Portland, Oregon

A weekend in Portland has been on my travel bucket list for as long as I can remember. I should clarify, seeing Multnomah Falls, the most visited natural recreation site in the Pacific Northwest is what was on my bucket list. Experiencing Portland was a bonus.

If Portland lands itself on your list, here are my top suggestions.

Stay at the Duniway in downtown Portland.

The Duniway in downtown Portland

Just 30 minutes from the PDX Airport, the Duniway is a landmark. Once you arrive, you’ll see why I chose it. Velvet wallpaper, loft-style floor-to-ceiling windows, plush pillows, eclectic furniture, and modern art – the Duniway will have you feeling like you stepped into a different life. One where you are far cooler than you have ever been – or ever will be. This place is also often called out as a favorite wedding venue, and it’s true! I bumped into the most elegant bride I have ever seen when I was walking through the lobby on my way to Pioneer Courthouse Square.

Milepost at Pioneer Courthouse Square

Speaking of Pioneer Courthouse Square, its right around the corner from the hotel. Also known as Portland’s living room, the Pioneer Courthouse Square is a public space in the center of downtown.  Opened in 1984, the square is named after the Pioneer Courthouse, an 1875 federal building occupying the block directly adjacent. It was originally the site for a school. Later becoming the eight-story Portland Hotel in 1890. The hotel was the center of the city’s social activity for the first half of the 20th century. One of the original archways and gate work from the hotel were made part of the urban design and can be found on the east side of the square.  I love the way the entire park is set up much like an amphitheater, with the whole of Portland on display for your viewing pleasure.

A local ale from a vendor at the Portland Saturday Market

After you are done at the square and if staying outdoors is in the cards, head to the waterfront where you’ll find the Portland Saturday Market. Don’t worry, contrary to the name, they are open on Sunday’s, too. This market is the largest continuously operated outdoor market in the United States, operating from March through December 24. It is a blast. Situated adjacent to the Willamette River, the market is filled with over 200 booths where you can find artisan soaps, wall décor, local beer, live music, and a cornucopia of food trucks. I can’t hype this enough – it is the place to be!

Voodoo Doughnuts marquee

If you haven’t filled up on the smorgasbord of endless options the food trucks have to offer, go find Voodoo Doughnuts. It is a matchless, quirky doughnut shop where you’ll find silly creative donuts like Memphis Mafia, a fried doughnut with banana chunks and cinnamon covered in glaze, drizzled in chocolate and peanut butter with peanuts and chocolate chips on top, the Gay Bar, a raised yeast doughnut chock full of luscious Bavarian cream and topped with vanilla frosting and all the colors of the rainbow, or the Diablos Rex, a chocolate cake doughnut with chocolate frosting, red sprinkles, a vanilla frosting pentagram, and chocolate chips in the middle.

Interior of Voodoo

Voodoo’s tour de force is the Voodoo Doll. It is a raised yeast doughnut shaped like a ghost with arms, filled with raspberry jelly (think blood), topped with chocolate frosting and to top it off, stabbed with a pretzel. Not going to lie, I bought two – just to say I did it. 

Dante’s Live Music parking lot

Also, don’t forget to head to Dante’s Live Music, across from Voodoo to get a shot of their sign.

The White Stag sign

Keeping with the iconic stops, make your way to the White Stag sign. The White Stag sign, also known as the “Portland Oregon” sign, is a lighted neon-and-incandescent-bulb sign located atop the White Stag Building, at 70 NW Couch Street in downtown Portland. Installed in the 40s, it has since become a Portland landmark.

Next, and hopefully, by now you’ve worked up an appetite, go to Huber’s, just to get the Spanish coffee. Huber’s is Portland’s oldest restaurant having been established in 1879 at the corner of 1st and Morrison downtown.

The Bar at Huber’s, Portland’s Oldest Restaurant

Interestingly, it was originally called “The Bureau Saloon” until it was purchased by Mr. Frank Huber changing the name to his likeness. Don’t let the unsuspecting curbside fool you, Huber’s is as close to a speakeasy as I have ever been with its round-the-back-down-the-hall-wink-at-Mitzy-and-knock-three-times feel. Why the Spanish coffee, you ask? Well, they make it tableside. The waiters take years to learn the presentation and it is worth it. Kahlua, Cruzan 151, Bols triple sec, and coffee topped with fresh whipped cream and nutmeg. Bravura.

Deschutes Brewery and Public House

Next is Deschutes Brewery for a burger. No, really. The Portland brewery is combined with the Portland Public House, an upscale lumberjack-meets-urban restaurant, which is really what matters here. Feast on the Brewery Board that comes complete with Obsidian Stout salami and cured meats, Face Rock Creamery Black Butte Porter Cheddar, Briar Rose Creamery Freya, breads, fruits, pickled vegetables and then, your stomach willing, order the pièce de résistance, Pub Burger – two quarter-pound Oregon Valley Natural grass-fed beef patties, fry sauce, cheddar, lettuce, red onion, and beer-brined pickles. It is a sight to behold, ladies and gentlemen.

The only empty hall at Powell’s

Not too far from Deschutes is Powell’s City of Books. A legend in the world of booksellers, Powell’s is thriving. There is not only a line out every entrance door (there are several because the place occupies an entire city block), but the halls are filled to the brim with people. It is incredible to see so many people finding so much excitement over the written word. There are nine color-coded rooms and over 3,500 different sections you can dig through. From Tolstoy to Faulker, from Orwell to Hemingway, from Burroughs to Strayed, you can find what you are looking for at Powell’s.

Rows of pinball machines at Ground Kontrol

Once you are done pursuing the stacks at Powell’s, get yourself over to Ground Kontrol, the coolest classic arcade I have ever seen. Considered the largest and best-maintained public game room in the Pacific Northwest, the dark walled joint is full of more than 90 of the best arcade games and original video games in their original cabinets and gameplan, including even the original quarter slots! Ground Kontrol hosts several other things like competitions, comedy shows, and has DJs. There is even a full bar, I kid you not. It is open until 2 am, making it a great place to go when you have run out of ideas.

The PORTLAND marquee at the Arlene Schnitzer Concert Hall

Speaking of things to do at night, don’t forget to stop by the Arlene Schnitzer Concert Hall to snap a picture of the PORTLAND marquee. Built in 1928, it was originally the Portland Public Theatre but later renamed the Paramount Theatre. It is one of the last surviving theater venues on Broadway. The Concert Hall plays host to a variety of presentations including classical, jazz, pop, rock, folk and gospel music, dance, theatre, travel films, conferences, and weddings. To be honest, I had to see it for the pizzazz and glamour.

Portland Art Museum gallery

If you are a museum or art fan, you can’t go to Portland without checking out the Portland Art Museum, the oldest art museum in the Pacific Northwest and seventh oldest in the United States. It is incredible. Founded in late 1892, the art museum was originally located in the public library. By 1905, the Museum had outgrown its location and moved into a larger space.  The first exhibition in the new building featured watercolors and paintings from the 1905 Lewis & Clark Exposition, which was held in Portland.

Modern American art gallery at the Portland Art Museum

In late 1913, the Museum hosted one of its most important early exhibitions. The exhibition featured artwork that had been on display earlier that year at the famous 1913 New York Armory Show, which introduced American audiences to Modern art.

Modern Art installation at the Portland Art Museum

Quickly growing in size and notoriety, the museum has since expanded several times to continue to take on massive collections. So, of course you have to see it. The most notable pieces I saw were Waterlillies by Claude Monet and The Ox-Cart by Vincent Van Gogh. I gush.

All that walking around certainly grows your appetite. Head over to the Virginia Café for a drink before calling it a day. The Virginia Café was first opened in 1914.  This is the point in the weekend, I would strongly recommend taking a break to recharge, because an adventure awaits.

Jackrabbit, the Duniway Hotel Restaurant and Bar #JACKRABBITPDX

Begin the morning with breakfast at the hotel. Whether you are in the area for a business meeting or to hike the Columbia River Gorge (which is exactly where you are headed!), Jackrabbit will have what you need. Touting a host of accolades like Best New Restaurant in 2018, Jackrabbit gives you all sorts of reasons to take a seat. I endorse the Duniway’s signature sandwich that comes with soft scramble, bacon, and smoked cheddar. A perfect way to start the day, 

View of mountain top of Columbia River Gorge

Next, drive out of the city. Head toward the Dalles for about 30 minutes. You’ll know you found Multnomah Falls well before the sign ushering you off the highway, I promise.  Multnomah Falls is the highest waterfall in the state of Oregon, and second highest year-round waterfall in the nation. The upper falls drops 542 feet and the lower falls another 69. The water is supplied by natural underground springs that originate on Larch Mountain, an extinct volcano. Interesting fact; according to Native American lore, Multnomah Falls was the site where a tribal princess threw herself over the falls to save her tribe from a dreadful illness.  

Benson Bridge at Multnomah Falls

You can park next to the Multnomah Falls Lodge or across the street and take the underground tunnel to see the falls unobstructed. Do this – it is magnificent up close. From the overlook, you can see the base of the lower falls. Make sure to walk the quarter mile trail to Benson Bridge. The 1914 bridge allows you to cross over and get a steamy view of the lower falls. The spray from the waterfall creates a colder micro-climate so plan to dress warm.  If you are really brave, you can hike another mile up the slick, misty path to the viewing platform at the top of the falls. I have to say, I am not that brave.

What better way to decompress from the excitement of getting sprayed by a waterfall than to hang out by the fire?  Head to the base of the falls to get to Multnomah Falls Lodge. Built in 1925, the gorgeous cottage style restaurant is made of every type of rock found in the gorge. The restaurant is worth staying for. They serve upscale, Northwest cuisine in an atrium-style comfortable and casual atmosphere. It is perfect for a hearty pre- or post- hike breakfast, home-style comfort foods to warm up with, or a romantic dinner in front of the fireplace.

View of the Bridge of the Gods from the Oregon side

When you are ready to go back to the city, do yourself a favor and drive another 15 minutes further east. You will be able to cross the Columbia River via the Bridge of the Gods. This connects Cascade Locks, Oregon, and Washington near North Bonneville, meaning you can drive the coast of Oregon to get there and the coast of Washington to get back!   Interesting fact; In September 1927, onlookers saw Charles Lindbergh fly the Spirit of St. Louis from Portland low over the (new at the time) bridge and then make a 180 degree turn and fly back under the bridge, continuing to the Portland Airport.

Named after the historic geologic feature also known as Bridge of the Gods, the bridge sits at the convergence of The Historic Columbia River Highway State Trail, three National Historic Trails, and the lowest point on the Pacific Crest Trail. The bridge, as well as the Pacific Crest Trail, were made famous by Cheryl Strayed’s 2012 book Wild where her journey on the PCT concluded with her making it to the bridge. The book details an incredibly painful point in the author’s life that led to a much needed pilgrimage. The bridge has since been a beacon to those traveling through travails. I felt much the same way when I crossed it.

The Columbia River Gorge

As you drive the ~40 miles back to Portland, be sure to take in the inexpressibly awe-inspiring Columbia River Gorge. The river winds westward through the Cascade Range, forming the boundary between the state of Washington to the north and Oregon to the south. The canyon itself stretches for over eighty miles and is up to 4,000 feet deep. The area is known for its high concentration of waterfalls, with over 90 on the Oregon side of the gorge alone. It has a huge range of elevation and precipitation making it an extremely diverse place that is a popular destination for just about everything from hiking, biking, and sightseeing, fishing, and water sports.

Cape Horn

My favorite part of the gorge – Cape Horn. The Cape Horn trail is one of the closest of the gorge trails to the Portland-Vancouver metropolitan area. The trail gives you some of the most incredible views of the river along with rocky cliffs, vast valleys, foliage, and even a waterfall. If you follow Cape Horn Trail for two miles, you can get to the Cape Horn Overlook. This view alone makes the entire trip worth it.

Whether you are all-in, or one to pick and choose, Portland is worth the experience. For an easy recap, save your very own Portland, Oregon Bucket List below.