Weekend Guide to Portland

weekend guide portland


A Weekend Guide to Portland


Portland is undoubtedly one of the most unique cities in America and takes the utmost pride in that fact.  So much so, that the word “weird” is actually a term of endearment in Portland and a welcome descriptor for the culture that resides here.

The city boasts an abundance of quirky shops, a progressive culture, and one of the most vibrant music scenes in the US. The area’s abundant nature is also emulated within the best of Portland’s food, drinks, and attractions. If you’re looking for great coffee and locally sourced food, a bike ride, and a beer or a good reason to turn off your phone and smell the roses, a weekend in Portland has you covered.

Taking in the Scenery

Portland, abbreviated by locals as PDX, is the largest city in Oregon; a lush, artsy sprawl nestled between the Cascade Mountain Range and the Oregon Coast Range and along the Willamette River. Whether you’re taking in the city’s warm, dry summers or cool, wet winters, a trip to Portland is deeply connected to its beautiful surroundings.

With over 10,000 acres of parks, it’s difficult to miss the natural beauty in the city. Washington Park alone covers more than 400 acres with 15+ miles of trails linked to Pittock Mansion, the expansive neighboring Forest Park and more.

In Washington Park alone you can check out the wildlife at the Oregon Zoo, learn about the history of the Portland timber industry and national parks at the World Forestry Center Discovery Museum, take a romantic walk in the Hoyt Arboretum, get in touch with your inner child the Portland Children’s Museum, see and smell why Portland is known as the City of Roses at the International Rose Test Garden and get lost in the gorgeous scenery at the Portland Japanese Garden.

Once you’ve taken in Washington Park, head to Chinatown to visit the Lan Su Chinese Garden; a walled-in square city block of gorgeous trees, orchids, bamboos and other plants influenced by classical gardens in Portland’s sister city, Suzhou.

Bicycle-Friendly Downtown

Portland is frequently voted one of the most bicycle-friendly places in America, and many locals would contend that the best way to see the city is by bike. Embrace two-wheeled culture with a rental from Biketown, an affordable smart-bike service available at over 100 locations around the city.

While you’re at it, stop by Pioneer Courthouse Square, also known as Portland’s Living Room, then soak up the beautiful view from Tilikum Crossing, a cable-styled pedestrian bridge that crosses the Willamette River.

Did you know that Portland was almost named Boston? Learn how Portland’s name was decided by a coin toss at the Oregon Historical Museum and visit America’s largest independent used and new bookstore, Powell’s City of Books.

For a walk on the wilder side, there’s the one-of-a-kind experience of oddities and urban legends at The Freakybuttrue Peculiarium and Museum and the chance to get your haircut by a former professional basketball player at the Terrell Brandon Barber Shop.

Breakfast and Brunch Are A Must

You can’t have a serious conversation about Portland without coffee and doughnuts. Check out Coava and Stumptown Coffee Roasters for a great cup of joe, and find out why “the magic is in the hole” at the legendary Voodoo Doughnuts. Just don’t forget to try the Reggie, regarded by many as the best chicken biscuit on the west coast, at Pine State Biscuits.

Food Trucks, Fresh Seafood and More

Portland’s foodie cred goes far beyond breakfast and brunch with a deep farm-to-table culture and a wide variety of renowned chefs cooking up everything from Thai street food to southern comfort fare.

For starters tickle your taste buds at one of over 500 food trucks and carts spread across the city. Cartopia, one of the most popular food truck pods (a group of food carts) on Southeast Hawthorne Boulevard, includes a covered, heated seating area and late-night options like Potato Champion and Chicken and Guns.

For all things sandwich, stop by Bunk, a dive-y restaurant that also hosts live music in the evenings. Take in the local fare at the Portland Farmers Market or stroll down Southeast Division Street for a variety of dinner options. Woodsman Tavern offers a taste of the bountiful fresh seafood in Portland, and Toro Bravo cooks up delectable Spanish tapas. Ringside Steakhouse is one of the city’s oldest family-owned restaurants using locally-sourced meats, while Blossoming Lotus offers a vegan fusion menu so flavorful you’ll forget its good for you too.


With over 100 breweries in the metro area, Portland’s world-renowned beer scene and a homebrewing community that has something for everyone. IPA lovers rejoice as you soak up the harvest from the #2 Hop Growing state in the US.

Marry the city’s love of bikes and beer at Hopworks BikeBar or go down the rabbit hole of choices at the cozy Multnomah Whiskey Library. Sip local brews and get a taste of the local music scene with live performances every night at Laurelthirst, a lively neighborhood bar, or pair your pint with music at the Doug Fir Lounge, a fashionable lounge take on a log cabin.

Simply put, there are far too many amazing things in Portland to take it all in during a single weekend. Between the hip, artsy neighborhoods, amazing food and drinks and surrounding natural beauty, it’s easy to get lost in the appeal. Don’t be surprised if you might start cuffing your jeans and really appreciating the city as you plan for your early retirement in Portland.

Written by Julia Cohan for DreamStreet Team

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