Diary of 72 Hours in Portland

We landed at noon on a Friday, ready to engulf ourselves in the culture of the liberal, hipster town of Portland. Home of beer, wine, a thriving food scene and plenty of outdoor activity. And we only had 72 hours in Portland. The weekend we landed in early May was the first sunshine-y day after many dreary, rainy weekends so everyone took to the streets and parks like a flash flood. The city was bumpin’.

First stop: Checking into our Air BnB in the newly gentrified area of Mississippi, an absolutely fantastically decorated one-bedroom garage apartment called The Arthaus. Three blocks to Mississippi Ave., definitely one of the coolest food/wine/beer/shopping districts in Portland. And cool it is. Nary anyone over 40 in these parts. Things to hit in this ‘hood include Blue Star Donuts (don’t get sucked into the Voodoo tourist trap), Ruby Jewel Ice Cream, Ink & Peat, Miss Delta Restaurant, and Fresh Pot (coffee, and not be confused with Nectar, the actual pot shop a few doors down).

Next up, we headed to the food carts (not trucks) in downtown Portland to explore the seriously endless options. These aren’t trucks with wheels that move like in most other cities, but more like stationary food vendors that semi-permanently take over parking lots. A group of three of them is called a “pod” and pretty much any business can host a pod if they want. Anywhere. There are, literally, hundreds of food carts spread throughout Portland and being at one of these gatherings is food nirvana, mostly due to the fierce competition. If your food sucks, people find out about it. Some that impressed me were: Nong’s Khao Man Gai, Dump Truck, and the Frying Scotman. There are SO many others. For the newest and brightest stars, Check out Portland’s Eater. 

Since we were downtown, we walked to the waterfront, where the water art displays blew my California-water-conservation mind away. The surrounding park is super cool and lush, where Portlanders walk their dogs, take a run and chill on weekend afternoons. From here, we walk across the bridge to The Rum Club, easily the coolest place we visited in Portland. Incredibly creative cocktails (even a daily special), solid upscale bar food and a very, very warm welcome. Just go.

Portlanders are super nice. But you will see plaid everywhere. And beards. Prepare yourself.

We hired a private tour guide for the first part of our second day. Yep, a private tour guide. Sounds pretty baller huh? If $65 per person is baller, then I’m in every time. We booked the tour on a whim through Trip Advisor. Sarah, a former Chamber of Commerce employee who knows her Portland digs and trivia, picked us up at our apartment in her personal car and launched a customized Portland tour for us, complete with a visit to a pot shop. A first time for me and it was surreal. Very knowledgeable people who man those pot counters… and it’s obvious they’re well versed with the product (even while working). There are multitudinous cannabis stores around Portland but they’re cash only so come prepared if you’re partaking.

Continuing our 72 hours in Portland awesomeness, we headed south that afternoon to Willamette Valley since no foodie trip to Portland is complete without a visit to Oregon wine country. You’ll drive 45 minutes to an hour before seeing vineyards but then you’ll see a lot of them. Glorious Pinot Noirs and Chardonnay. I had visited the region before but my husband had not so I booked a private tasting at an uber boutique winery called Big Table Farm, tucked away in the hills around Gaston. Owners Clare Carver and Brian Marcy are a husband and wife team who relocated to Willamette from Napa in 2006 and have been raising cattle, pigs, vegetables and making wine ever since. Their wines are gorgeous, inspired and lovingly crafted, complete with beautifully illustrated labels (Clare is an artist too). They make a refreshing, aromatic white Edelzwicker blend of Gewürztraminer, Riesling, Pinot Gris with a touch of Sylvaner that is almost indescribable in its uniqueness. Although I enjoyed their Pinot Noirs, Brian’s Chardonnays are simply elegant. I walked away with a mixed case of pretty much everything I tried.

The Saturday evening brought an exploration of the legendary Portland Pok Pok Thai restaurant. The original, main location in Portland, on SE Division, is packed all the time. Literally. So a tip from a friend turned us on to another, less hipster location called Pok Pok Noi. Gotta say, it was just OK. Greasy, and overly (and needlessly) spicy.  I ate at the original location a few years ago and remembered it being amazing but Pok Pok Noi was a letdown. But that could have been the night.

Like many hip cities, Sunday brunch is a “thing” in Portland. So the whole world packs into the limited number of restaurants that open for this eating phenomenon. We met up with some friends at Tasty and Alder in Mississippi as a party of 8 or so. We waited an hour. Why so long…? No reservations…

[Side note: I loved this city but they need to get with the restaurant reservations program. It’s really the only complaint I had against Portland – no restaurants take reservations. Must be the plaid/beard hipster set who sets these stupid rules. Maddening.]

Tasty and Alder – a name I’m sure came right off of the Hipster Business Name Generator website  — was assuredly worth the wait.

To burn off some of the excessive calories consumed in the previous 24 hours, a Sunday afternoon hike was in order. A quick, stunning drive east along the Columbia River transports you to series of waterfalls called Bridal Veil, Horsetail and Multnomah. Multnomah Falls is 600+ feet tall — no small trickle — and provides plenty to gawk at. Hiking trails take you throughout the area. Camera = must have. Although urban hikes are plentiful in Portland — according to our tour guide Sarah, Forest Park is the largest urban park in the world – it was nice to see some nature.

Our last dinner was at Ox Restaurant and it lived up to the hype. Because of the insane shunning of reservations, you have to go literally at 5 and hang out until 7 when you might actually be hungry; or stop by, slap your name on the list and come back; or, the old-fashioned way, know someone who works there. We had to go with option #1. Three delicious words: Bone Marrow Chowder. Who thinks of this sort of amazing concoction? Thankfully, the chef at Ox did, since it rocked my world. Again, worth the wait.

By Monday morning, it became clear that 72 hours wasn’t near enough time to explore Portland, but it definitely provided an appetizer for a future trip. There will be a next time for us since these are the things we didn’t do but wish we had the time: Multnomah Whiskey Library, Japanese Garden, the brewery scene, Hawthorne district and Powell’s City of Books. Yep, next time.