• Deschutes Brewery - Deschutes Brewery’s Portland Public House, which opened on May 2, 2008, is located in the historic 1919 G.G. Gerber Building in the Pearl District. This marks the brewery’s first expansion beyond its Bend roots and serves as a lively local gathering spot. Established in Bend in 1988 by Gary Fish and named after the Deschutes River, the company began as a community-focused brewpub, producing just 310 barrels in its first year. By the early 1990s, it had grown into a full-scale production brewery, gaining fame for flagship beers like Black Butte Porter and Mirror Pond Pale Ale. At the Portland location, patrons can enjoy core, seasonal, and experimental beers brewed onsite exclusively for this venue, all within a cozy, timber-accented space that combines Northwest charm with a Scottish pub feel.

• Al’s Den - Al’s Den is located underground, beneath a small flatiron building that originally opened in 1900 as a tire store and later served as a bathhouse. It offers a unique experience where guests can enjoy drinks, food, and music beneath the sidewalk, which still features the original 1900-era glass prisms that let light through. It is one of McMenamins’ 55 establishments across Oregon and Washington, many of which are housed in buildings listed on the National Register of Historic Places. McMenamins is Oregon’s oldest and largest microbrewery, known for a wide range of beers, but particularly for their Ruby, a raspberry shandy, as they were the first brewery in the US to legally use fruit in ales post-prohibition. Located in The West End, across from the now-closed Blitz-Weinhard Brewery, visitors can savor McMenamins’ beer in an underground setting that blends 1900s whimsy with a quirky psychedelic twist and a touch of steampunk.

• Powell’s City of Books - The world’s largest independent bookstore for new and used books.

• Portland Center Stage at The Armory - A Romanesque Revival armory annex built in 1891 to manage riots.

• Crystal Ballroom - Once a central hub for psychedelic culture, it features one of only three remaining floating dance floors in the US.

• Darcelle’s XV - Celebrating the legacy of the world’s oldest drag queen.

• Steel Bridge - The only dual independent lift bridge in the world.

• Lan Su Chinese Garden - Opened in 2000 as part of a cultural exchange with Portland’s sister city, Suzhou.

• Portland Oregon Sign - This iconic sign is situated on the former headquarters of White Stag Sportswear.

• Oregon Convention Center - Home to the world’s largest Foucault pendulum.

• Japanese American Historical Plaza - A memorial dedicated to the victims of internment camps.

• Ankeny Plaza - The site of Skidmore Fountain and the Saturday Market.

• Skidmore Fountain - Henry Weinhard once proposed running beer through this fountain.

• Kells Irish Restaurant & Pub - Kells is Portland’s leading Irish pub, offering traditional Irish beer, whiskey, and cuisine. The McAleese family opened Kells Irish Restaurant & Pub in 1990 in the historic Glisan Building, which was the last cast-iron building constructed in Portland in 1889. It is a prime example of Queen Anne Italianate cast-iron architecture. On this tour, guests can enjoy beer in an atmosphere reminiscent of Victorian Dublin, and they might even stick a dollar bill to the ceiling. After the tour, visitors can return to Kells independently to enjoy food and perhaps visit the underground cigar room, which was grandfathered in when smoking was banned in Oregon bars. Kells is more than just a pub and restaurant; both Kells and the Glisan building are iconic landmarks in Portland’s Skidmore/Old Town Historic District.

• Portland Saturday Market - Featuring handcrafted and locally made goods.

• Alcoholic beverages
• Local guide

• Gratuities (always appreciated)
• Food (please eat before tour)
• Transportation to/from start/end points

• Only Adult 21 years old and above are allowed on this tour
• Only Adults 21 years old and above are allowed on this tour

For a full refund, cancel at least 24 hours before the scheduled departure time.