Skip to content

10 Things No One Tells You About... Portland, Oregon

Oct. 22, 2016
7 min read
10 Things No One Tells You About... Portland, Oregon
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

Maybe you’re a fan of Portlandia or your curiosity has been piqued by the adage, “Keep Portland Weird." Either way, your tickets are booked and your bags are packed. Here are 10 tips for visiting Portland, Oregon, that you probably won’t find in a guidebook.

This City Truly Bares it All

As of late, Portland is best known for its hipster and crunchy (ie. extremely liberal and environmentally-friendly) behavior, but historically, the city is a shipping port with a strong affinity for strip clubs — in fact, it has the highest number of strip clubs per capita in the country. How does this claim to fame work with today's hipster crowd? One word: compromise. At Casa Diablo, for instance, only vegan food is served and strippers are only allowed to wear — er, remove— clothing that’s not made from animals. Fair enough!

Portlanders have lots of idea as to how to "Keep Portland Weird." Image courtesy of <a href="">Shutterstock</a>.
Portlanders have lots of idea as to how to "Keep Portland Weird." Image courtesy of Shutterstock.

In the Old Days, You Could Go to Sleep in Portland and Wake Up in China

Legend has it, old Portlanders used to kidnap drunks from those many strip clubs, ferry them through the tunnels of the city and force them to work as sailors on ships headed to China — an act known as "Shanghaiing." Now infamously known as the Shanghai Tunnels, the underground passages were initially intended to move goods from the ports to various locations throughout the city; now, many are supposedly haunted, but you’ll have to venture down there and find out for yourself, if you dare.

Shipping remains an important industry to Portland, but with a questionable past. Image courtesy of <a href="">Shutterstock</a>.
Shipping remains an important industry, but the tunnels once used for it have a questionable past. Image courtesy of Shutterstock.

Pinot Paradise is Closer Than You Think

On a lighter note, Portland is nestled in the Willamette Valley, a primarily Pinot-varietal, wine-producing region. The area may be lesser known compared to its neighboring California wine regions, but that doesn’t make visiting its vineyards any less worthy of your time. If you just have a day, plan to visit three wineries: start at Archery Summit Winery for its incredible vineyard views and high-quality Pinots, then make your way to Vista Hills Vineyard, a winery reminiscent of a mountain cabin crossed with a treehouse. Finally, head to the humble and welcoming Winter's Hill Estate Vineyard & Winery – it’s quieter than the others, which makes their pours just a little more precious.

A day at the vineyards is a perfect complement to your trip to Portland. Image courtesy of <a href="">Shutterstock</a>.
A day at the vineyards is an essential part of your trip to the Portland area. Image courtesy of Shutterstock.

It’s Always Wine O’Clock

If you don’t have enough time to head out to wine country, fear not! You can sample the region without leaving the city by visiting the Southeast Wine Collective, an urban winery and wine bar that serves a palate-pleasing sampling of Oregon’s finest wines. You can pop in for a flight and a cheese board or hear from a guest winemaker. Check out their robust events list to see what's going on when you visit.

Sign up for our daily newsletter
Taste the wines of Oregon right in the heart of Portland. Image courtesy of Southeast Wine Collective's <a href=";theater">Facebook page</a>.
Taste Oregon's best wines right in the heart of Portland. Image courtesy of Southeast Wine Collective's Facebook page.

Back to School Specials Aren't Just For Kids

If you’re looking for a different kind of drinking experience and a single malt and cigar are more your style, head to the Detention Bar at McMenamins. Like its neighboring Honors Bar and Theatre Bar, the Detention Bar is part of the former Kennedy School, now a complex consisting of restaurants, bars, a hotel, a movie theater and Concordia Brewery. Note that Detention Bar is just for the big kids (21+), but Portland's got plenty of family-friendly attractions as well.

This converted schoolhouse serves fun for all ages. Image courtesy of McMenamins Kennedy School's <a href=";theater">Facebook page</a>.
This converted schoolhouse serves up fun for big kids 21 and up. Image courtesy of McMenamins Kennedy School's Facebook page.

Nature is Never Too Far Away

Of course, there’s more to Oregon than fine wine and drinking establishments — namely, its proximity to the great outdoors. An hour’s drive outside the city offers a variety of outdoor activities, including windsurfing and kayaking in the Gorge, or my favorite: hiking. Even if you’re not an experienced hiker, there are plenty of novice-level trails available, with many of them offering stunning views of glacier-capped Mount Hood.

Explore the trails of Mount Hood. Image courtesy of <a href="">Shutterstock</a>.
Explore the scenic trails of Mount Hood about an hour from the city. Image courtesy of Shutterstock.

See New Life Spring From the Ashes

If you decide to take my advice on hiking, start at the Vista Ridge Trailhead, where you’ll wind your way through the desolate remains of the Dollar Lake Fire, a place where you'll find more than 6,300 acres of what I’ve dubbed a "graveyard of trees." In 2011, a lightning storm ignited the forest, and what remains is a spooky-yet-beautiful, otherworldly hiking experience. You'll see thousands of torched black and white trees standing above you, while new, colorful undergrowth thrives at your feet. It’s the circle of life, right before your eyes.

Left over desolation following the Dollar Lake Fire — now, a beautiful place to take a hike. Image courtesy of Shutterstock.

When in Doubt, Have a Great Cocktail

Now that you’ve worked up an appetite on your hike, head to Beast in Northeast Portland. The dinnertime wait can be pretty long but fortunately for patrons, its award-winning owner, Chef Naomi Pomeroy, opened the hand-crafted cocktail bar, Expatriate, across the street. Once you put your name in at Beast, head over to Expatriate and order a cocktail while you wait. The best part: they’ll know where to find you when your table is ready.

Hand-crafted cocktails at Expatriate are the best way to spend your wait for dinner at Beast. Image courtesy of Expatriate's <a href=";theater">Facebook page.</a>
Hand-crafted cocktails at Expatriate are a must before your dinner at Beast. Image courtesy of Expatriate's Facebook page.

Where to Find the Best Phở

If Asian cuisine is more your style, skip trendy Pok Pok and head to Luc Lac. This Vietnamese kitchen serves up a simple-yet-unique dining experience, so don't be turned off by the line coming out the door. Here, you order at the counter — your drinks are delivered to you while you wait — and once a table is ready, you can sit and enjoy the phở-nomenal Asian cuisine this place is known for. It's a cool dining concept, and an even cooler spot to nosh on all your Vietnamese favorites.

Head over to Luc Lac for authentic Vietnamese cuisine. Image courtesy of Luc Lac's Facebook page.

Support Local Artists at the Portland Saturday Market

Looking to pick up a souvenir on your way out of town? Swing by the Saturday Market and visit the kiosks of hundreds of local artists, jewelry-makers, and chefs. A bite from a local food truck and a print of the iconic “Made in Oregon” sign will be the perfect way to wrap up your visit to this Pacific Northwest gem of a city.

Shop from local artists at the Portland Saturday Market. Image courtesy of Shutterstock.

Have you ever been to Portland, Oregon? What are your favorite things to do there?

Featured image by Portland, Oregon, at night. Image courtesy of Shutterstock.