FuelFor breakfast and lunch, you can't miss Mountain Creamery (33 Central St., 802-457-1715, sandwiches about $10), run by Boris Pilsmaker, a native of Milton, who also owns a farm in Killington that provides much of his food, including meat for whopping roast beef, ham, and turkey sandwiches. Speaking of whopping, leave room for homemade apple pie, the biggest you're likely ever to see, 3 1/2 pounds of locally grown apples expanding a flaky crust to near-bursting. Bentley's (3 Elm St., 802-457-3232, www.bentleysrestaurant.com, lunches $9.50-$12.95, dinner entrees $18.95-$26.95) has been a Woodstock favorite for more than 30 years, with its dark, moody interior and Victorian sofas, oriental rugs, and antique lamps. Bentley's custom brews its own ale and features dancing on Saturday nights with the occasional live entertainment. Fine dining abounds throughout town, including The Lauren Restaurant (3 Church St., 802-457-1925, www.thelaureninn.com/dining.html, small plates $8-$13, large plates $22-$29), located in a renovated village inn on 2 sweeping acres overlooking the Ottauquechee River that serves top-shelf food small in portions but huge in taste. Try the potato wedges cooked crisp in duck fat and you'll never want them any other way. Another popular Woodstock eatery is The Prince & The Pauper Restaurant (24 Elm St., 802-457-1818, www.princeandpauper.com, prix-fixe dinners $48), which virtually all locals recommend. Its popularity warrants reservations, particularly in leaf-peeping season. Expensive and worth it, but do check out the less-expensive and just-as-tasty bistro menu.
Budding beauty
Quintessential New England town is a sight to see
SpendYou can't shop in Woodstock without stopping at Gillingham & Sons (16 Elm St., 802-457-2100, www.gilling hams.com), one of the state's oldest general stores, a rambling, seven-room building that is a National Historic Landmark and sells just about everything under the sun, from a range of beers to gift items, Vermont foodstuffs to children's toys. Collective: The Art of Craft (47 Central St., 802-457-1298, www.collective-theartofcraft.com) is a terrific little artists' cooperative selling jewelry, ceramic goods, handbags, clothing, lamps, and more, in a narrow, easily navigated space in a building right on the Ottauquechee River that courses through downtown. Get your reading needs met at one of Vermont's oldest independently owned bookstores, The Yankee Bookshop (12 Central St., 802-457-2411, www.yankeebookshop.com). Established in 1935, the store also features a wide assortment of toys, learning tools, kites, and spinning hanging ornaments.
PlayA Woodstock winter can be pretty chilly (the area averages nearly 6 feet of snow a year), but one place to be cold on purpose is Union Arena (496-3 Woodstock Road, 802-457-2500, www.unionarena.org), a popular skating rink and community center, and the site in 2009 for a winter triathlon of skating, cross-country skiing, and snowshoeing. Bikes abound in Woodstock and a good place to rent or buy is The Start House Ski and Bike (28 Central St., 802-457-3377, www.thestarthouseskiand bike.com). The staff will also advise you on where to ride, including the nearby River Road on the Ottauquechee, voted one of the state's best rides by Vermont magazine.