Well I can’t speak for Kenyon but my son is a senior at Vassar . Big difference is Vassar has no fraternities sororities and i hear that this is a big part of Kenyon social life but in a alternative fashion. Best word to describe Vassar is iconoclastic. Very artsy very counter culture theater is big sports are not. Not much to do in Poughkeepsie per say except all that suburban America has to offer but lots to do in the Hudson river valley and people really do go into NY by train on the prettiest 90 minutes of your life. Housing at Vassar is fantastic with lots of public space and the senior housing is cool where they have apartments with kitchen separate from the rest of campus. Lots of really great historical sites all around Poughkeepsie and the hudson valley has always been the center of the arts in America. We went to New Palz a couple of times nice state university there. Rhinebeck a couple of times. Very scenic area and if you have a car everything that is anything, NY, Boston, Yale, East Coast, in striking distance. Also Vassar is large by liberal arts college standards. Lacking fraternities there are not tons of large parties to go to. Some school sponsored events there are always Halloween parties but not big parties every weekend as far as I can tell. Mostly people are in clubs formal or informal. Son ended up sticking with people on the wellness floor and being in a group playing D&D in one of the public rooms in the dorm and doing a couple of plays every year. Hudson valley us so beautiful.