Did you know this dome-shaped building is one of the last remaining structures from the Lewis and Clark Exposition in 1905? Barged down the Willamette River to its current location, the former exhibit hall is now one of McMenamins’ most quirky theater pubs.

If you’ve ever fantasied about sipping cocktails in detention, this transformed elementary school provides just that. The sprawling venue has three restaurants, two bars, a second-run movie theater, live music events, a soaking pool, and guest rooms. Don’t miss the Boiler Room Bar for some elaborate metal artworks.

Before it was a go-to spot for the North Piedmont neighborhood, the Chapel Pub was a mortuary lauded as one of Portland’s finest architectural specimens in the early 1930s. Look for the mahogany-wood, tugboat-shaped bar, the intricate ironwork, and central chandelier — all fashioned by master craftsmen.

Built in 1905 as a watering hole for Polish immigrants, the White Eagle is one of the last echoes of Old Portland’s working class history, as well as its rock ‘n roll counterculture of the ‘70s and ‘80s. Look for the original oak back-bar, ceramic-tiled floors, and the corner stage where rock and blues legends have performed for decades. The spot also comes with some pretty great ghost stories.

Originally the county poor farm, this 74-acre property is located at the mouth of the Columbia River Gorge, with 10 restaurants and bars, extensive murals and artwork, a movie theater, a distillery, a winery, a brewery, the popular Summer Concerts on the Lawn series, and an on-site glass-blower. Black Rabbit Restaurant is where you’ll find some of McMenamins’ more innovative dishes, like slow-cooked wild boar or seared tuna with nori risotto cake.

Portland’s original cheap theater, the 150-year-old Mission is still one of the best — and most affordable — places in town to grab dinner and drinks while watching a second-run movie on the big screen. 

Once the jewel in dance hall king Montrose Ringler’s crown, the Crystal is now a multi-block complex on West Burnside Street that includes Ringlers Pub, Crystal Brewery, the Crystal Hotel, Zeus Cafe, and the subterranean bar, Ringlers Annex. Look for house cocktails, seasonal beer specials, and lots of live performances.

The font from which the McMenamins empire sprung, the Barley Mill is like a 1980s Portland time capsule: charmingly eclectic, a little weird, and obsessed with the Grateful Dead. The menu includes sandwiches, burgers, and salads. Be sure to check out its namesake mill and all the original murals painted by Norm Forsberg and Joe Cotter. 

Of the 25 breweries McMenamins operates, this is the one to visit, because it’s often brewing experimental batches and other small-production runs. And when you’re tucked into a cozy wooden booth at this unassuming pub, don’t forget that you’re inside a slice of Oregon beer history: In 1985, Hillsdale became the first brewpub operating in the state since Prohibition. It’s also the birthplace of the signature Hammerhead, Ruby, and Terminator beers.