The towns I love for wine tasting are Newberg, McMinnville and Dundee. All three are driving distance of each other in Yamhill County.
For dinner, The Painted Lady is seriously top notch. Recipe- A Neighborhood Kitchen is also very nice. Downtown Newberg has many tasting rooms all located within walking distance of each other. You can see a map here: newbergdowntown.org/wine-tasting/
In McMinnville, walk the downtown area where you can shop, taste wine and eat at wonderful restaurants. Here you can stay at the Mattey House which is a B&B located in a beautiful 1892 Queen Anne Victorian Home on 10 acres. Or perhaps you would prefer Youngberg Hill Vineyards and Inn, a 22 year old organic vineyard and tasting room with deluxe accommodations. There is also a classic European style B & B called The Steiger Haus that is located in downtown McMinnville. There are many options for meals in this town but a few of my favorites are: Community Plate (lunch only), Nick’s Italian Café and Bistro Maison. Here is a guide to downtown McMinville: downtownmcminnville.com/explore
If you make a stop in Dundee, The Dundee Manor is a nice place to stay, as is the Black Walnut Inn. While in town, you can even visit Herbert Hoover’s (America’s 31st president) boyhood home. There is no shortage of good restaurants in the area. Thistle, Tina’s and the Dundee Bistro are all great choices. Red Hills Market is good for casual dining.