The Monticello Hotel, which opened at the corner of City Hall Avenue and Granby Street on September 27, 1898, was the largest and finest hotel in Norfolk for over 60 years. The hotel was built on filled land. By 1885 Town Back Creek had been filled to Granby Street. Construction of the hotel spurred additional development along the new City Hall Avenue. The hotel suffered a devastating fire on January 1, 1918. In addition to the flames, fire fighters had to deal with bitter cold and ice. When it reopened in 1919, two additional floors had been added, including a large dining room and horseshoe-shaped ballroom known in later years as the Starlight Room. This became a favored location for balls, dances, and community events. The grandly appointed mahogany bar doubled as a billiards parlor during Prohibition. During the 1933 hurricane, the hotel and broad area of downtown suffered considerable flood damage. The Monticello Hotel was the first building in Norfolk to be imploded in January 1976 to make way for the Norfolk Federal building now on this site.
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