Sounds like a fun trip you have planned. My top recommendation for a trip that has all of the above (out of the way pretty wineries, good food, interesting accommodations and a close flight) would be for you to focus your trip on the southern portion of the Willamette Valley.
The entire Willamette Valley is more than 100 miles long, with wonderful wineries throughout. I don’t know how long your trip will be, but if you don’t want to spend your entire trip driving, I’d say pick one portion of the Willamette Valley and focus your time a little bit. If you choose to explore the south Willamette wineries, you can fly in to Eugene, a smaller airport that’s a breeze to fly in and out of. You can be at a winery within 30 minutes of landing if you choose!
Here’s a guide to wineries in the south part of the Willamette Valley.
One of my favorites in this area is King Estate, which is absolutely beautiful and has a top-notch restaurant on-site (one of only a handful of wineries in Oregon to have a full on-site restaurant). Visit, take a tour, taste some wine and get a meal while you’re there–it’s a lovely experience from start to finish.
Another vineyard very close to King Estate but that offers a very different experience is Sweet Cheeks.Winery. This is a much smaller, more intimate winery. It’s also in a pretty spot, and it has a relaxed, friendly vibe that makes you want to linger with friends all day.
The south Willamette Valley also has some great options for unique accommodations. As a matter of fact, Sweet Cheeks Winery has a farmhouse or a vacation loft on their property that you can rent.
Another nice option is the Campbell House Inn, which is a B&B in the city of Eugene, walking distance from some delightful restaurants. A few of my favorite places to eat in Eugene:
- Party Downtown: funky, unique, local cuisine. Try the chef’s tasting menu–the chef selects your menu for the evening, so your whole meal becomes one tasty surprise after another.
- Marche: Classic French-inspired food with amazing attention to detail and fine local ingredients.
- Oregon Electric Station: Beautiful food in a beautiful building–a renovated turn of the century train station
You also mentioned quaint shops. I’d recommend you visit the little town of Coburg. It’s a tiny historic town just outside Eugene that’s full of antique and vintage shops. I also love shopping at the Fifth Street Public Market in Eugene, especially the Provisions Market Hall. I love food, wine and cooking, and the Provisions Market Hall is full of all kinds of gourmet items, cookbooks, and gorgeous housewares.
This is just a little overview of things to see and do in the south Willamette Valley, but for even more info I’d suggest the South Willamette Wineries website I included above, or the Eugene, Cascades & Coast website for a really thorough look at attractions in the area.
If the south Willamette Valley doesn’t fit your travel plans and you want to explore some of the other parts of this region, feel free to write back for more recommendations, or check out www.oregonwinecountry.org — this site gives a great overview of all regions of the Willamette Valley and has a neat trip-planning tool that lets you map out routes that include wineries, food, lodging, and things to see and do.