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As Portland’s top restaurants, coffee shops, and breweries migrate west toward Beaverton and Hillsboro, inner Southeast’s popular Wayfinder Beer is going east to the gateway of the Gorge. Wayfinder is the anchor of The Highlands, a glassy two-story food court and drink hall on the ridge of historic downtown Troutdale that soft-launched Aug. 3. Upon its grand opening celebration on Saturday, Aug. 31, The Highlands will serve as the new flagship location of pre-pandemic downtown Portland favorite Checkerboard Pizza.
Heavy metal, pagan, and gothic light-influenced Wayfinder Beer has been popular for its cutting-edge lagers and IPAs since it opened on the other side of the train tracks in the inner eastside Portland’s gritty Produce Row neighborhood in 2016. The flagship Wayfinder resembles a gated fortress carved in between the brick and rusting steel industrial remnants of Old Portland. With its second location, Wayfinder is going in the opposite direction without compromising what made it popular to begin with.
“Our pub in Southeast Portland is primarily a destination spot. While there are other great food and beverage options nearby, it’s not like walking down Division Street with multiple great choices in close proximity. I needed to find a location that wouldn’t cannibalize the pub’s sales,” says Wayfinder operations manager Annie Brix, who led the charge to reopen in Troutdale.
Brix found The Highlands’ location after overhearing a discussion on the redevelopment project and getting an impromptu tour of the former gladiola bulb processing facility. Brix, collaborating with The Highlands’ landlord, selected every light fixture, menu board, planter, plant, tile, paint color, trip, table and chair. It’s been a labor of love, she says. Despite not being a discovery brewpub location like Wayfinder’s flagship, it’s still run in the same spirit as the original beloved location.
The Highlands boasts a near-360-degree wraparound view of the Troutdale skyline. Wayfinder occupies a lower ground-level bar that serves signature cocktails, wine and non-alcoholic options, along with its fan-favorite beers. The taproom opens up into a beer garden surrounded by six food trucks, including Gyro King, Happy Sushi and Hawaiian-inspired Lulu. A roll-up door reveals Checkerboard Pizza in the back of The Highlands’ wood panel building. Additional suite will be occupied by tabletop shop Gone Gaming and Happy Cones, a Hawaiian ice cream scoop shop from Pittsburgh Steelers player Nate Herbig and Checkerboard co-owner Clint Bohling.
Wayfinder Beer co-founder Matt Jacobson is a hardcore pizza fanatic. He created the pizza chain Sizzle Pie, and sold it to Sortis Holdings in 2023 (WW has recently reported on Sortis Holdings’ and Sizzle Pie’s financial problems). But Jacobson couldn’t stay out of the pizza kitchen, and purchased Checkerboard, his favorite order-for-the-office pie spot. Created by master baker Ken Forkish of Ken’s Artisan Pizza, Checkerboard is an homage to the huge New York-style slices found only in the big city, but it was a pandemic victim when the downtown Portland food court Pine Street Market closed during COVID lockdown. Bohling and Jacobson kept the brand alive with a counter in Moda Center as they awaited The Highlands’ relaunch. Forkish remains a Checkerboard consultant.
“Ken has been a huge asset for me while refining the dough, which is a 72-hour ferment,” Bohling says. Jacobson describes Checkboard’s pies as “if you took Ken’s Artisan’s Neapolitan-style pizza and mashed it up with New York style, and used only the best ingredients possible.”
Brix, Jacobson, his go-to artist Orion Landau—who also works with Jacobson for the punk, metal and grindcore music label Relapse Records—and the rest of the Wayfinder team came up with The Highlands’ name and branding, and curated the food trucks and suites. The Highlands will host mini concerts at its grand opening party on Saturday, Aug. 31, which Landau says will run from noon to 10 pm. Hot Club du Jour will play a three hour set with guest vocalist Heather Lynn starting at 2 pm, followed by a music block by The County Champs starting at 6:30 pm.
On the surface, The Highlands seems a complete diversion from the original Wayfinder Beer location. But Brix was inspired by advice from her friend Tori George, who co-owns and operates One Moto Cafe and The One Moto Show.
“Her advice stuck with me: ‘Build a place in a location with the offerings you personally love, and the authenticity and charm of the place will prove itself true.’” Brix says. “I love Troutdale—the town has so much charm, the community is cool, laid-back, and friendly. It’s surrounded by some of the best hiking, camping, scenery, and views in the world, and it’s extremely dog friendly. It’s unpretentious, a little rough around the edges, and filled with good people—just like Wayfinder. I’m proud we can be part of that community now.”
GO: The Highlands, 105 SW 2nd Ave., Troutdale, thehighlandscarts.com. Noon–9 pm Monday–Friday, noon–10 pm Saturday–Sunday.