Three Days in Willamette Valley, Oregon

Visiting Willamette Valley? There’s plenty to do and see in Oregon wine country. Let this three day itinerary, featuring wineries, shops, and accommodations, be your starter guide.

Even though I’ve lived in Portland, Oregon for several years, I have only visited Willamette Valley for a multi day trip on one occasion. All the other visits were day trips or afternoon excursions. You’ll find plenty of great destinations, like incredible wineries, breathtaking views, plant nurseries, local boutiques, and more, in Oregon wine country. What’s on your list?

This itinerary is based on a three day wine country getaway I took with a friend. Please keep in mind that places may have closed or changed their offerings, on top of the constantly evolving covid safety protocols. I recommend looking up these places individually as you plan your visit to Willamette Valley.

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Willamette Valley Day 1

An hour outside Portland, our first stop was Red Hills Market in Dundee. This country style market is a one-stop-shop for seasonal produce, craft beer and wine, or a quick sandwich lunch before visiting a nearby winery. They’re also known for their wood fired pizzas. I enjoyed an open face mashed chickpea sandwich made with excellent bread.

Our next stop was Dobbes Family Estate, located a stone’s throw from Red Hills Market. It was a weekday, so we pretty much had the entire outdoor Hideaway patio space to ourselves. Reservations are required for the seasonal tastings. Our flight began with a complex Grenache Blanc before diving into Dobbes signature Pinot Noirs with juicy fruit forward profiles.

After wine tasting, we checked in at The Vintages trailer resort. While staying in a trailer may not be for everyone, it was the most memorable parts of this wine country getaway. Each trailer has a different style, and ours — the 1963 Airstream Overlander — was outfitted with mid-century moden style decor. Trailers come with an outdoor propane grill, dinnerware, and mini fridge, so we stayed in for several meals.

Wine Tasting at Dobbes Winery

Lunch at Red Hills Market

A Look at The Vintages Trailer Resort

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Willamette Valley Day 2

After a morning yoga session and tofu scramble breakfast, we visited the highly acclaimed White Rose Estate in Dayton. While taking in sweeping views of Willamette Valley, we sipped on some of the most exquisite Pinot Noirs I’ve ever tasted. If you’re there with a friend, I recommend each ordering a different flight, so you can experience more wines. Naturally, we picked out a bottle to take home. Mine is still sitting in my wine collection, waiting for a special occasion.

Next, we explored Downtown McMinnville, from Atticus Hotel to local boutiques. Even if you don’t plan on dining or shopping here, it’s fun to walk through Third Street — the main street in historic downtown — for the small-town experience. Next time I visit, I’d love to stay at Atticus Hotel.

For our final stop of the day: McMinnville’s Mac Market. This collaborative market for eating, drinking, and shopping is housed in a beautifully renovated industrial warehouse. I loved the dips with pita bread and gorgeous pasta from Collab Kitchen, gluten-free based goods from the now-closed Flour & Fern (for breakfast the next day), and adorable plant babies and accessories at Sustainable Rituals.

Wine Tasting at White Rose Estate

Vegan Dining at Mac Market

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Willamette Valley Day 3

On our final day, after a decadent breakfast (I had a oat, pecan, chocolate, and coconut caramel treat from Flour & Fern), we headed over to Durant at Red Ridge Farms. Although many people visit to taste wines, Durant is equally as well known for its olive oil and plant nursery. My favorite part of this visit to Durant was exploring the gardens and plant shop.

Next, we ventured to Sokol Blosser Winery, also in Dayton. The estate was picturesque, which is to be expected in wine country, and the architecture was beautiful too. Did you know that Sokol Blosser was the first U.S. winery to receive LEED certification? The wines featured in the self-guided tasting flight with mini bottles were stunning, and I took home a bottle of the rare Estate Muller Thurgau — a new-to-me white grape varietal that wowed me.

On our way back to Portland, we made a quick stop at Wolves & People farmhouse brewery in Newberg. There’s an excellent selection of small batch, wild, wood-aged, and blended beers. Order a few tasters to enjoy in the beer garden. I’ll definitely bring some snacks for my next visit.

Exploring Durant Vineyards

Wine Tasting at Sokol Blosser