24 Hours in… Portland

Explore the weird and the wonderful.

Portland is famous for being wonderfully weirdly. From donut shops where you can say “I do” to vegan salons and hotels that lend you goldfish when you’re lonely, take a tour of the brilliant and bizarre with our one-of-a-kind city guide for 24 hours in the Portland.

Keep in mind that Portland essentials include a lightweight rain jacket, like our Mt. Crescent Waterproof Jacket for men and Rosebrook Waterproof Trench Coat for women, which is stylish, waterproof and light. Also, Portland is a great walking city, so a waterproof boot like our Chestnut Ridge Waterproof Chelsea Boots (in a variety of styles and colors) for men and our Stoddard Waterproof Biker Boots for women will keep you dry and comfortable during your Portland exploration.

Wake up at Hotel Monaco

This centrally located chic boutique hotel has eclectic touches, like the resident hotel lobby dog. You can borrow brushes, paints and easel to invoke your artistic side, or, if you get lonely, the hotel will even lend you a goldfish to keep you company - on the house, of course.

Have a coffee at Stumptown Coffee Roasters 

If you’re serious about coffee, Stumptown is a must. Considered one of the best roasters in the world, Portland is where the dynasty began. These guys take their morning cup of joe very seriously, traveling to all four corners of the earth to source the best coffee beans, so you don’t have to. Thanks, guys.

Grab a donut at Voodoo Donut

This iconic donut shop is a cult favorite. Their signature treat is a chocolate-frosted man filled with raspberry jelly to resemble a voodoo doll. You’ll find 50-plus flavors including the bacon maple bar donut and the Portland Cream (filled with Bavarian cream and complete with two “eyes” to represent the vision of the city). True donut-lovers can even get married here. I do!

Peruse records at Tenderloving Empire

Much more than just an awesome record shop, Tenderloving is a marketplace for handmade goods. From T-Shirts and dish towels to one-of-a-kind prints from local independent artists, the store is a microcosm of Portland’s creative scene.

Browse books at Powell’s City of Books

Covering an entire block, Powell’s City of Books is a literary lover's dream. Selling a combination of new and used books, Powell is a one stop shop whether you’re looking for a well-thumbed classic or a shiny new hardback to give as a gift. Of course, it has it’s own coffee shop, so grab a brew and get lost in their selection. 

Grab a second coffee at Coava

Why not? You’re in Portland, the best city in the world for coffee. Named as one of the 12 best coffee shops in the US, Coava combines great tasting coffee with cool design in their retail space. Airy, well-lit with smooth bamboo fixtures, Coava reflects Portland’s unique vibe. Their cold brew coffee is the best in the city.

Pick up some vegan clothing at Herbivore Clothing 

Selling a wide range of vegan-friendly clothing, including a line of vegan belts and wallets, Herbivore offers a spot of retail therapy for vegans and non vegans alike. Ready to refresh your wardrobe in an environmentally-friendly fashion? It’s the Portland thing to do. 

Grab dinner at Le Bistro Montage Cajun 

Aside from their incredible Southern food (including an impressive selection of mac n’ cheese) Montage Cajun is legendary for transforming your leftovers into a foil work of art. Over-ordering never felt so good.

See a movie at McMenamins Mission Theatre

Order drinks and watch a movie in this historic converted church. Located in Northwest Portland, McMenamins Mission Theatre boasts special movie screenings, live music, and engaging talks all washed down with Ruby Ale and Red Vines, or (seasonal) Cherry Cider. Enjoy!

Catch live music at Mississippi Studios 

Located in the historic Mississippi district, this renovated church has been turned into an intimate live music venue that serves some of the best burgers in town. Built, owned and run by and for musicians, this small venue regularly sees some big names playing on it’s stage, but also features up-and-coming talent. End the day by supporting Portland’s local music scene. 

Want to know more about the city? Portland is known for attracting and nurturing creatives, like our MarkMaker Benjamin Holtrop, a photographer in the city. He shares his photography tips, what inspires him and why he loves his hometown. Read our interview with him here (and see him model our Moto Collection).