Check out my article here on bay area.com too:
Weird? Some may think so, but Portland, Oregon is a city of many names and faces. It’s a food town and brew town which goes by the name of Stumptown, Rose City, Rip City, and more. You can get your fill of urban life here while also appreciating the beauty of nature with its breathtaking views of Mt. Hood and nearby waterfalls. Portlandians are a creative and eclectic bunch and their city is a reflection of that. So when visiting, be sure to take in all of the “weirdness” that is Portland on your 48-hour trip to this amazing city.
6:00 P.M. – PDX CARPET SIGHTING
Start your weekend adventure by taking a quick 90-minute flight up to Portland. As soon as you get off the plane, the infamous PDX carpet will be awaiting you and your camera, so be sure to snap a quick photo to mark the beginning of your mini vacation.
Pro tip: If you need a rental car for the weekend, there’s plenty available right across the street in the airport parking garage.
7:30 P.M. – DINNER ROULETTE
Head downtown to check into your hotel. I’d recommend staying at Hotel Eastlund, a boutique hotel with an ideal location. After you’ve unloaded your luggage, make dinner plans and get ready for your first night out on the town.
Portland is well known for its fresh, farm-to-table cuisine, so you’ll have plenty dining options to choose from.
I suggest heading to the Alberta Arts District to play some dinner roulette. On one corner, you’ll find Bollywood Theater which serves up fast Indian street food in a well-lit and beautifully decorated restaurant. Then, there’s Little Big Burger which locals say is even better than California’s own In-n-Out. I beg to differ, but their truffle fries are amazing and they have beer. You can also try have dinner next door at the Boxer Ramen which serves delicious bowls of thin noodle ramen.
Don’t forget to save room for dessert! The ever-so-popular Salt & Straw (coming soon to SF) ice cream shoppe is just a few doors down. Try their unique seasonal flavors or another interesting combo to satisfy your sweet tooth.
End your first day in Portland with a scoop of Salt & Straw ice cream
9:00 P.M. – TIME FOR A DRINK
After dinner, it’s time for a drink or two. Portland is filled with local breweries, cideries, and bars, such as Deschutes Brewery and Spirit of 77. Grab a pint of a locally brewed beer and relax before turning in for the night.
8:00 A.M. – BREAKFAST ON THE GO
Rise and shine! It’s time to head out the door and pick up a quick bite for breakfast. Portland is famous for its unique and gourmet donuts, giving you the perfect excuse to start off your day with a delicious treat. At Blue Star, you’ll find donuts with flavors like smoked grapefruit and passion fruit with cocoa nibs. Or if you’re looking for more familiar flavors with a Portland flair, head to the iconic VooDoo Doughnut and order a donut shaped like a VooDoo doll.
9:00 A.M. – FALL FOR THE FALLS
Once you’ve eaten, head 20 miles out of town to see some gorgeous waterfalls and views. First, drive out to the Vista House for views of the Columbia River Gorge, then go down to the iconic Multnomah Falls. Explore the wilds of Oregon and soak up some nature on a scenic hike.
1:30 P.M. – LUNCH N’ BOOKS
After being one with nature, head back into town for a late lunch at Lardo. Here you’ll find scrumptious sandwiches like their classic porchetta or a more inventive ‘wich like the pho’rench dip which is a shaved beef sandwich dipped in Pho broth. Yum!Later, head to the biggest bookstore in the world: Powell’s. Literally taking up an entire block, Powell’s is known as the “city of books” and sells both new and used books. Powell’s is a Portland institution and a great way to spend an hour or two while you digest your lunch.
4:00 P.M. – GET HIGH
I know what you’re thinking, and while you will find your fair share of medical Cannabis clubs here, I’m actually talking about getting on the Portland Aerial Tram for some of the best views of the city. This tram regularly takes patients up to the OHSU hospital at the summit and only costs $4.55 for a round-trip! The 360-degree views are amazing, especially at sundown.
5:00 P.M. – DINNER A LA CART
Just as you exit the aerial tram, a food cart park awaits you in the Gantry Food Pod at the Zidell Yards. If it’s a rainy day and you don’t feel like eating outside, check out Portland’s indoor food cart park, Cartlab for a delicious and convenient dinner.
7:00 P.M. – TAX-FREE SHOP ‘TIL YOU DROP
One benefit of visiting Oregon is that, unlike California, it’s a tax-free state. So take advantage of the lower prices and get some shopping done on your trip. Portland and its neighbor Beaverton are home to Nike and Adidas. And while you’ll need to know a Nike employee to get you into their company store, there is a factory outlet you can go to for some great deals.
Pro tip: Gain access to the Adidas employee store by going to the Portland visitor center and getting a pass (good for up to five people). All you need to do is show your out-of-state I.D.
9:30 P.M. – ROOFTOP HOP
Now that you’ve spent some money with a little less guilt, head back to your hotel for a nightcap at their highly-rated rooftop restaurant, Altabira City Tavern.
9:00 a.m. – Where to Brunch?
It’s your last morning in Stumptown and you’ve got to go out with a bang. Start your day off with a delicious brunch. Pine State Biscuits has shrimp and grits, biscuits and gravy and a fried chicken sandwich–perfect for those looking for a hearty meal. You could also grab a boozy brunch at Tasty n Alder or Cheryl’s on 12th which are just around the corner from each other.
10:30 a.m. – Bike and Explore Washington Park
Portland is an extremely bike-friendly city, so rent some wheels and burn off some calories while you bike around town. There are many ride-sharing bikes on the streets, so renting is super easy. Once you’ve got your bike, make your way to Washington Park where you’ll need more than a few hours to explore.
Washington Park is home to the Portland Japanese Tea Garden which is one of the largest in the country at 5.5 acres. There are five separate gardens inside and you’ll definitely need to snap some photos for your Instagram while you’re there.
In addition to the beautiful tea garden, this park also houses the Oregon Zoo, Discovery Museum, International Rose Test Garden (when the roses are in bloom), Hoyt Arboretum, Portland Children’s Museum and more.
5:00 p.m. – The Last Meal
After you’ve biked and explored all over town, it’s time for your last meal in Portland. Le Pigeon’s food is a bit more upscale, but the food is worth the bill you’ll receive at the end of your meal. This acclaimed French restaurant has chef’s tasting options and dishes such as foie gras profiteroles, chicken cordon, and lamb tartare.
Pro tip: If Le Pigeon is booked, try their sister restaurant, Little Bird Bistro.
7:00 p.m. – Goodbye PDX!
It’s time to pack up, check out, and return your rental car. As you head home, you’ll most likely be planning your return trip and wondering why you don’t already live in Portland. Weird!