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St. Catharines is one of those cities that carries more history than its modest profile suggests. Loyalists arrived here in the 1780s after the American Revolution, and by the 1850s the city had become a significant terminus of the Underground Railroad. Harriet Tubman lived in St. Catharines from around 1851 to 1857, using it as her base while making multiple return trips south to guide people to freedom. At its peak roughly 800 of the town's 6,000 residents had escaped American slavery, a proportion that shaped the character of the place.

The Welland Canal, constructed between 1824 and 1833 to bypass Niagara Falls, made St.

Catharines the commercial hub of the Niagara Peninsula and remains a working engineering marvel. Montebello Park, designed by Frederick Law Olmsted in 1887, the same landscape architect who created Central Park in New York, blooms each spring with more than 1,300 rose bushes that helped earn the city its Garden City nickname. The Grape and Wine Festival each September draws over 100,000 visitors to a city that grows Niagara Peninsula varietals overlooked by better-marketed wine regions but taken seriously by those who know them.