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On the road into Woodstock (you'll see the signs), the Simon Pearce Restaurant (reservations recommended) in Quechee offers a unique dining experience, and was recently named one of America's Most Romantic Restaurants by Travel + Leisure. Enjoy a gourmet meal in this idyllic location -- a restored mill full of blond wood & exposed brick -- perched over the falls of the Ottauquechee River. Afterwards, head downstairs to see (and perhaps purchase?) a selection of the famous glassmaker's wares.
Tiny Wasp's Snack Bar is a classic greasy spoon. Just after the Sunoco station on the left after you round the final bend into town, if you blink you'll miss it. Once you do find it, belly-up to the 10-stool bar for some eggs & hash browns for breakfast, or a solid lunch of grilled cheese & chicken soup.
Just before entering the center of Woodstock proper, you'll find Osteria Pane e Salute (reservations recommended). This Italian bistro is popular with locals & visitors alike, and has received high praise from a number of publications including Bon Appetit, The Boston Globe, Food and Wine, Elle Decor, and Travel + Leisure. The menu's focus is on regional dishes & local ingredients (they grow many of their own), and reflects the owners' passion for the slow food movement.
The Prince and the Pauper has a traditional dining room as well as a cozy & comfortable bar area (full menu available here as well.) The prix-fixe offering changes nightly, and always includes delicious regional fare. There is also a bistro menu -- local favorites include the Maine Crab Cakes and Glazed Salmon. Excellent wine list.
The Mountain Creamery -- as the name suggests -- sells delicious home-made ice cream cones & sundaes (in the summer months a dedicated parlour opens in the basement), but locals especially love the big country breakfasts, simple lunches, and home-baked pies.
The Woodstock Inn & Resort has undergone a significant transformation in the past few years. The inn added a new Spa, as well as a new restaurant, The Red Rooster. The Red Rooster's dining room is light & airy, described as 'casually elegant', and is an excellent choice for families with young children. There's a chic bar area at the front of the restaurant -- the perfect place for a glass of wine or pre-dinner cocktail. Although change is good, it's a good thing that Richardson's Tavern has remained largely the same, with certain small improvements like the addition of more comfortable chairs and better seating around the wood-burning fireplace. The bartender is known for an excellent whiskey sour, and the Inn offers an extensive wine selection. The Tavern is a great choice year-round (exceptional in fall & winter) for lighter fare. Local favorites include the Inn Burger, Iceberg Wedge, and Fondue.
During the summer months, The White Cottage (just west of the Village on Route 4 at 462 Woodstock Road) is a great choice for a casual meal. The Cottage is famous for its standard '50's drive-in fare -- hamburgers, hot dogs, and fried clam rolls (strips or whole bellies). Picnic tables are set up around the restaurant for pleasant outdoor dining. And on sunny, summer evenings line up with the locals for a Gifford's ice cream cone.
In South Woodstock, a small hamlet a few miles down Route 106 and home of the Green Mountain Horse Association, the South Woodstock Country Store (10673 South Road) is a must. For breakfast, sit down with a Bill Clinton (egg sandwich with bacon, tomato & avocado) or carry out a cinnamon donut & coffee with your New York Times. Phil's pizza is legendary for lunch, but get there early because it sells out quickly. For dinner try The Kedron Valley Inn, and dine in either the cozy tavern or classic New England dining room. And in the summer months, enjoy drinks & dinner on the front porch. Although it has undergone a number of ownership changes in recent years, The Kedron seems to have settled into a solid rhythm under current ownership and remains a local favorite.
Just beyond South Woodstock, but still on Route 106, is Keeper's Country Cafe in Reading. Open for dinner Tuesday - Saturday (and the occasional Sunday), Keeper's is perfect for families or large groups, and known locally for excellent burgers, salads, and nightly specials.
Finally, not at all far to the north of Woodstock on Route 12 is The Barnard Inn (since 1796). The Dining Room (complete with wood-burning fireplace) offers a 3 or 4-course dinner and is open Thursday - Saturday. Max's Tavern (Tuesday - Saturday) is a more casual option. Steamed mussels, pork chops, and the wienerschnitzel are local favorites (as well as the home-made desserts.)