If you’re spending the night in a former school or grabbing a pint in an old train station, the odds are good you might be headed to a **McMenamins**. This family-owned group of hotels, restaurants and brewpubs has won fans across Oregon since the 1980s. Its distinctive style — think equal parts Grateful Dead tour bus, retro brewpub, history museum and fanciful art exhibit — gives flair to every affordable stay and a little extra spice to every plate of crispy Cajun tots.

In 1983 brothers Mike and Brian McMenamin opened their very first bar, the **Barley Mill Pub**, in Southeast Portland. Over the next four decades, they opened 46 more properties across the state, ranging from tiny neighborhood watering holes to sprawling hotel complexes packed with unique gathering spaces. They launched two distilleries, a winery and a whopping two dozen breweries — many located in refurbished historic buildings — and commissioned thousands of pieces of artwork to adorn the walls. There’s even a podcast, **The Red Shed Tapes**, hosted by co-founder Mike’s daughter, Shannon McMenamin, that describes their colorful history.

“We started on this journey 40 years ago,” says marketing manager Renee Rank Ignacio. “Now the second generation is continuing on, and they have kids now, and their kids are talking about it.”

The properties are now considered an itinerary on their own, with their very own McMenamins **passport**, where visitors go to each location for stamps and a treasure hunt, yielding fun rewards like free hotel stays and merchandise. If you’d like to add some new brewpub stamps to your own book or stay for the first time at a historic hotel, here are a few ideas.

### Revisit Old School Days With a Cocktail in Hand

The main building of the **Old St. Francis School Hotel** in Bend, built in 1936, once housed a Catholic school. Today it’s a sprawling complex of fun, with a movie theater, an on-site pub and brewery, occasional live music and a jewel-like soaking pool surrounded by turquoise tile. Located in downtown Bend, you can stroll to parks and restaurants or just stay on campus, sipping cocktails in a space where kids once practiced their multiplication tables. **The Kennedy School Hotel** in Northeast Portland also offers the chance to play, dine and relax in a former elementary school, complete with an outdoor soaking pool, a theater and multiple tiny hidden bars.

Brews more your style? Order a pint at the **Barley Mill Pub **on Hawthorne Boulevard in Portland where you can find the place filled with eclectic decor, gathered from years of collecting the Grateful Dead memorabilia and other artwork and artifacts contributed from employees.

### Drink In History With Your Beer in Portland and Roseburg

When it was built in 1927, the **Bagdad Theater** on Hawthorne Boulevard was the largest theater in Portland outside of downtown and brought a serious dose of Hollywood glamour to town. Today it’s one of the city’s favorite spots to catch first-run flicks while enjoying a pint and some pizza. After the movie, decamp to the **Back Stage Bar** right around the corner for a game or two of pool.

If you’re planning to spend the weekend in Portland, consider booking a stay at one of the refurbished historic hotel properties, like the **White Eagle Saloon & Hotel** in North Portland or the **Crystal Hotel** — with popular music venue **Crystal Ballroom** next door — downtown. Or take a weekend getaway at McMenamins’ flagship **Edgefield Hotel** in Troutdale, a former county poorhouse on a 74-acre campus about 15 miles east of Portland. There you can visit the on-site brewery, distillery or winery, or just hang out in numerous small bars, some with fire pits. You’ll love the golf course, soaking pool and theater, too. The music offerings are legendary. Besides its onsite music venue, the property also hosts Edgefield Concerts on the Lawn every summer, featuring artists like Lizzo, Vampire Weekend and Young the Giant.

Located in an ornate 1912 train depot, the **Roseburg Station Pub & Brewery** in Roseburg pays homage to the glory days of the Southern Pacific rail line. The tap list includes McMenamins favorites like Ruby (a grapefruit-scented pale ale using Oregon-grown raspberries) and Hammerhead IPA (a classic West Coast IPA) or brewery-only ales like Spearhead Molly, an American brown ale named after the fictitious matron of the station. Savor the architectural details while you sip, including tongue-and-groove fir wainscoting, a nod to Roseburg’s history as a timber town.

### Golfing and Wine Tasting on the Coast and the Valley

Bustling McMinnville is a great home base for experiencing the Willamette Valley wine scene, and McMenamins’ **Hotel Oregon** is a fun, budget-friendly place to lay your head in the heart of all the action. Whether you opt for a room with en suite bathrooms or European-style digs with shared bathrooms down the hall, your lodging will feature a historical namesake from Oregon’s past, as well as a smattering of UFO-themed art in honor of a **1950 sighting** in nearby Sheridan, which generated some of the most famous images of UFOs ever taken. Grab a brew and a seat at the hotel’s rooftop bar to scan the skies.

The Coast boasts several bucket-list golf courses, including **Gearhart Golf Links**, which is one of the oldest courses west of the Mississippi. McMenamins’ **Gearhart Hotel**, established in 2012, sits right on the course, and guests get discounted greens fees. Non-golfers will appreciate the numerous options for on-site dining, loaner bikes, and the brief stroll across sand dunes to the beach. Fun fact: The bar top at the Sand Bar is made from a tree at McMenamins’ **Cornelius Pass Roadhouse** in Hillsboro, about 13 miles west of Portland, that was struck by lightning.