5 Days in Portland and the Willamette Valley

Oct 9, 2023 | Travel

The Willamette Valley is dubbed “the new Napa” – and there’s good reason to choose the Pacific Northwest for a wine-sipping holiday.

Why I Went: Wine tasting, of course! After our honeymoon to Australia, where we got to taste our way through the Yarra Valley and Mornington Peninsula, we were eager to spend another few days in a top wine region.

What I was Surprised By: Firstly, before you go, you better know that it’s pronounced “will-AM-it” not “willa-met”. You can easily remember it by the phrase: “Will-AM-it, dammit”. Secondly, the sheer number of wineries (700!) in the Willamette Valley and the amount of investment that has gone into the construction of some of the buildings is incredible. You get a beautiful mix of small operators, with the architecture of big players. Despite the investment in wineries, there are few hotels and restaurants (but I’ll tell you about the great ones in this post!). And finally, the people are incredibly kind (truly – this is coming from a Canadian!).

Who It’s Great For:

  • Solo travel
  • Couples
  • Foodies!


If it has a ✨ emoji beside it, that means I went there myself. Everything else was on my well-researched ‘must-hit’ list when planning, but alas, I couldn’t go everywhere!

If there’s a 🤍 emoji beside it, that means I loved this spot and would return.

If there’s a 🌼 emoji beside it, that means it’s worth going once, but I likely wouldn’t return if you’ve already been (or if you’re hesitant about it anyway).

I don’t share anything on Middle of Somewhere that I personally wouldn’t recommend going to.

Why You Should Go

Victorian Homes Charleston

World Class Wine

…especially Pinot Noirs

💡 Did you know? The Willamette Valley is on the same latitude as Burgundy, and has similar climate for growing grapes. You’ll largely be drinking Pinot Noirs, with a sprinkling of Chardonnay and other varietals like Viognier. 


farm-to-table dinners, unique pizza toppings, thai meets BBQ and more

💡 Portland and the Willamette Valley are renowned for farm-to-table dining, and exceptional culinary diversity. You’ll often find chefs leveraging unique combinations of ingredients to make familiar dishes just that little bit more ‘wow’ – like unfamiliar toppings on pizza, the absolute sweetest corn in your pasta or brisket burnt ends in your Thai curry.

Portland is also known for a robust food truck scene with plenty of food truck pods dotting the city. Here, you can expect to see an elevated food truck experience, with elevated tables, covered areas and fire pits.

Close Proximity

You can get from the city to the wine valley in a mere 45 minutes

The proximity of the Willamette Valley to Portland offers an amazing opportunity for city dwellers (or in-and-out travellers) to escape into a picturesque wine country, experiencing world-class vineyards and breathtaking landscapes just a short drive away.

Robust Coffee Scene

Independent coffee shops galore

Portland’s coffee scene is a caffeinated haven, where artisanal coffee shops dot every neighbourhood, each with its unique blend and atmosphere. Locals and visitors alike revel in the city’s commitment to quality, savouring meticulously brewed single-origin beans and creative espresso concoctions. From cozy, hole-in-the-wall roasters to bustling, community-centric cafes, Portland’s coffee culture thrives as a testament to the city’s dedication to the perfect cup.


Below are a round-up of my favourite places & experiences. Keep scrolling to find more recommendations on where to eat & drink, what to do and where to wander, plus a full itinerary.

1. Private Tasting at Abbott Claim

One of our favourite tastings in Willamette Valley was at Abbot Claim. Available by appointment only, with the tasting culminating in their barrel room, this was a pretty spectacular experience.

2. Antica Terra Tasting Experience

Another incredible tasting experience was at Antica Terra. The tasting involved a contrast to some of the best bottles of French and Spanish wine, so you could get an idea for how great Antica Terra’s wines are.

3. Inn the Ground

Inn The Ground opened only a month before our arrival, and it’s the perfect combination of an elevated stay, striking architecture, farm-to-table breakfast, and beautiful trails and views across the Pacific Northwest.

4. Dinner at Eem

Dinner at Eem typically comes with a 1+ hour wait, for good reason. They combine Thai with Southern BBQ – a unique combination that feels so much like the essence of Portland. I would return here in a heartbeat.

5. International Rose Test Garden

The International Rose Test Garden includes over 10,000 roses, including over 600 varieties, perched at the top of a hill. The flowers are in bloom from late May to October and it’s a spectacular site.

Bonus: Coffee Scene

A bonus pick from Dave (since I don’t drink coffee) is the bustling coffee scene in Portland. Stumptown stood out as his favourite.

Abbot Claim Winery Oregon
Inn the Ground Breakfast

Inn the Ground Breakfast


Oregon is an exceptional culinary destination, celebrated for, locally farmed ingredients, top-tier hospitality professionals and the pioneering spirit that continuously pushes the boundaries of culinary creativity.

Below are the best places to eat in Portland and the Willamette Valley.

Eem Portland

Eem | Eem is a true Portland gem that creatively fuses Thai and Texas barbecue to create a unique, and memorable dinner out. Here, you’ll find innovative dishes like white curry with brisket smoked ends and “very spicy” papaya salad. Their pad kra pao is made with crispy pork belly, and left me thinking about it for weeks. If you love Thai and BBQ, Eem is a must-visit.✨🤍

Lovely's Fifty Fifty

Lovely’s Fifty Fifty | Where ice cream and pizza meets unique flavour combinations. Lovely’s Fifty Fifty gained a robust following after being in the spotlight on Netflix’s Chef’s Table – Pizza. She spent five years making bread daily, eventually leveraging that knowledge to perfect pizza crust. You won’t find that familiar tomato base on her pies; instead, you’ll discover her favourite finds from local farmers markets – from concord grapes to shishito peppers, peaches and corn. It’s a must-visit for those interested in discovering a fresh and innovative way to enjoy pizza. ✨🤍

Sokol Blosser Farm and Forage Lunch

Sokol Blosser Farm and Forage Lunch | If you’re looking for a winery lunch in Willamette Valley, you’ll be limited on options. While there are plenty of places to enjoy a charcuterie board, and several more that allow you to bring a picnic, not many offer an elevated lunch experience. The Sokol Blosser Farm and Forage lunch experience highlights the region’s seasonal bounty, with ingredients sourced directly from the estate’s organic gardens and local farmers – sometimes foraged by the chef himself. The lunch is paired with wines from Sokol Blosser winery. While we really enjoyed the food, company and views at this winery, there were a few things we were longing for:

  • The dining room, while private, felt like it was missing the architectural awe that other areas of the property had. We would’ve loved to be in the main room with the stunning wood detail on the vaulted ceiling, or on the side porch with panoramic views. Instead, the room we were in felt a bit like a dated fishbowl.
  • While the chef described the food wonderfully, we felt there could have been more storytelling with the wine pairings. They lacked explanation of why the pairings were made, and could’ve highlighted notes that we should have tasted as we flipped from wine sips to food bites.
  • The building and views are beautiful, but unfortunately they set the car park right in front of the building, so to enjoy the view, you need to look over a sea of vehicles first.


Humble Spirit McMinnville Oregon

Humble Spirit | Humble Spirit is THE place to dine in McMinnville. With a farm-to-table focus (the owners also run their own a farm!), you know you’re getting exceptional quality. That, paired with a creative but anchored chef, means that you’ll want to savour each bite. We dined on Oregon Bay shrimp rolls, a delightful burger (their fries are so good!!!), a corn pasta and beet salad. ✨🤍

Red Hills Market

Red Hills Market | Red Hills Market is a perfect spot to grab lunch, or charcuterie ingredients for a winery picnic or hotel dinner. Located in Dundee, it’s nestled right in the middle of wine region. We went back multiple times throughout our trip – they make pizzas and sandwiches to-order (we had their famous roast beef and it was delightful). They also have a lovely wine selection and other items that are perfect for gifts – like local olive oils and other condiments. ✨🤍

Hawthorne Asylum Food Truck Pod Portland

Food Truck Pods

Portland is known for their food truck scene, so it would be shame to visit without checking out one (or a few!). Here are some that we visited:

  • Nob Hill Food Carts | This is a small truck tucked behind NW 23rd (so perfect to visit while strolling that street). They have ~6 trucks and a couple of picnic tables. We opted for a smashburger from Farmer and the Beast and it was delicious (though I’d opt for more patty’s next time – they’re quite thin). ✨🤍
  • Hawthorne Asylum | This food pod is on the east side, and naturally (given the name) tucked behind a concrete wall and barbed wire. Inside, you’ll find a great setup of nice picnic tables, covered areas, washrooms and even a long fire. We indulged in a Korean burrito with spicy pork and it was great! ✨🌼
  • Cartopia | Just around the corner from Hawthorne, this spot has fewer trucks but an arguably cuter vibe. Since we just ate, we didn’t grab anything here, but the thai spot, fried chicken and pizza places all looked great. ✨🤍
Blue Star Donuts

Desserts! It seemed like Portland has a dessert spot around every corner.

Blue Star Donuts | We tried a couple donut shops, and this was by far the best. We indulged in four (yes, woops) including: blueberry bourbon, apple fritter, lemon lime custard, and old fashioned. They were divine. ✨🤍

Salt and Straw | No better place to get handmade ice cream than Salt and Straw. There are a few locations around Portland and it’s certainly worth a visit (yes, even if that means eating it ~1 hour after your donut indulgence, like we did). Their ice cream is homemade and they – like many spots in Portland – use a unique spin on ingredients you wouldn’t typically find in ice cream. Opt for a fun flavour like their pear and blue cheese or strawberry balsamic.✨🤍

Rosmarino Oregon

Here are a few other spots that we went to but didn’t love quite as much:

  • Carlton Bakery: This place is cute (and a great spot for a bathroom break), but we found their pastries overpriced and only OK (and I pretty much stop in every bakery I go by, so I have a good radar for this kind of thing!). I’d only pop in to grab a coffee and cheese and meats to go (though the selection is small). ✨🌼
  • Rosmarino Osteria Italiana: Perhaps we’re spoiled for choice in Toronto and on all of our travels, but this spot just didn’t live up to the extremely high ratings for us. I enjoyed my short rib pasta, but the arribata pasta tasted off – sadly that fake chemically taste (and was not spicy). We unfortunately left feeling pretty meh about it overall. ✨🌼
Kann Portland

And some additional restaurants that were at the top of my list, but unfortunately didn’t have time to go to (or couldn’t snag a reservation):

In Portland:

  • Kann | I wanted to go here very badly, but unfortunately there were no reservations. I even added myself to the waitlist with no avail. It has hailed extremely good ratings and is described as “Haitian cuisine meets Pacific Northwest bounty at kann, a live-fire restaurant from James Beard Award Winning chef Gregory Gourdet.”
  • Canard | They have a great $2 oyster Happy Hour from 4-5pm Monday-Thursday.
  • Jacqueline | Another highly rated oyster bar (can you tell I love oysters?)
  • Le Pigeon | A hot-spot French inspired restaurant, right next to Canard
  • Tusk | I went here the last time I visited Portland, and they served up delicious Middle Eastern food in a very cute, pink-hued room

McMinnville, Willamette Valley:

  • Okta | While we didn’t make it to Okta, I heard great things about this high-end McMinnville restaurant. At $285 a head, this 10-course tasting menu was a little out of our budget. They describe their menu as: “highlighting our hearth’s mimicking of the summer sun and its impact on flavor.” If you’re keen to visit, but it’s also above your budget, you can try tout their $195pp 5-6 course tasting menu instead.
  • Mac Market | We unfortunately didn’t get to go to Mac Market, as it was closed on the days we were visiting. But Hayward sounded like a great dinner spot, and Honey Pie a great spot for pizza. If you can’t make it for dinner then check out Bakery Bar in the morning for some baked goods.
Patricia Green Cellars

Patricia Green Cellars


And of course, what would the Willamette Valley be without wine. Below are a list of spots to enjoy a glass or a tasting! Some general tips:

  • Try to do a vertical tasting (i.e. tasting the same varietals, produced in different years – eg. 2018 vs 2019) or a horizontal tasting (i.e. same year, different wines).
  • Avoid 2020 wines (they were sadly impacted by the wildfires. Most places won’t even serve these, but some try to quietly still sell tastings, glasses or bottles of 2020 wines.)
  • Be safe! Don’t drink and drive. Here are your options: hire a driver, spread your trip our over more days, or opt for single tastings (with a DD) or share tastings
Abbot Claim Portland

Abbot Claim: Visiting Abbot Claim was one of the highlights of our trip. We happened to have a private tasting. The architect was incredibly thoughtful in the design and we loved hearing about every aspect – like the narrow windows that were specifically designed to face the sun, allowing gentle sunlight into the manufacturing area.

They intended to build a tasting room, but plans got put on hold due to COVID. That meant that Bri, our host, had to come up with a creative solution to holding tastings. In retrospect, this resulted in the most impeccable wine tasting experience. We met her at the end of the driveway and were welcomed with bubbly and an explanation (with a sample) of their soil. From there, we ventured inside for another glass of wine (already set up and waiting for us), and got to witness the post-harvest activities in action. Then, we went through beautifully hand-made doors made from wood from the ceiling of a monastery (built by a friend of theirs who works at Nike and started their own woodworking business) into their wine barrel room. A stunning curved hallway filled with barrels led us to a candle-lit table where we would conduct the rest of our tastings. Accompanying the wine were small bites of Serrano ham, manchego cheese and caviar. Truly a spectacular experience and worth every penny. ✨🤍

Antica Terra Oregon

Antica Terra: The tasting experience at Antica Terra was unique for two reasons. First, they paired the tasting with delicious bites of local products – from locally farmed crudité, smoked sablefish and rabbit liver pate. If you’re not a foodie, this might feel a little ‘fussy’, but for us it was delicious. Second, they had you taste world-class wines (truly, they had $250 bottles of French and Spanish wines in the line up) to compare it to their wine, so you could better understand the quality of wine they’re making at Antica Terra. They recently moved to a new property, with the tasting taking place in a large warehouse; the experience ended up being a unique combination industrial and intimate. ✨🤍

Lingua Franca Oregon

Lingua Franca: Chosen to mean “universal language”, they named Lingua Franca to represent how wine can bring people together – no matter the background. They’ve gained recognition for its commitment to producing top-tier Pinot Noir and Chardonnay wines. Founded by renowned sommelier Larry Stone and notable Burgundian winemaker Dominique Lafon, the winery has made a name for itself by meticulously crafting wines that capture the terroir of the Eola-Amity Hills region, earning praise from wine enthusiasts and critics alike. They also arguably have some of the coolest wine labels in the region, showcasing a local artisan. ✨🤍

Penner-Ash Oregon

Penner-Ash: Arguably, some of our favourite wines priced under $100/bottle. They focus on fuller-bodied Pinots, which is more our speed (we’re partial to a Cab), so we particularly enjoyed these. The tasting room is also beautiful – centred around a large floor-to-ceiling fireplace, looking over the manufacturing area, and out onto sweeping views of the valley. I would return here time and time again. ✨🤍

Dominio IV Oregon

The above were our favourite wineries, but we also went to a few more:

  • Rex Hill: Solid wines, nice modern buildings with a beautiful patio. Limited views and we felt the servers were sub-par. It’s the most commercial winery we went to, with their neighbouring A to Z brand (available in Ontario LCBOs), although Rex Hill is their higher end label. ✨🌼
  • Cristom: This winery is quaint, with a little patio overlooking valleys. We particularly enjoyed the viognier (took a bottle home with us to enjoy at our hotel that evening), but overall it wasn’t quite as standout as some of the other spots.✨🌼
  • Dominio IV: This was the smallest winery we went to. It was set in a cute old farmhouse, and we learned so many stories about the founders travels and creativity. Don’t miss an explanation of their Imagination Series wine labels, drawn by the founder as as his expression of how he sees the wine, in shapes and colours, when he tastes it. ✨🌼
  • Patricia Green Cellars: Another smaller scale producer – they serve your tasting with delicious cheese, overlooking a beautiful flower garden and their vineyards (Pictured above). This was our last stop, so perhaps it was feeling a bit repetitive at this point, but despite Reddit singing Patricia Green’s praises, there wasn’t anything overly standout to us. ✨🌼
The Box Social Portland

The Box Social: When you head to Eem, you’re likely going to end up on a waitlist (we had to wait 1 hour and 45 mins!!), and you’ll be looking for a place to enjoy a drink before dinner. Head down the street to The Box Social for some elevated cocktails in an intimate environment. Dave particularly enjoyed the pickle martini, but they have everything from dark boozy cocktails to tropical mixes. ✨🤍

Stumptown Coffee Portland

Portland is known for coffee. Here’s where we ventured to…

  • Stumptown (Dave’s favourite): Founded in 1999, Stumptown has played a significant part in elevating Portland’s reputation as a coffee destination. You’ll find many throughout the city but the one on SW 3rd is quite aesthetic. ✨🤍
  • 40lbs: Downtown  in a cool industrial space, nestled into downtown ✨🤍
  • Venster Coffee: A very tiny coffee shop. Dave found it a little more bitter, but worth going for just the unique nature of how tiny this spot is.✨🌼

We also enjoyed an awesome tea tasting experience at Smith Teamaker in an industrial area on Washington St (on the east side of Portland). You get to smell all of the tea leaves and then select a few for a tasting flight. We enjoyed it on their outdoor patio, but inside you can see the team at work behind the scenes (there’s a large window overlooking the production area).

Wayfinder Brewing

There are a lot of breweries in Portland, so naturally we had to check out a few.

Portland Oregon Hikes

Portland forest on the way to the International Rose Test Garden


While our trip was heavily focused on exploring wineries in the Willamette Valley, we carved out two days to explore Portland. It’s a walkable city (yes, even going over the bridge to explore from east to west is easy!), and so I recommend exploring on foot. Here are the best things to check out while you’re in town!

International Rose Test Garden

International Rose Test Garden: The first time I travelled to Portland was in January, so I missed out on the roses being in bloom. I was eager to check out the garden once more, this time in October. It’s a true botanical haven, including over 10,000 rose bushes representing more than 650 varieties of roses. Established in 1917, it now serves as a test ground for new rose cultivars, and what gives Portland the name ‘City of Roses’. It originally came to be when Jesse A. Currey, a rose hobbyist and Sunday editor of the Oregon Journal, convinced city officials to start a rose garden to serve as a way to protect hybrid roses grown in Europe during World War I. Roses bloom from late May to October depending on the weather. ✨🤍

Salt and Straw Ice Cream

Wandering NW 23rd Avenue: While downtown has unfortunately become filled with homeless camp and rampant drug use (though worth noting that we never felt unsafe), NW 23rd Avenue was a beautiful change of pace. With a mix of restaurants and shops, it’s a great little strip to spend an hour or so wandering. Be sure to pop into a local brewery (like Breakside Brewing). You can also easily access the park that leads to the International Rose Test Garden from the south end of 23rd. ✨🤍

Inn the Ground Oregon Hotel

Inn The Ground Stay and Hike: We happened to discover Inn The Ground as we were last-minute planning for our trip, and we’re so glad we found it. It had only been open for just over a month, and boy was it spectacular. The building is literally built into the ground, looking out across a beautiful valley that fills with fog in the morning. We were greeted with warm cookies and a warm fire upon arrival. Then, it was peace and quiet, as the staff retreated for the evening and we sipped wine by the fire. Our room was expansive, and we woke up to the sunrise and shapeshifting fog as we stared out in awe across the valley. For breakfast, we were served farm raised eggs and ham, accompanied by a green juice and the best bread and butter one could dream of at 8AM. We also had a lovely chat with the owner. After breakfast, we took to their trails, and spent over an hour wandering up and down through their fields and forests, taking in the beauty of the Pacific Northwest. Alternatively, we could’ve opted to play pickleball in their sports facility down the road, but we were drawn to the outdoors on this trip. I cannot recommend this stay enough. Once we checked out, it was off to the nearby wineries for some tastings. ✨🤍


Since I know not everyone is a planner, I’ve done the hard part for you so that you can just pack your bags and enjoy 🧳 ✈️ 👟.
Travel Portland

Day 1: Portland

Assuming you arrived the evening before, you have a full day of exploration ahead of you.

☕️ Start by enjoying a coffee at Stumptown.

🧺 If you’re visiting on the weekend, check out the Portland Saturday Market, which despite the name, actually takes place on both Saturday and Sunday (transparently, we didn’t love this, but it’s a popular attraction. It’s mostly artisans, with a few food stalls). Instead, you could opt to head to brunch (we wanted to save room for donuts, so skipped breakfast).

👟 Wander around downtown and the Pearl District. Be sure to check out Powell City Books (it’s the largest independent bookstore in the world, making up an entire block!). The surrounding neighbourhood has a collection of nice shops. Made Here is worth checking out for artisanal goods made in Portland.

🍩 Grab a donut (or four) at Blue Star Donuts. The original donut hotspot is Voodoo, but Blue Star are said to be much better.

🌹 Walk up to the International Rose Test Garden (as long as you’re visiting between May – October). If you’re visiting outside of the in-bloom season, wander around the adjacent Portland Japanese Garden or take a longer hike up to the Witch’s Castle.

👟 Follow the path down from the International Rose Test Garden to NW 23rd. Continue meandering down NW 23rd to check out the shops. If you’re feeling up to it, grab an ice cream from Salt and Straw. Otherwise, check out a brewery, like Breakside Brewing for a local brew.

🥘 Put your name on the list at Eem (the wait is definitely worth it!) and wander down the street to The Box Social for a pre-dinner cocktail. Be sure to order the white curry with brisket burnt ends once you’re back at Eem!

Penner-Ash Winery Oregon


🚘 Rent a car and head 45mins – 1 hour south to the Willamette Valley. Most wineries require bookings in advance, and they’re often at fixed timeframes – eg. 10AM, 11:30AM, 1PM, 3PM (but will vary by the winery).

🍷 Head straight to your first winery (I recommend starting strong with a 10AM visit to Abbott Claim), and then tour your way through the valley. We did 3 wineries a day (I wouldn’t recommend more as the tastings are truly generally over 1 hour each). Be sure to have a designated driver! Our favourite spots: Abbott Claim, Antica Terra, Penner-Ash, and Lingua Franca.

🏨 Drop your bags at a hotel. We split our stay between two hotels: Atticus in McMinnville (so we could walk to dinner and not worry about more driving) and Inn The Ground (for a spectacular high-end boutique experience). Another great option is the Alison Inn and Spa (especially if you’re keen on a spa vacation).

🍝 If you’re in or near McMinnville, head to Humble Spirit for dinner. You can grab a rooftop cocktail at McMenamins Rooftop Bar or head to a wine tasting in-town (there are a few wineries with a tasting room on the main strip, and a couple other wine bars that highlight wines from the region and around the world. Hi-Fi came highly rated by some hospitality professionals in the area). Alternatively, go to Mac Market and check out Hayward Market. If you’re staying at the Alison, enjoy an elevated dinner at Jory.

🍷 Over the next couple of days, taste more wine and eat more food. Stop at Red Hills Market for lunch. If you’re looking for lunch at a winery, you can check out Sokol Blosser (see above for our review), Soter Vineyards, Furioso Vineyards (they often have a pizza truck on the property), Domaine Willamette, Brooks Wine, Willamette Valley Vineyards, or Rex Hill.

🍕Once back in Portland, grab dinner at Netflix’s famed Lovely’s Fifty Fifty for pizza with unique toppings. Alternatively, check out Canard, Kann, Jacqueline, Tusk, or Le Pigeon.

Wayfinder Brewery Portland


🫖 Head over to the east side to do a tea flight at Smith Teamaker on Washington. More of a coffee person? Literally open up Google Maps and search “coffee” – I promise you’ll find enough options!

🚛 Enjoy lunch at a food truck. Food truck pods are truly part of the culture in Portland, so you have to check at least one out before you leave. We loved Farmer and the Beast (for a burger), but since you’re on the east side check out Hawthorne Food Truck Pods and Cartopia (they’re a block apart, so you’ll surely find something you like). We enjoyed a Korean burrito from Hawthorne – they also have a firepit and nice seats (definitely more established than the food truck parks back home!)

👟 Get your steps in. Explore some of the neighbourhoods on the east side – I particularly liked this strip of SE Division St.

🥧 Pop into Lauretta Jean’s for a slice of heavenly pie. The banana cream pie was excellent, but you really can’t go wrong.

🍻 Grab a beer at any of the breweries on the west side. We took an Uber down to Wayfinder, which is back by the morning tea spot. They have a great patio and expansive indoor space – both perfect to sip on a cold one.

🏡 Head home

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