Blogging over 5 years ago by Liz Adams

Weekend Guide to Portland, Oregon

Weekend Guide to Portland, Oregon

Happy Saturday! Carolyn here. As some of you may know, Chicago is my current base, but I’ve spent the summer in and around my hometown of Portland, Oregon. I haven’t had this much time at home in a loooong time, so it’s been pretty wonderful to soak up lots of nature, watch Saturday night movies with my parents just like the old days (very exciting, I know) and hit up the ever-incredible Portland food scene with my high school friends. Many of my peers in the Midwest have never been to Portland, so I thought I would put together a mini weekend guide for you! Here are a few of my favorites things to do, eat and see if—and when—you visit. 

Where to Stay:
I always stay at my parents’ house when I come to Portland, of course, but I’ve heard/seen amazing things about the Airbnb options in Portland. Generally, I would recommend staying in the Pearl District or around NW 23rd Avenue (the Alphabet District). The area around my high school is actually super hip now, too—check out NE 28th Avenue or Alberta Street. In terms of hotels, I would recommend the following: 
The ACE Hotel 
The Kimpton 
The Nines 
The Heathman 

Things to do in the city:
– Head up to Washington Park and take a stroll through the International Rose Garden. Even if you aren’t into plants, it’s pretty spectacular, and there are great views of Mt. Hood on a sunny day. I would also suggest buying tickets to the Japanese Garden, which is a little bit newer and so beautiful and calming. 
– Visit Forest Park, a 5100-acre old-growth forest with running and hiking trails right in the middle of the city (my favorite trail is Wildwood, which you can pick up at Lower McLeay and take all the way up to Pittock Mansion). Needless to say, make sure to wear shoes you don’t mind walking around in while in Portland. Nikes are more than welcome, and you can wear the most casual clothes to even the nicest restaurants in Portland. 
– Check out Powell’s Books, the largest bookstore in the world. It’s super quirky and overwhelming, but classic Portland. There are a few fun stores in this area of the city, including a really nice REI and a two-story Anthropologie. No sales tax in Oregon, wink wink. 
– Stroll up and down NW 23rd Avenue—lots of cute boutiques and some stellar dessert options if you have a sweet tooth. There’s Salt & Straw ice cream, of course, but my favorite restaurant EVER since I was little is Papa Haydn. Order the Boccone Dolce, you won’t regret it. 

Things to do Outside the City: 
Several amazing day trips are just a short drive away from downtown. My top three recommendations would be the Oregon Coast, the Columbia River Gorge, and wine country. They’re all in slightly different directions, so you may not have time for two trips in one day, but each is worth a day on its own. 
The Oregon Coast: drive to Cannon Beach, grab a coffee at Sleepy Monk and walk along the beach to Haystack Rock (pictured above). I like to drive a bit further down towards Cape Lookout State Park—we saw two grey whales right off shore while hiking here in June! We also discovered a hike called “Short Sand Beach” in Oswald State Park on that trip—it’s a bit trickier to find (you basically just pull into a parking lot off the highway), but it ends in a magical, sparkling beach full of tidepools. I’d never seen anything like it before! 
The Columbia River Gorge: Jaw-dropping, gorgeous views, and endless waterfalls. See Multnomah Falls and then hike Angel’s RestWahclella Falls (a quintessential Columbia River Gorge hike) or Dog Mountain if you’re looking for a workout. 
– Willamette Wine Country: pick up picnic supplies at Whole Foods or New Seasons and then drive to the Willamette Valley for a classy day of wine-tasting. You really can’t go wrong here, but I’ve been to + loved Domaine Serene, Sokol Blosser and Domaine Drouhin

What to eat/drink: 
Oh man, this list was a hard one to narrow down. I can’t claim to be the most up-to-date on the ever-changing Portland food scene (I’m simply not home enough) but my best friend from high school keeps a very in-depth Google doc, complete with very in-depth reviews and ratings. A few of our personal recommendations for a classic Portland dining experience: 

Ken’s Artisan Pizza 
Henry’s Tavern 
Pok Pok 
Boxer Ramen 
Kenny & Zuke’s 
Por Que No? 

 Laurelhurst Market 
Toro Bravo 
Le Pigeon 

Brunch + Breakfast: 
Proud Mary (my favorite) 
Grand Central Bakery 
Tin Shed 
Lovejoy Bakery 

Cafe Umbria 
Sisters Coffee House 

Salt & Straw 
Ruby Jewel 
Woodblock Chocolate 
Papa Haydn 
Bluestar Donuts 
Pip’s Donuts 

Bars + Breweries: 
10 Barrel 
Deschutes Brewery 
– Stammtisch
– Hopworks Urban Brewery
Revolution Hall 

Have any of you been to Portland, Oregon? I’d love to hear about your favorite things to do in the Rose City! 


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  1. We went for the first time this Memorial Day and loved it! Cascade and Modern Times breweries were our fav! We stayed in Pearl District and walked everywhere! Besaws in Slabtpwn is adorable and delicious!!

  2. Thank you so much for your city guides! My husband and I traveled to Chicago in June and followed your recommendations… every one of them exceeded our expectations. I went to nursing school on NW 23rd and have spent a lot of time in Portland. I might add for a quick grab and go or stay and eat lunch to check out Elephants Delicatessen… I also love Mother’s Bistro for breakfast/brunch. If you plan to go wine tasting, stay a night in McMinnville! They have the 3rd street flats that you can rent that are fabulous. Drive out to Amity for wine tasting at Brooks winery and pick apples afterwards at the orchard below the property… so much to do, thank you for these great recs. I will have to try a few next time I’m in Portland!

  3. Curious what months (weather wise) you would recommend visiting? I’d love to not go during top tourist season, but also want to enjoy the cool PNW climate (especially as a Floridian). Looking to plan a trip for 2019!

    1. I would visit in September—the BEST month in Portland, by far! October is pretty nice, too, and you may get some of that cooler weather you are looking for!