Portland is a big city with a small town feel and a great deal of pride for being home of the weird. Spend a long weekend exploring the funky neighborhoods and enjoying the laidback atmosphere. Go if you love beer, go if you love rain, or go just for fun and you’ll find yourself falling in love with this quirky place.
See and Do
Powell’s City of Books
Get lost in this behemoth of a book store where the aisles of books seem to go on forever and ever. I, of course, suggest checking out the food and wine aisle where you can see new releases cozily tucked up against old favorites. Book lovers should plan for at least an hour of browsing but you may get lost for longer.
St. Johns Bridge
It’s worth the jaunt out of the city to check out this steel suspension bridge from nearby Cathedral Park. The delicate Gothic details of the bridge against a background of greenery and the river below make for a peaceful, reflective moment. Once you’re done checking it out, head up the hill to the Occidental Brewing Company for a beer and a pretzel or sausage plate if you’re hungry.
Portland Art Museum
Located at the southwest end of Downtown, a visit to this mid-sized museum is a must. You can easily spend a few hours exploring the modern exhibits temporarily on view and permanent collection of Native American art and European classics. Be sure to check out some of the activities for kids and adults that are offered throughout the museum.
Southeast Division Street
Spend an afternoon strolling down this hip street. Browse chic women’s clothing at Adorn, curated accessories and home goods at Field Trip, or the cutest eco-friendly paper goods from Little Otsu. If you can stomach the line, wait for Chef Andy Richter’s famous Thai chicken wings at Pok Pok. It’s also worth checking out Salt and Straw for an ice cream or getting a drink from the Whiskey Soda Lounge, Imperial Tap Room, or Division Wines.
Zero Waste Experience
Portland is one of the most environmentally conscious cities in the world with it’s abundance of farmer’s markets, food coops, secondhand stores, and sustainable businesses. My friend Chloe has created the Ultimate Zero Waste Guide for Portland complete with a detailed Google Map and option to book a tour of her home so you can learn how to live a life geared towards less waste.
Eat and Drink
Olympia Provisions Southeast
Some of the best food in Portland lies amid a bunch of industrial buildings. The menu is a nod to European comfort food, which is reflected in the sleek yet cozy cafe vibe. Start with a charcuterie board and then go for a hearty main dish paired with a wine from the Old World.
Tucked away on the northeastern side of Portland, this place is redefining the term “neighborhood joint.” The statement wallpaper is perfectly paired with the modern bistro-style decor just like the natural wines are perfectly paired with the seasonal and sustainable veggie-centric dishes. Go for an appetizer of fried anchovies with a glass of wine or make reservations for an intimate dinner for two.
Microbreweries abound in Portlandia with one on practically every corner. Not to mention, most of the local watering holes serve up high-quality IPAs, sours, and ales. We enjoyed a sampler and the laidback atmosphere at Deschutes Brewery. You also can’t go wrong at Belmont Station, Saraveza, Culmination and Ex Novo.
Anyone in need of high-quality coffee should seek out one of Stumptown’s five locations in Portland. We enjoyed getting our morning cup at the downtown location with it’s brick walls, modern design, and people-watching (weird is so wonderful, no?).
No trip to Portland is complete without a stop at the place that launched a nation-wide obsession with bacon maple bars and unconventional fried donuts. There’s usually a line (rain or shine) but that’s part of the experience. While there, you might as well get your pic taken in front of the Keep Portland Weird mural across the street.
Previously a boarding house for sailors, the Society Hotel in Downtown Portland has been transformed into a boutique hotel where you can rent a private room or stay in one of the shared hostel-style rooms.
Rooms are minimally designed (in a good way) and crisp sheets make for a comfy bed. Just don’t forget to pop in the provided ear plugs, those old walls are super thin! Get a cup of joe from the coffee bar in their lounge and, once the clouds clear, grab a beer and go upstairs to enjoy the view from the roof-top terrace.
If you’re ready to splurge, head on over to the Ace Hotel and enjoy all the hip luxury they have to offer there.
Tips and Tricks
It’s fairly easy to get around in Portland. We loved staying in the Downtown historic area where everything is within walking distance. Get a Lyft or Uber if and when you want to go on an adventure.
Rain is part of the weather report most days in Portland. It’s a fairly casual town where outdoor gear is totally acceptable as everyday wear. Layers are also a good idea as the temp can sometimes change quickly.