Long Weekends: 3 Days in Portland, OR
The iconic White Stag sign in Old Town Portland
Portland, Oregon is not only a wonderful city to explore for a few days—it also happens to be where I live. With so many unique neighborhoods, parks, and attractions, moving here a few years ago was pretty much a no-brainer. While Portland has continued to grow in popularity, it still manages to fly under the radar with a lot of tourists. But I’m of the opinion that Portland, OR should be on your list of places to spend a long weekend. It can be hard to narrow down the perfect three-day itinerary, because Portland has a lot to offer—but I’m going for it anyway! Here are some of my suggestions that I hope will help you:
Day 1: Arrive as early as you can and start your morning in the Pearl District with a delicious breakfast at Screen Door for some comfort food to fuel your expedition. If you’re not in the mood for a big breakfast, head to Kinnamon’s for their insanely delicious takes on cinnamon rolls. From there, walk over to Powell's City of Books – the world's largest independent bookstore. Spend a few hours perusing the stacks and getting lost in the endless bookshelves. Besides being a treasure trove for stocking up your bookshelf, Powell’s is also a great spot to pick up your Portland souvenirs.
Powell’s City of Books
Afternoons in Portland are perfect for exploring some of its beautiful parks. Take a hike through Forest Park, the largest urban forest in the United States, or visit the Japanese Garden in Washington Park. You’ll be ready for a well-earned rest in your hotel room at The Nines Hotel. If you are looking for a drink at happy hour, all you’ll need to do is head up to the roof of your hotel to Departure for a cocktail paired with some stunning views.
For dinner, head over to the Alberta Arts District, which boasts restaurants that feature local, organic, and farm-to-table fare. Try the tapas at Urdaneta before heading to underground (literally!) wine bar Les Caves for some delicious Oregon wines.
Broder
Day 2: Brunch is serious business in Portland, so an early start is recommended. Start your day with breakfast on trendy and bustling Mississippi Avenue, where you can shop at boutiques and peruse local art galleries after your Scandanavian-inspired meal at Broder Nord.
View of the St. John’s Bridge from Cathedral Park
In the afternoon, head to the Cathedral Park for a spell to enjoy views of the iconic St. John’s bridge. While you’re up that way, grab a beer at Occidental Brewing Co. — because craft beer and Portland are pretty much synonymous.
Voodoo Doughnut
Day 3: Start your day early with some donuts. Portland’s most famous donuts can be found at Voodoo Doughnut, but locals will likely tell you that Blue Star Donuts are the better choice. Either way, you’ll have a tasty start to your day. From there, hop in the car and head to the Columbia River Gorge. You should, of course, try to stop at Multnomah Falls (if you’re visiting May through September, you’ll need to purchase a timed-entry permit…and parking will still be very limited, hence the early start).
The next stop is the small town of Hood River, where you can stroll the quaint streets and watch windsurfers carve up the Columbia River before stopping for a brewpub lunch. Full Sail Brewing, Double Mountain Brewery & pFriem are all good choices. Enjoy the beautiful views—and maybe do a little light hiking—before heading back to Portland.
Hood River, Oregon
Before you head to the airport to catch your flight home, grab your last meal in Portland at Birrieria La Plaza. Just trust me on this—a meal from this highly-rated food truck is NOT to be missed.
Birrieria La Plaza
Hopefully, these suggestions give you a great idea of how to spend three days in Portland, OR. If you’d like the additional perks of having a trusted travel advisor plan & manage all of the details for you like the VIP you are, click HERE!
