Five Portland Tour Companies Are Enhancing Our Love and Understanding of Portland

Consider adding some expert-level staycationing to your itinerary, which can be a perfect way to sightsee at home.

Peak Tours (Courtesy Heather Rose Pearson)

Rose City, Bridge City, Rip City, Stumptown. The list of Portland’s nicknames is long and charming—ever wonder where they all came from? Maybe you’re more interested in learning about the Shanghai Tunnels’ dark (and haunted) reputation. Or perhaps you’ve always been curious about the origins of those metal rings bolted to sidewalks across the city—you know, the ones with little plastic horses sometimes hitched to them?

Some of Portland’s most informative touring companies can provide information about all of these phenomena and more—and these guided journeys aren’t designed solely for out-of-towners. No matter your summer plans, consider adding some expert-level staycationing to your itinerary, which can be a perfect way to sightsee while on a budget.

Peak Tours and Transit

While cruising around in the Peak Tours van with host Damon Kupper, you’ll practically feel like you’re in a show on the Travel Channel. Kupper, a longtime theater professional, has been giving tours of Portland since 2005 and is what his partner Heather Rose Pearson describes as a “robust library of all things local.”

Thanks to Kupper’s even-keeled energy and encyclopedic knowledge of the city, spending a day learning about Portland is engaging and inspiring—and that’s the goal. When Kupper and Pearson founded Peak Tours and Transit, they wanted to create tours that weren’t just for people visiting Portland, but for those who live here, too.

“These aren’t just tours for tourists,” Pearson says, explaining that these excursions are about distilling the complex history of our city in an entertaining and inspiring way.

From learning about the individuals who helped shape Portland to understanding how the City Council was formed, Peak Tours aims to prompt Portlanders and tourists alike to keep asking questions. “There is a trajectory from the history,” Pearson says, “and if you know all that, you can kind of help shape it better.”

Peak offers a Touring Club for locals that meets the first Tuesday of every month, May through October, and plenty of other outings throughout the year. From wine and waterfall tours by van to downtown walking expeditions, Peak makes every journey feel unique and energizing.

Portland Ghosts

For those interested in creeping around the city after dark, Portland Ghosts offers elaborate walking tours, complete with rentable electromagnetic field detectors, of downtown’s notoriously haunted locations. The Rose City has long had a reputation as a paranormal hot spot due to local lore surrounding the Shanghai Tunnels and their alleged purpose to smuggle abducted men onto outbound ships, where they would be forced to work in the late 19th and early 20th centuries. Portland Ghosts takes visitors to a number of locations with ties to the subterranean passageway, including Kells Irish Pub and Old Town Pizza & Brewing—the latter of which is famous for its resident spirit Nina, whose name is carved into a brick in the old elevator shaft.

Portland Ghosts tours depart nightly; a standard outing includes eight stops and lasts about an hour, or you can opt for the extended edition of the walk with four additional locations over the course of 90 minutes. There is also a pub crawl version of the tour (drink prices not included) in case you need some liquid courage to confront Portland’s sordid past.

Architectural Heritage Center Walking Tours

Interested in architecture but don’t consider yourself an expert? The Architectural Heritage Center offers walking tours for those who appreciate structural design as well as Portland history and want to learn more.

“Many of our downtown tours and others in commercial areas provide an opportunity for us to show what was there prior to what we see today,” says education manager Val Ballestrem, who adds that guides bring old photos of buildings on the route so that tourgoers can compare past with present.

AHC offers more than 100 walking tours each year, the details of which are outlined on its website. And while there are several excursions that focus on the city’s core (Temples of Commerce Tour, Merchants & Markets Tour, West End), routes are not limited to downtown. AHC takes people through many different neighborhoods—from Buckman to Piedmont to the mazelike Ladd’s Addition. Many showcase how the landscape has changed, or been maintained, over time.

“As a historic preservation-minded nonprofit, our goal is to build public support for preserving our architecture,” Ballestrem says. “We hope that people come away from our tours with a better understanding of Portland-area history and architecture, and that even if they don’t like a particular architectural style, they learn enough to understand and appreciate it and can share what they’ve learned with others.”

Slabtown Tours

Come on any Slabtown Tours excursion and you’re bound to leave with a plethora of fun facts. Did you know the Slabtown neighborhood was once home to the largest artificial ice rink in the world? Or that an elephant marched next to two dump trucks at the 1931 dedication of the St. Johns Bridge? How about the oldest functioning flush toilet in town, which is more than 130 years old?

As owner and tour guide Tanya Lyn March puts it: “Our guided tours feel like a hybrid of a blind date and theater experience. The best tours are when strangers connect and engage each other and challenge the guide to go deep into their knowledge of Portland’s past.”

As its name would suggest, Slabtown does offer tours of outer Northwest Portland but also hosts walk-and-talks through Nob Hill and St. Johns. There’s even a Night With Ghosts outing that takes place in both Slabtown and Nob Hill, with a second planned haunted expedition in North Portland advertised on the company’s website.

Lost Plate Portland Food Carts, Pods & Patios Tour

Despite its inclement weather, Portland is known for its food carts. And we’ve been blessed with so many mobile kitchens, navigating the scene can be difficult—even for a local. Lost Plate guides are here to help, ushering you to some of the best carts in town.

The sagest advice is to arrive for your tour with an empty stomach. Attendees have the opportunity to eat a wide variety of cuisine—from Burma to Bavaria and beyond—as well as sample beers and desserts, with stops at two pods, a food hall and one brewery. In addition to all that eating, participants meet some of the chefs behind the food and learn about the history of Portland’s Central Eastside.

This story appeared as part of Oregon Summer, our annual free magazine out now all over Portland. See where to pick one up here.

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