Oregon Itinerary – Portland, Cannon Beach & Willamette Valley

We just got home from the most incredible anniversary trip to Oregon! The Pacific-Northwest has long been a favorite destination of mine and Kevin has never been so it seemed like the perfect getaway to celebrate our second wedding anniversary. Of course we’re also in the midst of COVID-19 so we needed to find a destination that would allow us entry without a quarantine period coming from Chicago.

In the weeks and days leading up to the trip, it wasn’t looking like we’d be able to go due to all the wild fires in the area. At one point only a few days before our trip, Portland recorded the worst air quality of anywhere in the world. However, as luck would have it, the day before our arrival, Oregon received heavy rains washing away the ash and pushing out the smoke. When we landed at PDX Saturday afternoon, the skies were blue, the temperature perfect and there were no lingering signs of the smoke. We really lucked out!

September 19, 2020 – Portland Brewery Tour

After picking up our rental car and checking into Canopy by Hilton Hotel in the Pearl District of Portland, we walked to Deschutes Brewery to grab lunch and begin our self guided brewery tour. We enjoyed both the beer and food and thought they did a good job following all of the COVID dining practices. The tables were distanced, everyone wore masks and it wasn’t overly crowded. Afterwards, we just wandered around Portland. This is something we always do when visiting cities and usually stumble across cute streets, shops and sights but we struggled to do so in Portland. We really liked a stretch of 13th Ave but the streets seemed empty or otherwise filled with homeless people [in tents].

Striking out on pretty much anything else to do in Portland, we made our way to 10 Barrel Brewing for the next stop on our tour. After a quick wait, we were seated on the upstairs patio where we enjoyed our beers and relaxed in the sun. From here, we considered going to Rogue Ales since it’s directly across the street but instead decided to take a small break from drinking and head to Cathedral Park to check out St. John’s Bridge. We arrived just as a small rain shower passed through and were rewarded with a beautiful rainbow.

{St. John’s Bridge from Cathedral Park in Portland, OR}

From here, we crossed the Willamette River to Northeast Portland and visited Ecliptic Brewing. Once again, there was a short wait for a seated table but they do offer standing room barrels where you can drink and eat while you wait. This was the final and favorite stop on our brewery tour. To me, all the beer was good but I’m not much of a beer snob. We simply spent the most time here, learned a bit about the brewery operations from the staff and enjoyed the ambiance, despite the chill that set in as the sun set.

{Ecliptic Brewing in Portland, Oregon}

Exhausted from an early start and long day touring around Portland, we opted for ramen take out from Afuri Izakaya. I know Portland is famous for good food and we could have chosen better but we struggled to find something open and available. Plus, we were craving either ramen or thai food so that helped narrow things down. If I’m being honest, it wasn’t my favorite ramen. I found it too spicy for my linking and generally don’t love eating ramen via take out.

September 20, 2020 – Cannon Beach & Ecola State Park

We woke up early the next morning due to the time change and decided to go out in search of caffein and a cute coffee shop. From our hotel, we walked to Never Coffee Lab and while I can’t speak to the quality of the coffee since I always order a Chai Latte, overall it wasn’t anything that unique. Then, because I’m a little neurotic, I made Kevin go to another coffee shop in search of a “cute latte shot” so we ended up at Good Coffee. Here I decided to try one of their seasonal drinks but it was a little too rich for me and still wasn’t that “cute latte shot” I was after. I guess it wasn’t meant to be.

{Never Coffee Lab in Portland, Oregon}

Then we hit the road to Cannon Beach! On our way, we booked a hotel through the HotelTonight app at Cannon Beach Hotel Lodgings. Once we arrived and checked into our hotel, we walked next door to Seashore Bagel Deli & Espresso. We weren’t looking for anything fancy, just something quick and easy and this place fit the bill. Reading the reviews in hindsight, I tend to agree with some of the criticism about the quality of the bagels, hours of operation and price point.

Full from lunch, we set out for Ecola State Park for an afternoon hike. I was hoping to do the Crescent Beach Trail so we could explore the beach as well but it’s currently closed. We ended up parking at the Ecola Viewpoint parking lot and took the trail towards Indian Beach. I couldn’t find this exact trail online but from what we observed, it’s a frequently used, moderate, dog friendly trail that runs mostly inland with only an occasional view of the coastline. We did not go all the way to Indian Beach and turned around after about 40 minutes because it was getting pretty muddy. When we returned to town, we took a long walk along Cannon Beach taking in the beautiful sight of Haystack Rock and the surrounding areas.

After freshening up back at the hotel, we set out to explore the town of Cannon Beach. I was surprised by the charming and elegant cedar shingle homes draped in hydrangea bushes. It gave me major Hamptons vibes but in a more humble way. The town was equally as cute and filled with candy shops, ice cream parlors, tasty looking restaurants. We got a scoop of ice cream from Chillin at the Beach while we strolled.

And then because we still had some time to kill before our dinner reservations, we grabbed beers from Pelican Brewing and walked across the street to enjoy them on the beach as the sun began to set. That night we had a really enjoyable dinner at Wayfarer Restaurant & Lounge. They even remembered our wedding anniversary and surprised us with festively decorated plates that our food arrived on.

{Dinner at the Wayfarer Restaurant & Lounge in Cannon Beach, Oregon}

September 21, 2020 – Willamette Valley Wine Tastings

We took advantage of our early wake time to walk along Cannon Beach during low tide. If you ever get the chance to do this, I highly recommend it. It is such a unique experience to explore the area as the water retreats to reveal an expansive beach dotted with intertidal pools. You’re also able to walk directly up to Haystack Rock or over to Crescent Beach and see all of the star fish and anemones that cling to the exposed rocks. We enjoyed exploring the near empty beach while we searched for sand dollars and enjoyed the incredible views.

We stopped briefly back in the hotel to change and load up our bags before checking-out. We grabbed coffee and a light breakfast from Sleepy Monk Coffee Roasters and then hit the road to Willamette Valley [drive took about 1 hour and 30 minutes].

We drove directly to our first tasting at Penner-Ash Wine Cellars. They were in the midst of harvest when we arrived which was exciting to watch from our vantage point on the patio over looking the vineyards. This was one of my favorite tasting experiences of the trip, both ambiance and wine. They were quite generous with their tasting and bonus pours. In total, we tasted nine wines – two Chardonnays and seven Pinot Noirs. We ended up taking home a bottle of the 2017 Zena Crown Pinot Noir and 2018 Shea Vineyard Pinot Noir.

Our second stop was a much smaller operation, Soter Vineyards at Mineral Springs Ranch. This biodynamic farm and vineyard “relies on the cycles of nature and regenerative agriculture to create a closed-loop system of biodiversity and self-sustaining ecology.” Soter Vineyards does not use synthetic fungicides, herbicides, or fertilizers instead favoring only holistic methods to improve soil health and combat common vineyards pests. Our tasting here took place in a small, private cabin overlooking the property which we learned previously functioned as the Soter’s children’s bedroom.

The final stop of our first day in Willamette Valley, and Kevin’s favorite, was Lenné Estate. Our tasting experience here was much more casual than the previous two which allowed us to explore the property a bit more and even taste some of the harvest. The views of the vineyard and surrounding areas is incredible from every angle and the Pinot Noir was delicious. The tasting room manager, Eric, is very friendly and knowledgable about the wines, history and Willamette Valley region.

All three wineries that we visited were in the Yamhill-Carlton AVA. We purposely grouped our tastings by AVA to maximize our days and reduce driving time. Since we visited during COVID, most wineries required reservations to visit although none of them were busy on the Monday we were there.

After checking in to The Allison Inn and Spa, we went straight to the pool to relax. Sadly, the spa was still closed [because of new COVID precautions] but we enjoyed the beautiful indoor hot tub and pool. That night for dinner, we went to Rosmarino Osteria Italiana in downtown Newberg. This place has rave reviews and certainly lived up to its reputation. The restaurant practices appropriate social distance guidelines and seated us outside on the patio. The service is great and the owner frequently stops by to chat and ask after your wine/food. Kevin and I both ordered pasta which is made fresh daily and it was so delicious. We really enjoyed our experience here and highly recommend it!

{Indoor poor at The Allison Inn & Spa}
{Dinner at Rosmarino Osteria Italiana in Newberg, Oregon}

September 22, 2020 – Willamette Valley Wine Tastings [Our Wedding Anniversary]

Our second wedding anniversary started with breakfast at Red Hills Market in Dundee. This cute restaurant and farm gift shop is the perfect place for a quick breakfast or lunch in Willamette Valley. Everything we tried was delicious and I would have loved to have gone back for lunch too if we had more time. After breakfast, we relaxed at the pool for a bit until our first tasting.

{Breakfast at Red Hills Market In Dundee, Oregon}

Our second day in Willamette Valley, we explored the Dundee Hills AVA. Our first stop, and my favorite of the trip, was Domaine Serene. We had beautiful weather and the most gorgeous view of the Evenstad Vineyard from our table. We started our tasting with a bonus pour of Sparkling to celebrate our anniversary and then went on to try another seven wines. All of them incredible and we especially loved their award winning Reserve Pinot Noir.

From here, we went directly across the street to Domaine Drouhin. This French family run vineyard has deep roots in the Burgundy region of France and brings that style of winemaking to Oregon. We really enjoyed our tasting experience here as it feels very curated. We visited in the midst of harvest so the vineyard was a hive of activity but the tasting area was very relaxing. In addition to their standard tasting flight, we got to sample freshly picked grapes from the harvest and a few Burgundian wines.

The last stop of the day and the trip was Stoller Family Estate. I was really looking forward to this tasting but we were both pretty disappointed. This winery was by far the most crowded of the six we visited and the tasting experience was quite impersonal. It seemed pretty commercialized and more of a ‘churn and burn’ type operation, as Kevin would say. I will say we enjoyed the wines and charcuterie board that we ordered but Stoller probably wouldn’t be on my list to revisit any time soon.

After our last tasting, we made our way back to hotel to relax before dinner. We had reservations at Jory Restaurant located inside our hotel. I’m always a bit wary of fancy hotel restaurants because they’re usually over priced and generic but I was really impressed by Jory. The seasonal menu features farm to table food, much of it grown onsite in the chef’s garden. We loved everything we tried and at the end, they surprised us with anniversary chocolates. It was the perfect way to end our anniversary and trip to Oregon.

The following morning, we drove back to Portland [about 50 mins] and flew home to our baby girl!

Accommodations & State Specific Details

Portland Stay: Canopy by Hilton Hotel Pearl District

Considering this is a four star hotel, I was a bit underwhelmed by the service, ambiance and room amenities. I realize hotel stays are different during COVID times but even during normal times, it felt more like a standard Hilton than anything special. That said, the room was clean and located within walking distance to everything in the Pearl District.

Cannon Beach Stay: Cannon Beach Hotel Lodgings

We booked this hotel last minute via the HotelTonight app and it wasn’t exactly what we were expecting based on the pictures in the app. Apparently Cannon Beach Hotel Lodgings has several properties within Cannon Beach in addition to their feature Boutique property. Technically, we stayed in the Hearthstone Inn which has more of rustic vibe and comes equipped with a small kitchenette and fireplace. While the room felt a bit outdated, it was cozy and well located in the middle of town, only a quick walk to the beach or all the restaurants/shops.

Willamette Valley Stay: The Allison Inn & Spa

We enjoyed our stay at The Allison Inn & Spa despite the changes made to accommodate COVID regulations. While we enjoyed the indoor pool area I was bummed that the spa was only open on the weekends. Service seemed good but was certainly limited at this time. I loved our room which had a sitting area, fireplace and small outdoor deck. We also really loved the Jory Restaurant as I mentioned above. The hotel is in the heart of Willamette Valley which makes it a great home base to explore the area – wineries and town alike.


To Oregon: We flew United from Chicago ORD to Portland PDX. Both of our flights were quite busy and we had to make a few strategic moves to avoid sitting directly next to a stranger on the plane.

Around Oregon: We rented a car from PDX and drove everywhere.

Currency: US Dollar (USD)

Language: English.

Outlet Adapter: The standard voltage is 120 V. The standard frequency is 60 Hz. The power sockets that are used are of type A and B. Standard United States adapters.

Passport/Visa Requirements: No U.S. Passport required.

Vaccinations/Medicines: N/A

Weather: Leading up to the trip, Oregon was experiencing terrible wildfires and the air quality was quite poor. It was looking like we may have to cancel but they ended up getting a rain shower the day before we were scheduled to leave that pushed the smoke out. By the time we landed, the weather was ideal for the Pacific Northwest in September. Mid-70’s in Portland and Willamette Valley and mid-60’s in Cannon Beach. Cool, damp mornings, partially sunny days and one brief rain shower while we were in Portland. Definitely pack layers and consider the possibility of rain.

One thought on “Oregon Itinerary – Portland, Cannon Beach & Willamette Valley

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s