Portland in a Weekend

Despite Carrie and Fred’s entertaining depiction of Oregon’s famed eclectic city on Portlandia, this Pacific Northwest town isn’t just known for its eccentric locals and never-ending rainy season. It’s also packed with charming neighborhoods, delicious eats and an array of weekend-worthy activities.



Get the lay of the land by starting your trip on the Portland Aerial Tram, a four-minute trip that takes riders 500 feet above the ground for spectacular 360-degree views of the city. You’ll end at South Waterfront, where you can continue with a stroll across the region’s first cable stayed suspension bridge to eastern Portland. Tilikum Crossing, the $135 million “Bridge of the People” completed in 2015, offers incredible views of the Williamette River and its white triangular stays pay homage to the nearby Mt. Hood. It’s also the longest multi-modal, non-vehicle bridge in the country, meaning you can walk, bike, or ride the bus across it–but no cars.

Hop up to Northeastern Portland for Friday nightlife. Hip neighborhoods abound on this quiet, more residential side of the river. The Alberta Arts District is an eclectic, vibrant neighborhood that teems with local shops, restaurants and bars. Head to Bye & Bye for vegan eats and creative drinks served Southern-style in mason jars. Nearby at  the Radio Room, you can cozy up to a fire pit or enjoy a drink from the heated rooftop patio. End your night with some late-night bites at The Grilled Cheese Grill, a school-bus-converted eatery serving fresh takes on the cheesy classic.


Make your way into downtown for the Portland Saturday Market (located just south of the iconic Burnside Bridge), where you can shop handcrafted jewelry, farm-fresh products, an array of food vendors and plenty of kitschy souvenirs to take home. You’ll walk past the historic Skidmore Fountain as you make your way down SW Ankeny St. to Voodoo Doughnut (cash only!) for a sugary treat.

Wash it down with a frothy drink from Stumptown Coffee Roasters–but not before pausing for a picture in front of the Keep Portland Weird mural across the street.

Continue down W Burnside St. to the Pearl Districts’ Powell’s City of Books, which touts itself as the largest independent used and new bookstore in the world.

Bibliophiles will get lost wandering the Powell’s rooms filled with endless aisles of books (don’t worry, you can pick up a map at the entrance). Don’t forget to stop in the Rare Book Room, home to thousands of autographed first editions and antiquarian reads, including the store’s oldest book: De Bello Judaica with De Antiquitate Judaeorum Contra Apionem, printed in Verona in 1480.

Outside, you might find the Typewriter Troubadour, who, when handed a topic, crafts one-of-a-kind poetry on the spot for you to take home.

Pause for a midday break at Lan Su Chinese Garden, tucked neatly away in the middle of 2nd and 3rd avenues in Old Town Chinatown. The teahouse in the gardens serves as a nice respite from Portland’s unpredictable weather and a place to refuel before continuing on the day.

If it’s a nice day, grab an orange bike from one of Portland’s BikeTown city rental stations and pedal through the Pearl District to the Alphabet District and NW 23rd St. for some of the city’s best shopping.

At night, head downtown for drinks. Beer enthusiasts can stop into Deschutes Brewery  while whisky lovers can sample the selection at Multnomah Whiskey Library.


After a late night out, Off The Waffle will be the perfect way to wake up and fuel for another day of fun in Portland. For something savory, order a Deer in the Headlights. But Nutella and strawberry-lovers will melt for the Beloved Bully.

Over in Portland’s west hills, take a tour of the historic Pittock Mansion. This turn-of-the-century chateau with forty-six rooms was built in 1909 for tycoon and Oregonian publisher Henry Pittock and his family. By 1958, the mansion had fallen into disrepair. But a collective effort from the Portland community helped the city purchase the French-Renaissance style mansion, saving it from demolition, and it’s been open to the public since 1965 and offers some of the best views of the city from its hilltop perch.

From the mansion, head to the Japanese Gardens to visit the International Rose Test Garden. From April to October, visitors are treated to over 500 varieties of colorful roses spanning over 4.5 acres.

Got more time in the city? Rent a car and visit the iconic Multnomah Falls, a 30-minute drive from Portland.

What are your favorite Portland spots? Share in the comments below! 

-The Wandering Alligator

3 thoughts on “Portland in a Weekend

  1. Staci says:

    You sure fit a lot in just one weekend! I would love to go to the Chinese and Japanese gardens. The riverfront market is so fun! It’s where I had my very first falafel.

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