Industrial, dark and vast, Central Eastside and Inner Southeast present both rugged and refined happy hour options. Whether it’s a winery, outdoor-obsessed brewery, neighborhood bar, or swanky cocktails you seek, you’ll find them in this often overlooked area of Portland. When the clock strikes five, check out these drinking establishments for the best deals and most charismatic surroundings.

 

Biwa: With two happy hours (5-6:30 PM and late night from 9-10 PM) and $1-$4 appetizers, Biwa is a must-hit on an inner Southeast drinking excursion. Start out with a Japanese chuhai (a low-proof cocktail) to ensure longevity and pound some rice balls for an optimal absorption rate. (215 SE 9th St.; 503-239-8830). 

 

Cyril’s at Clay Pigeon Winery: The mashup of Sasha Davies’ background as a cheese enthusiast/monger and Michael Claypool’s experience in the wine industry are the backbone of the tasting room and cheese bar at Clay Pigeon Winery. During happy hour, glasses of house red or white wine are $5 and with a glass of HH vino, you’ll get half off ala carte cheese regularly $6 (815 SE Oak St.; 503-206-7862).

 

Base Camp Brewing: Equally drool-inducing beer and decor are the norm at this outdoor-centric brewery. During the week catch deals from 3-6 PM or all day on Mondays. In addition to exceptional beers and happy hour prices ($1 off pints), the brewery also offers outdoor classes, movie screenings, live music, and trivia. Food available from Pizza Box and Gonzo food carts (930 SE Oak St.; 503-477-7479).

 

The High Dive: Neighborhood bar vibes meet beautiful pine and artwork covered walls at The High Dive. We didn’t have to search for the “dive” in this place for very long; On our visit there was a tag in the bathroom warning patrons not to mess with the bartender. Jello shots, S.I.N. all night, every night, and a happy hour that lasts from 4-7 PM earns The High Dive a spot on the top of the list for best happy hours in town (1406 SE 12th Ave.; 503-384-2285).

 

Rum Club: When it comes to creating a lasting impression, the Rum Club prevails with dashes of orange bitters, splashes of Demerara syrup, and drops of grapefruit oil. Happy hour lasts from 4-6:30 PM and entails $6 elixirs with the chance of a celebrity bartender spotting (720 SE Sandy Blvd.; 503-467-2469).

 

Bunk Bar: Finish up your crawl with a show in the industrial area on Water Avenue at Bunk Bar. Utilize a Meatball Parmigiano Hero or the Mole Tots to soak up the booze. Expect a cover charge, even during the week to see bands tear it up in front of a mural of Harry Dean Stanton (1028 SE Water Ave.; 503-477-9515).