"Portland Is Where Young People Go to Retire," and 21 More Reasons to Go

Alivia Latimer for MyDomaine

Fred Armisen and Carrie Brownstein said it best: "Portland is where young people" (and foodies) "go to retire." Cheeky, yes, but also incredibly poignant. And we can see why so many people are flocking to this small, idyllic city in the Pacific Northwest, both for the long haul and for a stateside vacation. Since there are a plethora of destinations to choose from and time off is precious, we thought we'd help out by providing local tips to make sure you get the most out of it.

We teamed up with Tonya Smith, the stylish Portland-based influencer behind The Moptop, to compile an insider-curated city guide. Aside from telling us about all her favorite spots, Smith also shares some of her street style moments, so you can get inspired while you pack. Read on to find out all the best things to do in Portland, including where to stay, shop, dine, and explore.

Alivia Latimer for MyDomaine

Where to Eat

Alivia Latimer for MyDomaine

Clyde Common: With dessert items like a plum vanilla float on the menu, it's safe to say that this place is a foodie heaven. "I love the atmosphere of Clyde Common. The open interior just feels so welcoming, and it has quite a good happy hour," says Smith. So come for drinks, and stay for dinner and dessert.

Maurice: With a menu that changes seasonally to ensure that patrons only enjoy the freshest ingredients and flavors, you can always expect something interesting, delicious, and locally sourced from this little French-inspired bistro. This self-proclaimed modern pastry luncheonette also presents everything beautifully, so your Instagram feed will thank us.

Alivia Latimer for MyDomaine

Castagna: Come here for the fine dining experience of a lifetime (or go to its café for something a bit more casual). It's a Portland classic that you shouldn't miss if you're in the culinary scene.

Ava Gene's: This restaurant serves up the best homemade pasta in the area. Enjoyed family-style, this is a great place to come for comfort food with loved ones. The spot also has a great carousel of highlighted pasta dishes each day of the week.

Vivienne Kitchen & Pantry: Smith makes a good point when she asks, "what's not to love about this place?" Vivienne is a charming gem in the Hollywood District, and it's perfect for coffee dates, a casual lunch, or happy hour drinks. "I love the interior design and the plants that line the place. It's exactly how a restaurant should be and make you feel," Smith says.

Where to Drink

Alivia Latimer for MyDomaine

Prince Coffee: This is the perfect spot to enjoy your morning cup. Smith tells us that "this little coffee shop is located in the Kenton neighborhood in Portland, [and] even though it's a little bit of a drive from my house, it's worth it. I love the stroopwafels and the beautiful décor."

Multnomah Whiskey Room: The most popular watering holes in Portland tend to be breweries, but there are plenty of options for those of you who want something more formal. Multnomah Whiskey Room features brooding retro interiors, so it's a unique way to experience the city's nightlife while sipping on high-quality spirits.

The Boiler Room: This dive bar is super fun for a girls' night out. You can drink, dance, and dine here, but our favorite part is the karaoke.

Where to Shop

Alivia Latimer for MyDomaine

Solabee: "This is one of my all-time favorite shops in Portland. I love picking up some new plants for my apartment here or to just soak up as much inspiration as I can. This place is a local gem," Smith shares with us.

Frances May: If you love following fashion trends and plan to shop while you're in the Portland area, you can't miss this chic multi-brand boutique for men and women. It carries its own brand of reclaimed vintage pieces, as well as lines like Rachel Comey, Common Projects, Grlfrnd denim, and more.

Alivia Latimer for MyDomaine

Association: If you love the laid-back yet cosmopolitan look of Southern California style, check out Association. "This shop reminds me so much of Los Angeles. Its pieces are displayed so beautifully that it almost feels like you're in a museum," Smith says.

Canoe: For artfully designed home goods, Canoe is the place to go in Portland. While we particularly love its décor items, furniture, and kitchen accessories, the shop also has cute knickknacks that make great gifts, plus some elevated baby and pet supplies.

Alivia Latimer for MyDomaine

Woonwinkel: "This quirky little shop is a fun place to stop by" for everything from jewelry to tapestries and textiles. "You never know what you might find there, but you're sure to get inspired just by going in," Smith assures us.

Little Axe Records: Music junkies shouldn't miss this record shop while they're in Portland. "There are so many great record shops in town, but I love this one especially because of how intimate it is," Smith explains. "Not to mention the amazing vinyl" that you can only find here.

Stand Up Comedy: This is your one-stop shop for beautiful, one-of-a-kind clothing, accessories, home goods, and books. With thoughtfully creative labels like Issey Miyake, Eckhaus Latta, Maryam Nassir Zadeh, Maison Margiela, Alexa Stark, Lauren Manoogian, Baserange, Martiniano, and Mari Giudicelli, the only problem is not wanting to take the whole store with you on your way out.

Where to Stay

Alivia Latimer for MyDomaine

Ace Hotel: This hip spot is located in what used to be the historic Clyde Hotel building in the middle of downtown Portland. And while we recommend exploring the many coffeehouses, restaurants, and shops throughout the city, you technically wouldn't have to leave the lobby to get your fair share of gourmet eating and stylish shopping. It's also pet-friendly if you want to bring yours on vacation with you.

The Nines Hotel: For something a bit more grown-up, consider staying at The Nine Hotel. With panoramic rooftop views, museum-worthy artwork, and a vibrant lobby, it's the perfect place to unwind after spending the day exploring the city.

What to Do

The 4T Trail: Hiking the 4T trail is a great way to enjoy the natural beauty in the surrounding Portland area. You'll get to take a trolley, a tram, and a train in one day as you make your way to the trail. It's also the perfect way to experience the many different parts of Portland if you aren't visiting for long. Here's how it works: First, you "hike uphill among the trees from the Oregon Zoo to Council Crest Park—at 1073 feet, it's the highest point in the city—and then you enjoy an easy stroll down to Oregon Health and Science University, where you will board the Portland Aerial Tram and glide 3300 linear feet downhill to the riverfront. From there, board the trolley (aka the Portland Streetcar), and ride to the heart of downtown Portland."

Food Carts: If the stellar lineup of restaurants didn't already give it away, Portland is a foodie mecca. So if you still have room for more (and even if you don't), you should definitely spend an afternoon or evening trying something from each of the famous food carts.

John Day Fossil Beds National Monument: For another breathtaking spot to soak in Portland's natural beauty, visit the Painted Hills. It's also super close to the airport, so even if you can only stop by on your way in or out, the rainbow of rolling hills is worth seeing.

Nationale: As a hub for creatives, it's no surprise that Portland has some of the best galleries with work by both notable and emerging artists around. If you like checking out new art but prefer the intimate space of a gallery over larger museums, we suggest going to Nationale.

Shapes Rug 4x6
Hawkins New York Shapes Rug 4x6 $300
Lucy Michel Loop Vase $145
Michael Wall Pink Natural Painting $495
Cat eye sunglasses
Gucci Cat Eye Sunglasses $415
Mari Giudicelli Leblon Mule $514
Petite Alice Maison in Cream Woven
Clare V. Petite Alice Maison in Cream Woven $175

Related Stories