A day away from the hill at Killington or Suicide Six offers a chance to discover why, as the local saying goes, "the good people of Woodstock have less incentive than others to yearn for heaven. True, there may be no lovelier village in Vermont, but that's no accident. Its most famous resident, 94-year-old Laurance Rockefeller, married a local girl—and fell for her hometown, as well. They built a mansion on the edge of town, then saw to it that power lines were buried and historic architecture was preserved. Today, Woodstock is tidy and thriving, well worth a day of exploration.Slip in while last night's fairy dusting of powder still coats the streets and before locals snap up the 10 stools at Wasp's Diner's purple Formica counter. Fortified by a plate of eggs, fried hamsteak and a slice of warm apple pie (yes, you do want Vermont cheddar with that), you can light out for the village's historic core.
At the center of things is still the Woodstock Town Crier, a blackboard on the village green where local news finds an audience. Warm up with an almond cappuccino at Pane e Salute pasticceria, then prepare to part with some dough: Fashionistas will find Italian sportswear at Morgan-Ballou and vintage lace and linen at Who Is Sylvia? Contemporary furniture by Charles Shackleton is on display at his shop in town (as well as at The Mill in nearby Bridgewater). Or, if your tastes veer toward country antique, ogle the goods at Wigren-Barlow. Vermont's oldest general store, F.H. Gillingham, is the spot to replenish your maple syrup reserves.
At lunch, cross yawning Quechee Gorge to Simon Pearce, where working potters and glassblowers put on a show inside a restored woolen mill in Quechee. Browse their wares in the shop, then tuck into seasonal fare in the cafe overlooking the Ottauquechee River. Local lore is the order of the afternoon, with a visit to the Woodstock Historical Society and a stroll past the circa-1800 Colonial and Federal homes near The Green.
For a casual dinner, Bentley's draws a nice Long Trail Amber (it's brewed just down the road); pair it with their New England crab cakes. This town pulls the curtains early, so unwind with a single malt at Richardson's Tavern at the Woodstock Inn—a fine way to gear up for tomorrow's action back on the slopes.
Click below for a slideshow and details of Woodstock, Vt.