Wineries are all around! The Pinot Noir and Chardonnay grape are the most common in the area so you'll find lots of those! Cathedral Ridge Winery is our favorite winery for big bold reds and they have a tasting room in Dundee, OR, which is about an hour drive north of Dallas, OR.
Independence is a cute small town along the Willamette River. It's neighboring Dallas and Salem.
Salem, Oregon is Oregon's capital with a population of about 180k. They have a big downtown area, bubble tea ;), and a walking trail along the Willamette.
Portland, OR is about an hour drive from Dallas/Salem area and there are LOTS of food and drink options, there may be a Timbers (Pro Soccer team) game going on that weekend, and there's always some sort of event.
We live in Forest Grove, OR and LOVE visiting the Sake Distillery! There are only 30 Sake Distilleries in the US (per Google) and this one is in the small town we live! The staff is friendly and the sake is such a delight. They import tons of Japanese Sake too. If you call ahead they'll probably give you a free tour :) It's about an hour away from Dallas/Salem area.