I live about 15 minutes from Killington. You'll enjoy the natives. Nothing but a bunch of fat, smelly, toothless, tobacco-chewing, nascar-watching inbred hicks. And the guys are just as bad.
Seriously, there are some OK clubs on the Killington Access Road.
Wobbly Barn, Nightspot/Outback, Pickle Barrel (don't worry, not a gay bar), pretty much any of the clubs will be hopping. If you want Italian food, try out Peppino's
If you venture down into Rutland here are a couple of recommendations:
Good restaurant - Royal's Hearthside.
Good pizza joints - Ramunto's, Ted's, A Crust Above.
Good sub shop - Gill's Delicatessen.
Good place to watch a game - Sabby's.
Most likely area in town to score heroin or catch an STD- State St./Baxter St.
As far as attractions - well, there just aren't many.
http://www.vtliving.com/attractions/index.shtml