getting a flight with one change to ALB/BTV or a nonstop flight to BOS. The total journey time is likely to be very similar. (As a rule of thumb, a connection on a transcon generally adds about two hours to the total journey time.)
Unfortunately, I don't think anyone is operating the SJC-BOS 'nerd bird' any more (which is a source of considerable angst to my colleagues!) so for a nonstopper you'd have to go to SFO, where they're fairly plentiful. More likely you'd take one of many possibilities from SJC to ALB. Most airlines will do that with one connection somewhere in the Midwest.
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FWIW, if the travelers aren't used to driving in the snow, the easiest drive, IMO, will be from Albany, though Burlington would be a decent option. Virtually every other airport option will put you in a position to drive westbound across VT (which has many scenic drives), but will be mountain routes. US 4 from the I89-I91 junction has a lot of mountains (it goes right past Killington ski area) and can get pretty nasty pretty quickly.
Coming up from Albany puts you on I-87, which is decently maintained, then across NY 149 to US4 eastbound. Having done most of these routes in the winter, I can assure you that that's quite a bit easier than a lot of the other options.