Things are moving so fast in Bend that this will be outdated by the time it's sent. Recently, the two best places to try a variety of wines are right next door: Merenda and Vino Mercado. Vino has changed concepts since we were last there, so who knows. Merenda has 2oz tastes that are priced 1/3 of a 6oz glass, which is priced 1/4 of a bottle. So you can try a bunch at reasonable prices. Also good appetizers, esp at happy hour 4-6 daily.
For restaurants, try Control F for Bend to look at recent posts. If that doesn't work anymore with the new website, post back and we can recap.