Posted Apr 6, 2015

7 Things to Do in Portland Oregon for Twenty Somethings

You’ve read about it in travel blogs, heard about it from friends and have probably caught an episode or two of “Portlandia” as well. All of the rumors you’ve been hearing are true: Portland is as cool as everyone says it is, especially if you’re in your 20s. 

7 Things to Do in Portland Oregon for Twenty-Somethings

Portland will always remain one of my favorite cities to visit, mostly because I got engaged there when I was heading toward my late 20s. Immediately following the proposal, my now-husband and I piled into a photo booth at the beautiful Ace Hotel in the Pearl District and snapped four photos of our reaction. The photos still hang on our fridge today, and every time I make my morning coffee, it’s hard not to smile and think about the amazing time I had there.

Portland packs a huge punch for being a smaller city, and it’s really easy to get around with its clean and efficient public transit system. There are some things you can’t miss when living here as a young wanderer. Here are a few of my recommendations for fun things to do in Portland Oregon:

1. Taste the Sweet Life at Voodoo Doughnuts

When it comes to offbeat attractions in Portland, this place has to be near the top of the list. Needless to say, this isn’t your run-of-the-mill doughnut shop.

7 Things to Do in Portland Oregon for Twenty Somethings - Taste the Sweet Life at Voodoo Doughnuts

Treats offered here include the Marshall Mathers (complete with mini M&Ms™!), a bacon maple doughnut and a yeast doughnut filled with raspberry jelly and chocolate frosting that looks like a Voodoo doll (there is a pretzel “stake” included). You can even buy a collection of Rogue beers here. Donuts and beer? What’s not to love about this place?

 2. Make Your Way Across Beervana

Besides the amazing lush scenery that engulfs Portland, perhaps the best thing that the Willamette Valley is known for is beermaking. Portlandians love beer, especially the craft kind, and there are a lot of tasty suds to choose from. In fact, a lot of people refer to Portland as Beervana, according to TravelPortland. 

7 Things to Do in Portland Oregon for Twenty Somethings - Make Your Way Across Beervana

In the Pearl District and NW Portland neighborhoods, don’t miss Bridgeport Brewing Co., the Rogue Distillery and Public House (where else are you going to try a Sriracha stout?), Fat Head’s Brewery and the Deschutes Brewery and Public House. Standouts in the Central Eastside neighborhood include Cascade Brewing Barrel House, Burnside Brewing and Hair of the Dog.

3. Take a Bike Tour

There’s no better way to get to know a new city than on the street level, and luckily, there are miles and miles of bike lanes and paths in the City of Roses.

7 Things to Do in Portland Oregon for Twenty Somethings - Take a Bike Tour

Not only is this an eco-friendly way to see the city, but Cycle Portland Bike Tours also offers beer- and food-based Portland tours.

4. Sip and Swirl

Guess what? The areas around Portland are also making a name for themselves in the viticultural world. The wine flows freely here, so enjoy it. Though heading out into the Willamette Valley to test out the area’s renowned pinot noir could be cool for day trip, there are several urban wineries located right in the city. 

7 Things to Do in Portland Oregon for Twenty Somethings - Sip and Swirl

Some great ones to enjoy? The Southeast Wine Collective houses nine wineries in one building, but there are also other independent favorites like the Division Winemaking Company and Seven Bridges Winery.

5. Take the Scenic Route

Portlandians love the great outdoors– and to be fair, they can’t help it because there are so many natural wonders to see here. You can drive to Mt. Hood National Forest, which features a powerful and majestic peak located just 20 miles east of the city.

7 Things to Do in Portland Oregon for Twenty Somethings - Take the Scenic Route

There is also Multnomah Falls, which is also right outside of Portland near the Oregon/Washington border. Here you can enjoy day hikes (the trails are pet-friendly so feel free to bring along your favorite furry friend, so long as he or she is on a leash) and of course, fantastic views of the falls. 

Trying to escape the urban atmosphere for the day? No problem. Check out the aptly named Forest Park, a sprawling green space located on the west side of the city– just 10 minutes by car from downtown. Here you can see beautiful sights like the Willamette River and go off the grid on 70 miles of walking and hiking trails. In fact, according to Time Magazine, this is the largest wooded urban park in the U.S. — so there are few places in the country this majestic if you happen to be a nature lover.

6. See America’s Fastest-Rising Sport in Action

After the 2014 World Cup, Americans caught soccer fever, especially in Portland. There are a handful of professional sports teams in the area, but few are loved more than the Portland Timbers. If you’ve never been to a Major League Soccer match, trust me, this is a great place to see the spectacle of soccer in all its glory. 

7 Things to Do in Portland Oregon for Twenty Somethings - See America's Fastest-Rising Sport in Action

As an historic tradition at Timbers matches, Timber Joey (the team’s mascot, which is a true-to-life lumberman) comes out to saw off a slab of a log after every Timbers goal. The slab is then presented to the player who scored the goal following the match. Where else are you going to see something like that in professional sports?

7. Channel Your Inner Bibliophile at Powell’s Books

Don’t miss this spot. This was easily one of my favorite places in the city. Even if you aren’t a big reader, there are a lot of reasons to spend an afternoon in Powell’s, especially if you catch yourself in the Pearl on a rainy day (which is very likely to happen in Portland).

7 Things to Do in Portland Oregon for Twenty Somethings - Channel Your Inner Bibliophile at Powell's Book

The sheer size of the used and new bookstore is almost overwhelming when you walk in (they call it “City of Books” for a reason), and there is bound to be a book with your name on it here.

There is, of course, plenty of fresh coffee to go around, too. Be sure to make time for the fascinating rare book room with works dating back to the 17th century and spanning from Africa to Europe. If you need to send some visitors home with a souvenir, this is the place.

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Photo Credit: Holly HayesNathalie ConeElly BlueJoe AbbruscatoDolan HalbrookRay TerrillSean Davis

Rachel LaCroix


Rachel LaCroix is from the Music City, but she now calls the Windy City home. In her spare time, Rachel enjoys writing, reading, seeing local bands, frequenting Chicago eateries, playing with her adorable schnauzer and, most of all, traveling. She's seen Costa Rica to Copenhagen and loves it all!

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