How to Plan the Perfect Weekend in Portland

February 20, 2018   No Comments »

How to Plan the Perfect Weekend in Portland

February 27, 2018 No Comments »

In an effort to bring you some new voices on Ottsworld, here is a guest post from a fellow blogger and Portland Oregon resident Susan Stephens. She had laid out a perfect weekend itinerary for her home town of Portland!  All opinions and experiences expressed here are hers. –Sherry

Portland, Oregon is a collection of diverse neighborhoods, each with their own ‘small town’ feel. These neighborhoods together weave a tapestry of everything that a big city offers. Portland has plenty of culture and entertainment, while also providing a sense of familiarity and friendliness found in smaller communities.

Most of us who live here are transplants. You have to look hard to find someone who was born and raised in Portland. We 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 subtle draw that makes you want to come back time and time again.

I often get asked for local Portland travel advice; if you had a ‘perfect weekend’ in your hometown, what would you do? Very often I find myself fantasizing about my ‘perfect weekend in Portland.’ If I had no obligations, nowhere to be and money was no object, what would that look like? Well, allow me to indulge…

How a Local Would Spend a Weekend in Portland Oregon

Saturday: My Favorite Day of the Week

I start my perfect weekend by going to school! Well, yes and no. The beautiful campus of Portland State University (my alma mater) hosts its popular farmers market every Saturday. Not only do they have dozens of vendors offering up fresh produce, locally made honey, breads, jams and flowers, but there are also several made-to-order food vendors. This is where Pine State Biscuits got their start (more on them later). As Portland’s year-round flagship market since 1992, during the spring and summer months they also have chef demonstrations and live music.

There’s a Rumbly in My Tumbly

Time for breakfast! I 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? I usually opt for my favorite, 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 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. I rarely walk out of there empty handed. As you walk along the boulevard there are lots of shops and restaurants to explore.

Further down the street is McMenamins Bagdad theatre. It’s in a historic, Mediterranean-styled building reminiscent of Hollywood’s golden age. I’ll usually catch a show in the afternoon if I’m in the area, 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! The park’s rise in elevation gives you a killer view of downtown Portland to the west.

A Foodie Destination

So now that I’ve had my exercise, it’s time for more food! Hey, this is supposed to be my ‘perfect weekend’ so I’m indulging! After all, Portland is a foodie destination. Tapalaya is one of my favorite restaurants serving a fusion of Creole/Cajun and Vietnamese-inspired tapas (small plates). Chef Anh Luu grew up in New Orleans, so she knows her stuff. She’s even been on the TV show, Chopped! She didn’t win the competition, but she should of; her talent shines through in every single bite of her creations.

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. The pool is where I’m headed. 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 I’m off to 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), I’ll 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 I’m not feeling a stunning riverwalk along the Portland city skyline, I’ll 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, I like to drag my coffee-craving, brunch-loving, hipster-embracing self to a nearby coffee shop. I frequent Grendel’s or Coava Coffee Roasters. Portlanders are as serious about their coffee as wine connoisseurs are about their wine. There’s so many great coffee houses to choose from all over town.

Shopping, Street Art and BBQ, Oh My!

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. 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 corn bread drizzled with honey. YUM.

Now for Desert

I’m rounding out my perfect Portland weekend with ice cream! For this I go back to Mississippi Avenue, to Ruby Jewel Scoops. They offer a rotating array of unique flavors, along with the usual suspects. It was hard to choose between the Honey Lavender and the Creme de la Earl Grey + Chocolate. Mississippi Ave has a plethora of unique, locally owned shops, restaurants and bars.

How to Visit Some of the Places Mentioned

PSU Farmers Market
A Map of Portland’s Food Carts
Hawthorne Neighborhood
Portland Street Art App
Mississippi Avenue
Forest Park

If you find yourself looking for things to do for a weekend in Portland, 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. I’ve been here 20 years and I still haven’t seen it all! Like the finest treasure, Portland is equal parts magnificent and melancholy, wild and tame, uncomfortable and cozy. Bottom line is, Portland is everything. At least to me! I hope you’ll come visit and see for yourself all that Portland, Oregon has to offer.

Meet the Author

Susan Stephens is a scientist-turned-travel-writer and a transplant from the Midwest. She has lived in Portland, Oregon for over twenty years. Her travel blog is dedicated to helping people discover the beauty of the Pacific Northwest. Please visit her website – Explorer Sue – to start planning your next Pacific Northwest adventure!

You can follow her on:  Instagram @pdxtravelgal  |  Facebook ExplorerSue  |  Twitter @PDXTravelGal  |  Pinterest ExplorerSue

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