
2 hours
Portland: Mystery Paint & Sip Night at a Trendy Brewery
Join a fun mystery paint & sip night at a local Portland brewery. Cold drinks, brushes and a surprise painting revealed on the night, no experience needed, just show u...
Radio Room is a rooftop bar in Alberta Arts District, Portland.
Editorially verified May 20, 2026 by Elliot Marsh, TableJourney editor. Source.

2 hours
Join a fun mystery paint & sip night at a local Portland brewery. Cold drinks, brushes and a surprise painting revealed on the night, no experience needed, just show u...

Guided tour · 3 hours
Find out what the food cart hype is about in the food cart capital of the world. On this walking tour you'll discover global food & drinks, and learn fun history in th...

Guided tour · 2.5 hours
Walk around the bustling streets of Downtown Portland with your local guide and discover why Portland is the coffee and donut capital of the world.
Tip: The roof has its own bar and stays open seven days; the fireplace half stays warm in shoulder season, the open half is the sunset perch in summer.
Address: 1101 NE Alberta St, Portland, OR 97211
The Multnomah Whiskey Library is the second-floor gentlemen's-club-style room on SW Alder where the back wall holds more than 1,500 spirits, with whiskey carts rolled to the table.
TipWalk-in waits can run two hours on weekends; the membership line and the public line move separately, so book a member's reservation slot if you can.
Teardrop Lounge is the corner cocktail bar in the Pearl that has been pouring fresh-pressed daiquiris and house-tinctured stirred drinks since 2007, with a horseshoe bar and street-level seating.
TipHappy hour runs 16:00-19:00 weekdays; book the bar via Resy if you want a stool, the floor takes walk-ins.
The Driftwood Room is the vintage cocktail lounge inside Hotel deLuxe on SW 15th, open since 1954 with curved black-leather banquettes and a Manhattan flight on the menu.
TipOpen seven nights from 16:00; bar seating goes first, the booths are walk-in and stay quieter through the early shift.
2NW5 is the basement cocktail bar in the Hoxton Hotel, a concealed Old Town room with antique furnishings, coastal Mexican plates from Chef Adan Fausto and classic cocktails.
TipEntrance is through the Hoxton lobby; bar reservations help on Friday and Saturday, walk-in stools open up on weeknights.
CC Slaughters is the longstanding Old Town dance club on NW Davis that has anchored Portland's queer nightlife since 1981, with a no-cover door, a big floor and live DJs Thursday through Saturday.
TipLate-shift weekends run to 02:00; Sunday opens at 14:00 with day-drinking and karaoke. New ownership took over in 2025 after a brief closure scare.
Silverado is the two-level Old Town gay bar that ran for decades in the Burnside Triangle and relocated to NW Couch in 2018, with a basement dance floor and male dancers and a quieter ground-floor bar.
TipUpstairs is the daytime bar with food; downstairs goes late on weekends with go-go dancers and a small cover.