Tough Luck has been proudly serving fine cocktails and food in the Woodlawn Neighborhood since 2017 on our expansive wraparound patio and cozy indoor seating options.

Tough Luck is the largest bar from the same boozy bar folks that brought you The Old Gold, Paydirt, Hi-Top Tavern, and Holy Ghost. Located in a historic building in the Woodlawn Neighborhood of NE Portland, Tough Luck offers large and comfortable indoor seating options—complete with vintage shuffleboard—plus an incredibly large wraparound patio, much of which is covered and heated for your year round comfort. In addition to a robust food menu, we also have an extensive whiskey collection, ten local taps, creative cocktails and non-alcoholic options as well.

At Tough Luck Bar, we offer prizes for the top three teams each week.

Prizes can vary each week depending on the theme. The more you play with us, the more your points calculate up. The top three teams will receive an extra special gift at the end of the leaderboard period.

View the Leaderboard

Trivia at Tough Luck is on the 1st & 3rd Mondays of each month from 7-9 pm.

Tables are available on a first-come, first-serve basis, so show up early! Unfortunately, table reservations are unavailable at this time.

Tough Luck Bar is located at 1771 NE Dekum, Portland, OR 97211