Yes, I understand there's some interesting wine country just south of Portland so maybe it's a better idea to turn around at Bend, head directly north and over the mountains towards the coast, skipping out Eugene
It's more than interesting - it's the best Pinot Noir region in the US. Definitely worth visiting but the prices are a bit dear. I can highly recommend McMinnville as a place to stay.
Yes, I understand there's some interesting wine country just south of Portland so maybe it's a better idea to turn around at Bend, head directly north and over the mountains towards the coast, skipping out Eugene