The first Pickle Barrel opened in 1971 as an 85-seat restaurant located on Leslie Street in Toronto.

[1] Over the subsequent decades, the restaurant expanded to become a chain with locations across the Greater Toronto Area (GTA).

[1] On October 16, 2017, The Pickle Barrel was acquired by Cara Operations Limited (renamed Recipe Unlimited in 2018), a subsidiary of the holding company Fairfax Financial.

[1] blogTO noted that the restaurant is "known for its lengthy menu and kitschy decor",[5] including colorful leather booths and blown glass hanging lights.

[6] In September 2022, the Pickle Barrel at Sherway Gardens in Etobicoke closed permanently.