The Bear Cafe at 295 Tinker Street has an inviting & cozy ambiance. The rectangular bar in the middle of the restaurant is a great place to grab an appetizer, meet the locals and have a drink whilst the sun is setting. Alternatively, sit at a table overlooking the babbling stream and enjoy a scrumptious 3 course dinner. They often have specials on Monday nights and change their menu often. The mussels are always a good choice. It can get pretty busy, especially on show nights at The Bearsville Theater (which is located next door, definitely check that out too!); we recommend making a reservation for dinner during the summer and on show nights.
The Red Onion is another Woodstock staple. It's actually located on the Woodstock/Saugerties line, 1654 Rt 212 @Glasco Turnpike. The menu changes daily, we typically go for their seafood special. This is a great restaurant for a romantic meal out. Cucina has a lovely wrap around veranda, which is perfect to sit out on and have dinner, it has a spacious dining room and a friendly bar area. If you need to try and please everyone this is a good choice! The menu is varied, and includes: interesting flavored pizzas (caprina goat cheese, fig-rosemary spread, pear, arugula, truffle oil is delicious), pastas, meat/fish dishes and yummy salads (recommend the kale!).
For cafes with a more casual atmosphere we recommend: Oriele 9 (b/fast & lunch only), Joshua's, Yum Yum Noodle Bar, The Garden Cafe (vegan/vegetarian), Shindig (comfort food). All theses cafes are located in the center of Woodstock and most are open for dinner.
We finally have a late night bar in Woodstock! The Station Bar & Curio (101 Tinker St) is open until 2AM, serves food & has a pool table. We can't wait to check it out!
If you want a little change of scenery Kingston (20 mins from Woodstock) has some very good restaurants, including: Sushimakio (sushi), Boitson's (American) and there's always Peekamoose in Big Indian.
If you are from the city, please remember this is the country, and service finishes early (around 9:30 or 10:00 PM), so don't leave it too late!