How to Spend 72 Hours in Portland, Oregon

My favorite spots to eat, see, and shop
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72 Hours in Portland_Map

When I found out that Brooke, one of my best friends in L.A., got a new job and would be relocating to Portland, I was devastated. She's like family and I hated the idea of not getting to see her on a weekly basis. Luckily, we've been able to see each other three times since she moved a few months ago, but always in L.A. This past weekend, I finally got to visit her for an indulgent girls trip in which we hit up some of the best spots in and around the city. Read on for how we spent 72 hours together in Portland—and the spots I can't wait to re-visit:

72 Hours in Portland_Thursday
Brunch at Proud Mary

Brunch at Proud Mary

10:15 a.m. Grab brunch at a hip, Aussie-style cafe: As soon as I landed, we made our way to Proud Mary, an industrial space with friendly service and good food. Since I hadn't eaten anything since my alarm sounded at 4 a.m. to catch my flight, I opted for the Potato Hash—a massive portion with smoked bacon, a poached egg and kale salad (plus a Flat White). I got through about half of the dish before I got full, making it an ideal item to split.

12:00 p.m. Walk around NW 23rd Street: We drove to NW 23rd Street, a cute area with lots of shops. My favorite was Child's Play, an old-school shop that reminded me of the toy stores I went to as a kid. I bought Sloan a little pedicure set since she's always trying to steal my tools anytime I paint my toenails (spoiler: she loved it). 

Chicken and rice at Nong's Khao Man Gai

Chicken and rice at Nong's Khao Man Gai

72 Hours in Portland_TOP PICK

2:15 p.m. Go to The Pearl for an in-between meal: Even though we weren't exactly hungry, we had limited time to squeeze in all of the food on our must-eat list and Nong's Khao Man Gai* was at the top. We debated splitting a plate of chicken over rice with their incredible sauce (which is available at some specialty stores in L.A., including Cookbook), but made a game-time decision to get our own, which was the right move. I can't even describe what exactly made such a simple plate so good, but we ate quickly and in silence, before finishing the meal with some of their palate-cleansing broth.

Note: I've denoted my favorite spots with an *

Chocolate-dipped soft serve at Wiz Bang Bar (wearing a Cupcakes and Cashmere silk trench, available soon!)

Chocolate-dipped soft serve at Wiz Bang Bar (wearing a Cupcakes and Cashmere silk trench, available soon!)

3:00 p.m. Head towards Old Town for dessert: About a week before my trip, Brooke tagged me in an Instagram of Wiz Bang Bar, Salt and Straw's soft serve dessert bar, knowing it would be right up my alley. So naturally after our already decadent morning, we squeezed in a stop where I got a vanilla custard soft serve dipped in their single-origin chocolate shell. It provided just enough energy for a multi-hour walking tour of some of the best shopping in Portland.

72 Hours in Portland_TOP PICK

3:30 p.m - 6:00 p.m. Shop the best boutiques in the city: One of our favorite strategies in discovering good places to shop (after all, Brooke only became a local recently) was to find one cute store and ask the salesperson for her go-to places. We heard a lot of the same spots: WM Goods (flowy basics plus some cool beauty products), Alder & Co (beautiful floral arrangements + a curated beauty selection), Frances May* (my personal favorite with pieces by Rejina Pyo, Ulla Johnson, Maryam Nassir Zadeh, Rachel Comey, and Jesse Kamm), Spartan* (the chicest home store that will make you want to move in and/or redo your own place), and Maak Lab (a small shop that makes their own soaps, perfumes and candles, of which they make signature scents for some of the coolest restaurants in town, like Ava Gene's and Tusk). After our afternoon of shopping, we headed back to Brooke's place and took her dog Jack for a long walk to the Portland Rose Garden. We dropped him back off, washed up, and got ready for a late dinner.

72 Hours in Portland_TOP PICK

8:30 p.m. Grab a seat at the bar of a busy restaurant for dinner: One of the most appealing parts about being in Portland is that people are very casual when it comes to what they wear. While I had the best of intentions of wearing one of the cute summery dresses I'd packed (the weather hovered around 80 degrees the entire time and was flawless), I ended up in a sweatshirt and running shoes and totally fit in. We decided on Canard*, the more casual sister restaurant of Le Pigeon, with a beautiful space and a great bar. We got ice-cold glasses of wine, which paired perfectly with our rather impressive dinner: heirloom tomatoes, a steam burger, chicken wings with truffle ranch, chips and dip with smoked mackerel, pancakes with duck gravy, and their butterscotch chocolate pie. 

72 Hours in Portland_FRIDAY
Berry picking at Columbia Farms on Sauvie Island

Berry picking at Columbia Farms on Sauvie Island

10:00 a.m. - 12:00 p.m. Cross the bridge in search of berries: After a leisurely morning spent at home with coffee, we headed out to Sauvie Island to go berry picking. We visited Columbia Farms, where we purchased boxes and headed out to the fields to pick different varietals of blueberries, raspberries, and boysenberries. We took our time navigating each aisle, chatting to the sound of birds chirping with the wind in our hair. We ate warm berries off the vine and each filled two flats to the brim (for $17) before heading out to lunch.

Guacamole and chips at Guero No. 1 Tortas

Guacamole and chips at Guero No. 1 Tortas

72 Hours in Portland_TOP PICK

12:25 p.m. - Seek out the best torta in the city: We worked up quite an appetite after skipping breakfast in lieu of berries, so by the time we arrived at Guero No. 1 Tortas*, we were famished. We opted for their refreshing melon and avocado salad (note to self: try and replicate at home immediately), guacamole and chips, torta with beef, fried egg, cotija, and pickled jalapeños, and Mexican corn.

3:00 p.m. - 7:00 p.m. Head home to nap and then reorganize your friend's bookshelves: At least this is what I did...

Ava Gene's

Ava Gene's

72 Hours in Portland_TOP PICK

7:30 p.m. - Put your name in for one of the hottest restaurants in town, then prepare to wait a bit: I received about two dozen recommendations for Ava Gene's*, so despite the hour-long estimated wait, we were happy to walk around SE Division Street to look in the shop windows and check out the other restaurants and bars. They texted us after about 45 minutes and we got a little table outside on the street (side note: the marble slab upon which I was seated could have benefited greatly from a cushion). Everything we ordered was "aggressively seasonal" and bursting with flavor: cold grilled artichokes with salted brown butter, sheep cheese and cherry tomatoes on grilled bread, green beans with radishes and almonds, a little gem caesar, and house-made tagliatelle with bolognese. We'd intended to walk down the street to get frozen yogurt at Eb & Bean, but by the time we left at 11:30 p.m., we were ready for bed.

72 Hours in Portland_SATURDAY
Ethiopian varietals at Heart 

Ethiopian varietals at Heart 

72 Hours in Portland_TOP PICK

9:00 a.m. - Hit up the best coffee roaster in the city: I know I'm biased, but G and I have been drinking Heart Coffee*, a Portland staple, for years and it was the single best espresso drink I've had in the US (my all-time favorite was in Kyoto). We buy it in bulk from shops in L.A., and as soon as I heard there were several locations around Portland, I couldn't wait to try it in person. We went to the one in The Pearl, which was gorgeously understated and boasted the hippest clientele in the city. I beelined to their selection of bagged coffees and promptly bought four bags of their different Ethiopian varieties to bring home. While there, I ordered my usual, a Flat White, and loved it so much that I debated ordering a second on the spot (which is never a good idea for someone as highly affected by caffeine as myself)

Hike by Pittock Mansion

Hike by Pittock Mansion

10:00 a.m. - Get out in nature for an easy hike: I'm embarrassed to admit that I'm not big into exercising out in nature unless the path is both quick and easy. In the case of the hike up to Pittock Mansion (which took about 30-45 minutes, round-trip), it was exactly what we were looking for and wound through a lush forest that was more or less deserted. The top of the trail ended at a century-old mansion that offered gorgeous views of the entire city. 

Grain bowl at Tusk

Grain bowl at Tusk

72 Hours in Portland_TOP PICK

12:00 p.m. - Go out for a brunch you'll never stop thinking about: After our hike, and still in our yoga pants, we went to brunch at Tusk.* It's has a Mediterranean-inspired menu and the hummus with their house-made flat bread was the best I've ever had. We also got the marinated feta, romaine salad, grain bowl with egg, and two cocktails. I had the Bloody Mary, which hit the spot, but it was Brooke's "Diving Bell," with gin, pisco, matcha, and orange blossom cream, that was the sleeper hit. We left absolutely satiated, without feeling deliriously full, which had been kind of the norm throughout our trip. We took about an hour-long walk alongside East Burnside, ducking in and out of several boutiques along the way.

Vanilla rose boba tea

Vanilla rose boba tea

3:00 p.m. - Grab a boba tea on a hot afternoon: By the time we'd logged in a couple of miles, we were hot and exhausted, so we stopped into Tea Bar. I'm not the biggest fan of tea in general, but was pleasantly surprised by the very refreshing vanilla rose boba tea I ordered. 

4:00 p.m. - 7:00 p.m. - Take long naps and online shop with your friend for her new house. 

72 Hours in Portland_TOP PICK

8:00 p.m. - Go to a whiskey bar that feels straight out of Hogwarts. I'm a big whiskey fan, but only in cooler months, so when we decided to go to Multnomah Whiskey Library*, I was skeptical whether I'd find a cocktail that appealed to me in July. Needless to say, their selection was the most impressive I'd ever seen and the location felt like a magical secret society. They take walk-ins, but since it tends to get busy, you're also able to buy a "Hall Pass" to guarantee a reservation at least 48 hours in advance. I ordered a gin martini and then a Bee's Knees, both of which were excellently crafted and paired nicely with our cheese plate, charcuterie board, and house-made sourdough bread with butter. After we saw another table enjoying a large bowl of popcorn (that was nowhere to be found on their expansive menu), we asked our bartender about it, who informed us that their three flavors of artisanal popcorn were one of their off-menu items. We chose the pecorino option, which was perhaps the highlight of the entire night.

72 Hours in Portland_SUNDAY

7:30 a.m. - Squeeze in one last stop for coffee at an institution: After I'd shared my trip to Heart, several readers insisted I stop at Coava (pronounced "Cove-uh," which I mispronounced) before I left. I thought it was a very good Flat White (I like to stick to one type of drink throughout a stay to ensure I judge each spot based on the same criteria), but not as good as Heart. It did make for a sweet final stop, en route to the airport, in what turned out to be a rather epic food tour of Portland.