If the graceless expanse of City Hall seems like an eyesore in comparison with the colonial coziness of Faneuil Hall, it's not for lack of architectural ambition. When Boston resolved to replace Scollay Square (a seedy "sailor's paradise" teeming with gambling dens, tattoo parlors, shooting galleries and strip clubs) with a professional complex called Government Center, the city hired the celebrated firm of I.M. Pei and Associates to engineer the transformation. A disciple of Walter Gropius, Pei was inspired by the challenge of harmonizing gargantuan new structures with the comparatively quaint historic buildings of the neighborhood. Though City Hall was to be the centerpiece of Pei's vision, its design was delegated to the firm of Kallman, McKimmel and Knowles, who won a national competition with their plans for a monumental structure, to be built in a style aptly known as Brutalist Modern.

While some welcomed the new City Hall on its 1968 debut, its contemporary critics include Thomas Menino, who regularly refers to his workplace as "ugly") and erstwhile former mayor John Collins (under whose administration the contracts were awarded), who once admitted to a reporter that "a few light bulbs and some soap and water would help." Despite the Kafka-esque oppressiveness of its appearance, City Hall Plaza is the center of Boston's celebration calendar, hosting concerts, festivals and a farmer's market in summer, and the ever-popular Enchanted Village during the winter holidays. -- Julia Clinger