An Awesome Long Weekend Itinerary in Portland & Willamette Valley

I am notoriously bad about exploring some of the amazing destinations in my own country.  So I made it one of my goals last year to visit a place in the U.S. that had been tugging at me for quite a long time.  It was a no-brainer because I tend to prefer Willamette pinot noirs over California or European ones, and had been dying to try some of Portland’s coffee and food hot spots.  So I decided to put a girls’ trip together with a Willamette and Portland itinerary!

This Willamette Valley and Portland itinerary is so great because there is just an embarrassment of travel riches and everything is SO close…from hipster Portland with its food and beer scene, to Willamette Valley’s wineries, to the natural beauty of the hiking trails, waterfalls, and beautiful Oregon coast, you could spend weeks here exploring but can also really accomplish a ton in a long weekend!

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How to plan your Willamette Valley & Portland itinerary

We didn’t make it to the coast on just a 3-day weekend, but you could easily start there or tack it on at the end if you have a bit more time.  For just three days, I recommend focusing on Portland and Willamette, and getting some hiking and waterfalls in in-between.

If you’re planning a bigger Oregon itinerary, here are more tips for you!

Hiking Oregon’s Stunning Trail of Ten Falls

Feeling Hip(ster) in Portland’s Food & Beer Scene

A Weekend of Wine in Willamette Valley

An Epic Oregon Coast Road Trip Itinerary

Why You Have to Experience an Oregon Coast Sunset in Your Life

How to Visit Thor’s Well on Oregon’s Coast

When to visit

The area is fairly temperate, so you can really be comfortable a lot of the year.  October through January tends to be rainy (and obviously chilly), so if you want to spend a ton of time outdoors it might not be best (plus you won’t experience the best of the vineyards.

May through August are your warmest months, though also will have the most tourists.  Think about Memorial Day, when the winery season is really kicking off, or September, when they’re harvesting the grapes as well.

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Where to stay

In the Willamette Valley I absolutely loved our cute little Airbnb, and a rental like that is a great option because it’s a fairly rural area.  Because it’s a tourist region there are some hotels, but they’re definitely not as plentiful.  Many people do day trips from Portland instead, but I think it’s worth staying out here.

If you’re looking for a special experience in the Willamette Valley, consider The Allison Inn & Spa (where we ate dinner, below).  It looked absolutely charming and would be a great splurge option (like for a romantic weekend).

In Portland there are TONS of great options.  For us, we stayed at the Portland Downtown Marriott Waterfront (see TripAdvisor reviews), and it perfectly suited our needs…awesome location, spacious, comfortable.  If your goal is to explore the downtown area on foot, make sure your location reflects that.

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How to structure your itinerary

It depends on weather and a few other things, but the order of our itinerary was perfect.

• We arrived in Portland on Friday evening (I’d recommend late afternoon if you can swing it), got the rental car, and drove the hour or so down to our cute little Airbnb in Willamette.
• We spent all day Saturday visiting wineries, swung by another Sunday morning, then dedicated a big chunk of Sunday to hiking.
• Then we completed the loop and got back to Portland Sunday evening, checked into our hotel, and spent the evening and most of Monday exploring the city.
  • You could return your rental car before getting to Portland, and we considered it, but for four people and luggage just figured it was easier to pay the $40 valet parking at the hotel vs. taking public transportation back to the airport.
• If you had a few more days, throw in some additional hiking and some time on the coast.

Here is how we did our itinerary, and I’d definitely recommend it!

Day 1:  Willamette Valley

If you’re going to be sipping on wine all day, a big breakfast is a must.  And if you’re staying in Sherwood or nearby, I highly recommend hitting up Fat Milo’s for breakfast.

I had the best chicken & waffles I’ve ever eaten (which is saying something from a Southerner), and my friends said the chilaques were amazing.  It’s got a great local diner feel, service is fast.  Only downside is no espresso drinks 🙂 (#firstworldproblems)

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We wanted to experience as many wineries as possible in our limited time, and it was definitely doable since a lot of them are so close to each other.  With over 400 wineries in the Willamette area, it was kind of overwhelming to even know where to start, and I’d done a ton of research beforehand.

This helped guide us, particularly for starting out, but we also kind of followed our impulses when someone gave us a recommendation.  I have a full post about our time in Willamette here that gets even deeper into each of the wineries and how we liked it!

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We couldn’t have asked for a prettier day to explore the area (though a bit on the hot side, for May), and we really made the most of our limited time.  We did stay in a fairly focused area, to avoid spending tons of time driving.

Of all the ones we visited, we were least impressed by Montinore from an ambiance/experience standpoint, so I’d give that one a skip.

The wineries we visited:

• Penner-Ash
• Trisaetum
• Styring
• Montinore (skip)
• Patton Valley
• Ann Amie (on day 2)

Since Willamette is also a big farm-to-table foodie destination, we’d done our research ahead of time and booked a dinner at Jory, in the Allison Inn.

Because we squeezed Patton Valley in at like 4:45 on Saturday we ended up careening into the parking lot at Jory, and then hastily changed clothes in the car/parking lot (classy!) and headed in.

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Jory’s food and service were both exceptional.  We snagged a sweet table right by the patio, so got to watch a gorgeous sunset, and the waiters helped us set up a little birthday surprise for one of the girls in our party.

It was such a lovely, relaxing experience and I’d highly recommend it if you’re looking for a bit of a splurge or celebrating a special occasion.

Absolutely stuffed and super tired from day drinking and a big dinner, we went back to our cool winery Airbnb (if you’ve never tried Airbnb, you can get a discount here) and tried not to fall asleep while watching The Wedding Planner, like the ballers we are.

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Day 2:  A little wine, and epic waterfall hiking

Fat Milo’s drew us back for round two of chicken & waffles (I know, I know, we should have tried somewhere new), and then we decided to try out one more winery before hitting the hiking trails.  We’d met a cool older lady in a cat sweater the day before who had steered us toward not only Styring (which her family used to own) but also Ann Amie for the views.

The patio was awesome indeed, though the wine and overall views to me weren’t anything special vs. Penner-Ash and it was further out.  Gorgeous day, though (hot as nobody’s business).

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Sufficiently sweaty and running later than planned, we drove over the Silver Falls State Park to traverse the Trail of Ten Falls.  I’d done TONS of research on waterfall hiking trail options before the trip, and it was so hard to choose between the dozens of beautiful hikes.

We were tempted to do either Multomnah or Punch Bowl Falls, two of the most well-known waterfalls in the Columbia River Gorge area.  But we decided to go a little more under-the-radar and get more bang for our buck—10 falls for the price of 1.

Hiking the Trail of Ten Falls, Silver Falls State Park

There’s a huge parking lot at the trailhead, though finding a spot was tricky since it was mid-afternoon on a holiday weekend.  We finally did, though, and hit the trail immediately.

Most of the trail is shaded, so it was a nice respite from the heat, and not nearly as crowded as one of the most popular trails would have been.

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This post goes into our hike and each of the waterfalls, and also a mistake we made in the route (got a little confused and missed a turn, which ate up time).

We were a bit rushed because we’d gotten a late start and wanted to get to Portland before nightfall to make it easier to find our hotel.  So we booked it along the path and caught 7 out of the 10 falls—our route mistake cost us the others, but we saw the best ones so didn’t feel cheated.

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Sweaty and dirtier than we’d anticipated, we piled back in the car and drove the hour or so to Portland.

After getting checked in at our hotel (the Portland Downtown Marriott Waterfront), got cleaned up, and headed to Huber’s for dinner (an institution) and Departures for a rooftop bar view.  I’d give both a skip—Huber’s food was edible but nothing special, and Departures was crowded, windy, chilly, and full of…not my kind of people.

Day 3:  A speedy Portland itinerary

Our last day on the West Coast dawned overcast but not too chilly.  I was up before everyone else so went for a walk over the bridge and got some delicious coffee and pastries from Coava.  Once I’d rounded up my peeps, we stopped by Heart as well, and didn’t get to catch several other coffee shops that came highly recommended.

I’ve provided more recommendations in this detailed post on how to spend 24 hours in Portland.

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A stop at Blue Star Donuts was definitely non-negotiable (sooooo yummy), and then we headed to our first brewery.  We were looking for good food, which forced our hand a little, and ended up at Deschutes.

But later we went to the much smaller 10 Barrel Brewing on a whim, and were delighted by the fun rooftop patio on what ended up being a gorgeous day.

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Most of our Portland time was a blur of coffee, donuts, beer, fried food, beer, and gelato.  We were hyped up on sugar and caffeine by the end of it, but felt we’d done our best in the short time we had.

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Walking around the Pearl District and soaking in the distinctive industrial vibe was great, and we really enjoyed walking along the waterfront right near our hotel.

Downtown Portland is super walkable, though you can fairly easily get an Uber if you need to get somewhere really quickly.

So there you have it—a perfect 3-day weekend itinerary for Portland and Willamette Valley.  Again, if you have an extra day or two then I highly suggest getting out to the beautiful Oregon coast as well.  But with just a holiday weekend you can see and do so much in this beautiful little corner of the country!

As you saw throughout the post, I linked to more detailed posts on each of the different parts of our Willamette & Portland itinerary, and I’m happy to answer any questions you have while planning your own adventure…just hit me up in the comments!  If there are must-do things we missed, let me know as well, because I definitely see a return trip in my future!

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