Nestled in a tiny pocket of SW Portland is one of the most storied and long standing restaurants in town, The Leaky Roof. Sitting on the corner of SW16th and Jefferson, “The Roof” has been around for over 50 years, and is a staple in the Goose Hollow neighborhood.
Over time, it has progressed nicely from a rundown pub (hence the name) to an establishment that is known around the city for great food, a really great happy hour, and for having the largest collection of Irish whiskey in town. You can’t really go wrong in a place that serves a big burger and fries for $3 (also see McCormick and Schmicks). For $2.50 the quesadilla is another fantastic choice, and if you are feeling a little healthier, I would go for the chicken ceaser for 5 bucks.
While the Leaky Roof may be a little out of the way for many, I assure you it is worth the trip. Its the perfect place to enjoy a rainy day by their fireplace, enjoy some quality food, and sip on a wide array of Irish spirits. And I promise, the roof is no longer leaky.




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