Portland, Oregon is a collection of over 100 diverse neighborhoods, each with their own small-town feel. Together they weave a tapestry of everything that a big city has to offer. Portland has culture and entertainment galore, while also providing a sense of familiarity and friendliness found in smaller communities.
Most people are transplants. You have to look hard to find someone who was born and raised in Portland. They come from all over the globe. In this way, Portland is teeming with diversity; so many ideas and creativity in one place give the Rose City it’s life-force, it’s a subtle draw that makes you want to come back time and time again. Portland is a 60’s throwback or a hipsters paradise depending on your age and outlook. We going to start with the funky side of Portland and end with the tourist stuff.
I’ve been asked for Portland travel advice; if you had a weekend in Portland, what would you do? So, a ‘perfect weekend in Portland; If I had no obligations, nowhere to be and money was no object, what would that look like? My take..
Friday, My Favorite Day of the Week
I start the weekend by going to school! The beautiful campus of Portland State University hosts its iconic farmers market every Saturday. With dozens of vendors offering up fresh produce, locally made honey, bread, jams, and flowers, there are also several made-to-order food vendors. This is where Pine State Biscuits got their start more on that in a bit. As Portland’s year-round flagship market since 1992, during the spring and summer months they also have chef demonstrations and live music. An eclectic gathering to say the least.
Time for breakfast! I would head on over to the Hawthorne neighborhood, to the Fried Egg I’m in Love food cart. You can’t miss it – it’s bright yellow, I guess to represent an egg yolk? One of my favorites, the Yolko Ono breakfast sandwich. A fried egg, homemade pesto, and a hand-pressed sausage patty inside perfectly-grilled sourdough bread. The result? Breakfast heaven. Other notable favorites on the menu are the ‘Rito Suave burrito and Smells Like Protein Spirit sandwich. See a music theme going on here?
Across the street on Hawthorne Boulevard is the Red Light Clothing Exchange. This funky space is a second-hand clothing mecca, with a huge variety of men’s and women’s duds in all sizes. Not my style clothing but a cool place to explore. As you walk along the boulevard there are lots of shops and restaurants to explore.
Further down the street is McMenamins Bagdad Theatre and Pub. It’s in a historic, Mediterranean-styled building reminiscent of Hollywood’s golden age. It’s a great place to catch a show, because why? You can order a slice of pizza and a beer to enjoy during the movie!
Just down the road from Hawthorne is Mt. Tabor Park. Set on a dormant volcano, it’s a great place to walk off that pizza and beer, and a great place to walk your dog if you brought one! If not, borrow one because everyone has a dog in Portland. The park’s rise in elevation gives you a killer view of downtown Portland to the west.
A Foodie Destination
Now that you’ve exercised, it’s time for more food! Hey, this is supposed to be a ‘perfect weekend’ so you can indulge! After all, Portland is a foodie destination. Maurice luncheonette is one of my favorites. In a bright, beautifully appointed hole-in-the-wall venue near Powell's Books, Kristen D. Murray delivers exactly what Portland didn't know it needed: an incredibly charming "pastry luncheonette" that focuses equal attention on sweets and savory fare. The result is one of the city's top leisurely lunch and dessert experiences. A great laid back place to rest your puppies for lunch.
Next stop is the Kennedy School Hotel. This is a (yep, you guessed it) historic converted schoolhouse that is a destination unto itself. They have several restaurants and pubs, a movie theatre, and a soaking pool on site. If you are not a guest of the hotel, for a mere five bucks you can have a relaxing hot soak in their private outdoor courtyard.
It’s Saturday night, so catch a show at Mississippi Studios, a music venue hosting both local and international acts on any given night. Located on Mississippi Ave, it’s an intimate space with a full bar serving burgers and sandwiches right next door. Portland has an abundance of home-grown musical talent, and this is a popular venue for artists to hone their chops.
Sunday: The Adventure Continues
Earlier I mentioned Pine State Biscuits. These guys quickly graduated from a food cart to a brick-and-mortar with four locations! Their signature item, the Reggie Deluxe, is a flaky homemade biscuit holding a perfectly-cooked fried chicken breast underneath bacon, cheese, and a fried egg. Get there early or suffer the line!
If it’s a nice day (i.e. not raining), head downtown and take a walk or bike ride on the East side esplanade along the majestic Willamette River. A three-mile loop will take you across two of Portland’s many bridges to the picturesque Tom McCall Waterfront Park and back. If you’re not feeling a stunning riverwalk along the Portland city skyline, go to Forest Park (one of the largest urban parks in the U.S.) and hike up to the Witches Castle. It’s presumably haunted!
What’s a weekend in Portland without coffee? After a scenic workout, drag your coffee-craving, brunch-loving, hipster-embracing self to a nearby coffee shop. Try out Grendel’s Coffee or Coava Coffee Roasters. Portlanders are as serious about their coffee as wine connoisseurs are about their wine. There are so many great coffee houses to choose from all over town.
Shopping, Street Art, and BBQ!
I’m not much of a shopper, but I do love to browse unusual stores, and Cargo fits the bill. They directly import their goods from around the world, including gifts, home decor, furniture, and textiles. The perfect place to shop for that hard-to-shop-for person.
One of the great things about Portland is the street art! As you meander around town, you cannot help but run into several fantastic murals and sculptures. There are hundreds all over town. There is even an app you can download that will show you a map of all of the current street art, much of which is commissioned by the city.
Another food cart-turned-restaurant is People’s Pig Restaurant. The BEST BBQ in all of Portland. Vegetarians beware! Order your pig tucked in a sandwich or by itself, with a side of collard greens and house-made macaroni salad. And don’t forget the side of cornbread drizzled with honey. YUM.
I hope you’ll go local and try out some of the shopping, food, outdoor space, and art. The places I’ve mentioned are just the highlights. Like the finest treasure, Portland is equal parts wild and tame, magnificent and melancholy, uncomfortable, and cozy. That’s to say, Portland has a little bit of everything.
Now to the top tourist things you don't want to miss:
- Portland Saturday Market
- Lan Su Chinese Garden
- Portland Art Museum
- Oregon Museum of Science and Industry
- Forest Park
- Multnomah Falls
- Mount Hood
- Oregon Zoo
Two great hotels and a Bed and Breakfast:
- The Woodlark Hotel Great hotel in a great location.
- The Press Hotel I'm biased to Marriott hotels having spent over 3 years of my life sleeping in their rooms all around the world and this is one of their top-notch Autograph Collection hotels
- The Chadwick Bed and Breakfast