Here's a quick-ish update on our trip. We just did one day trip to the Willamette Valley from Portland.
We started the morning at Durant Hill Olive Mill and Vineyard. We did the tour of the mill and saw some of the olive trees. The tour guide was very knowledgeable and the area is gorgeous. We did a quick olive oil and vinegar tasting at the end (delicious!), but the tour was a little longer than planned, so we had to hurry to the next destination.
Next we stopped at Stoller. The patio and view was amazing and the service was great. There is a very small food menu. We had a flatbread with brie, prosciutto, grapes, and strawberries. It was fine, but nothing amazing. We really liked the chardonnays at Stoller. The Willamette Valley tends to do a crisp, non-oaky/creamy Chardonnay, which is what I prefer. I didn't love their rose, but the pinot noirs were great.
Next we went to Anderson Family. It's a small vineyard. The "tasting room" is just a small bar in a big open space with wine barrels that are currently fermenting. The people running the tasting are the couple (Anderson) who own the whole place. They have been there since the 70s. We were able to smell and listen to the wine as it fermented. We did a vertical tasting of their chardonnay and pinot noir. They are, of course, very knowledgeable about the vintages and the area. The pinot noir was especially light, but everything was very good.
Our next stop was Winderlea. Our server was again very knowledgeable. There we did a horizontal tasting of wines from grapes all grown on site. I think they also have a tasting where they give you the descriptions of the wines and then you do a blind tasting to match the wines to the vintage and description, though we didn't do that one. There is also no food at this tasting room.
Before our last wine tasting, we stopped at Briar Rose Creamery. I'm not sure if there was more a shop pre-covid, but it was just a stand with their cheeses out, pre-packaged, to purchase. They also had a few types of sausage and crackers for purchase. I forgot to write down which two we bought. They were good, but nothing amazing. I'm not sure it was worth the stop. The person running the stand didn't seem to want to chitchat about the cheese.
Our last stop was Rex Hill. This was the only stop where our server was not very knowledgeable or helpful. They have a limited food menu. We had some roasted hazelnuts and bread/olive oil, which were both very good. They don't have any wines in the tasting that are grown solely from their grapes, but all the wines were very good. They have a very popular sparkling rose.
There were so many places we wanted to go to but didn't have time (or the blood alcohol level) for. We were very happy with how we divided up our Portland trip, but if we'd had another day, I would have loved another day of wine tastings.