The building at 288 Main Street in Danbury, facing Wooster Square, was once the home of the Danbury News and its famed publisher and editor, James Montgomery Bailey. Known as the “Danbury News Man,” Bailey gained national renown as a humorist and chronicler of local life. He was the author of such books as Life in Danbury: Being a Brief But Comprehensive Record of the Doings of a Remarkable People, Under More Remarkable Circumstances, and Chronicled in a Most Remarkable Manner (1873), The Danbury News Man’s Almanac, and Other Tales (1874), They All Do it: Or, Mr. Miggs of Danbury and His Neighbors (1877), The Danbury Boom!: With a Full Account of Mrs. Cobleigh’s Action Therein! Together with Many Other Interesting Phases in the Social and Domestic History of that Remarkable Village (1880), and the posthumously published History of Danbury, Conn., 1684-1896 (1896), compiled with additions by Susan Benedict Hill.
The building was originally a two-story Italianate Block, erected in 1873. Baily had it remodeled and enlarged in 1893, the year displayed on the structure‘s front facade. As redesigned by architect Philip Sunderland with a new front facade, third floor and tower, the Danbury News Building became a prominent landmark, widely identified with the city. It was once featured on the cover of the New Yorker. The Danbury News merged with the Danbury Times in 1933 and to form The News-Times.
Remarkably similar to the Bridgeport Post building:
https://historicbuildingsct.com/?p=10044
Very interesting comparison!