How to Plan the Perfect Weekend in Portland

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 hometown of Portland!  All opinions and experiences expressed here are hers. –Sherry

Portland, Oregon is a collection of diverse neighborhoods, each with its 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 its life force, its subtle draw that makes you want to come back time and time again.

How a Local Would Spend a Weekend in Portland Oregon

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…

Weekend in Portland Map

Here’s a custom map I made to make it easier for you to locate some of these special places for your weekend in Portland.

Perfect Weekend in Portland – Saturday

I start my perfect Portland 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, bread, 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.

Start in the Hawthorne Neighborhood

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? See Other Portland Food Cart options 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.

Plan 2 days in Portland, Oregon – spend a weekend eating donuts and working them off!

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.

Take a Dip at Kennedy School Hotel

The 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.

Catch Some Live Music

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.

Read reviews for Portland hotels on Trip Advisor | Search and book a hotel in Portland

The Perfect Weekend in Portland – Sunday

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!

Take an Urban Hike

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!

For more ideas on things to do in Portland, check out these Get Your Guide popular Portland tours:

Get Serious About Your Portland Coffee

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 are so many great coffee houses to choose from all over town.

Shopping and Portland’s Street Art Scene

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 a map you can download that will show you a map of all of the current street art, much of which is commissioned by the city.

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Try the Best BBQ in Portland

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 cornbread drizzled with honey. YUM.

We All Scream for Portland Ice Cream

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.

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 to visit and see for yourself all that Portland, Oregon has to offer.

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