Old Town's identity was forged in comedy clubs and preserved in Victorian architecture. The Second City, which opened on Wells Street in 1959, created the improv-to-SNL pipeline that has defined American comedy for sixty years, and the neighbourhood's bars and restaurants developed as the ecosystem around the stage — places where performers drank after shows and audiences continued the evening's energy. The Old Town Ale House, with its nude paintings of regulars and politicians, is the unofficial clubhouse.
The Victorian cottages and workers' houses that survived the Great Fire — Old Town sits just north of the fire's boundary — give the residential streets a European scale and domesticity. The Gold Coast, to the east, is old money: Astor Street's mansions, the lakefront promenade, Oak Street Beach at the foot of the Magnificent Mile. The two neighbourhoods share a geography but not a temperament — Old Town is theatrical and irreverent, the Gold Coast is polished and moneyed, and the blocks between them negotiate the difference with the pragmatism of a city that has always accommodated contradictions.