Bert retired and then bought a ranch outside of Calgary in the 60's.
A nice aside from wiki:
Olmstead was inducted into the Hockey Hall of Fame in 1985. Olmstead, with his wife Nora, visited the town of Okotoks on August 13, 2005, with the Stanley Cup. He had previously declined to spend a day with it, believing that it was being given to much older winners only because of the lockout. Olmstead also noted, at the end of the day, that he was happy to have the Stanley Cup again.