Nestled onto Route 4, the dividing line between northern and southern Vermont, Woodstock, a historic town that very well defines country chic. Here, the restaurants all sport linen (or adorably retro marble tables), the inns all have bath amenities worth snagging, and the artists all have city agents. Even the year-round residents in Woodstock are usually ex-Manhattan performance artists or creative types who’ve come to live their lifelong dream of opening a patisserie, antiques shop, or country B&B.
But let there be no doubt: This is the Vermont  you came here to see—ridiculously perfect white-steepled churches, farmhouses with cows grazing outside, and of course antiques stores and crafts shops as far as your wallet can take you.
A must-stop site is Quechee Gorge , where trails plummet from the road hundreds of feet down to a rushing white-water river. This is prime ski country, with the granddaddy of all New England ski resorts, Killington , stretching its grooming equipment over six whole mountains.
To get to Woodstock from Boston , take I-93 to Concord  (70 mi., 1 hr. 15 min.), then I-89 to White River Junction  (70 mi., 1 hr. 15 min.), before exiting onto Route 4 west for another 10 miles (20 min.). The total trip from Boston to Woodstock is about 140 miles (2 hrs. 45 min.).