Sunnyside was settled by homesteaders in the 1880's, and then incorporated into Calgary in 1904, Hillhurst was established in 1914. There used to be a street car that went down 2nd avenue to pick up CP Rail workers and then head east up to Centre street. The pathway that goes up the bank to the top of hill behind the Curling Club is where the street car used to travel.
This neighbourhood was primarily housing for rail workers, but by the 1920's, it was a growing neighbourhood that people used to call "The Bridge" – 14th street bridge wasn't built yet, so there was plenty of commerce and action on 10th Street between Memorial Drive and 2nd Avenue.
By the 1970's, the City of Calgary decided to develop the neighbourhoods into family-friendly communities, allocating more money for development of parking, playgrounds, new curbs, gutters and lanes, all through the the NIP (Neighbourhood Improvement Program).