Established as a food cart in the 1940s, the brick and mortar restaurant has operated in the Goose Hollow neighborhood since 1947.

[3] The gastropub's[4] food menu features British[5] and Irish cuisine,[6][7] and has included burgers with truffle fries, a chicken Caesar salad, fish and chips with cod,[8] Guinness beef stew,[4] and shepherd's pie,[9] as well as beer, coffee, and wine.

[2] Brunch options include Belgian waffles, eggs Benedict, fried chicken, and rosemary-garlic biscuits and gravy,[8] with drinks like bloody marys and Irish coffee.

[16][17] Alex Frane and Thom Hilton recommended the Leaky Roof in Eater Portland's 2023 overview of restaurants in Goose Hollow.

[8] In 2024, Hilton and Maya MacEvoy included the business in an overview of "super-comforting" Irish food in the metropolitan area,[1] and Hilton and Brooke Jackson-Glidden included the Leaky Roof in an overview of restaurants near Providence Park "that are sure to score with" fans of the Portland Timbers.