There are over 40 locations across British Columbia, Alberta, New Brunswick, Ontario, Nova Scotia, and Quebec.

The first Milestones location opened on Denman Street in Vancouver, British Columbia, in 1989.

In 2002, Cara (now known as Recipe Unlimited) purchased a majority stake in the restaurant from the previous parent company, BC-based Spectra Group, Inc.[1][2] Prior to Cara's acquisition, nearly all Milestones restaurants were located in British Columbia, with four locations in Ontario and one in Washington state.

[1] Cara rapidly expanded Milestones operations into Ontario cities, including Toronto, Ottawa, Niagara Falls, and London.

[3] On July 14, 2021, Montreal-based restaurant franchiser Foodtastic acquired Milestones.