Thomas Bailey Aldrich was born in 1836 in Portsmouth just a short distance down Court Street from the home of his grandfather, Thomas D. Bailey. Most of his youth was spent elsewhere, first in the South where his father had business, and later in New York City where he reached manhood. Between these two periods, Aldrich returned to Portsmouth to live for several years, from 1849 to 1852, with his grandfather in this house facing Court Street. 

Thomas Bailey Aldrich married Lilian Woodman in 1865, and they moved to Boston the same year. Aldrich quickly attained the friendship of such notables as William Dean Howells, Mark Twain, James T. Fields (another Portsmouth son), Henry Wadsworth Longfellow, and James Russell Lowell. He was recognized as a man of ability and accomplishment, and in time he succeeded Howells as editor of the Atlantic Monthly, the most important literary magazine of the time.

It was shortly after the move to Boston that Aldrich, aware of approaching fatherhood, began to record some thoughts on his own child hood. The result was The Story of a Bad Boy , a barely fictionalized recollection of adventures and impressions of his years spent in Portsmouth at his grandfather's house on Court Street.

Aldrich's idea for this children's story was new. While others wrote to instruct, his purpose was to entertain. "Tom Bailey" as he called himself, was no "faultless young gentleman," but rather "a real human boy such as you may meet anywhere." Among their exuberant adventures Tom and his friends set off some old cannons on the wharf at midnight, rousing the entire town, stole an old mail coach and pushed it into the Fourth of July bonfire, and spend a night "shipwrecked" on a river island.

Aldrich's Bad Boy is significant as the first realistic treatment of a boy in American literature. It had great influence on other writers including the author's close friend Mark Twain, who six years later wrote a similar story about a similar boy, also named Tom.

Thomas Bailey Aldrich died in 1907 at the age of 70. The house had passed out of the family by then and had in the 1880s served as Portsmouth's first hospital. It was repurchased by the Aldrich family and under the direction of Lilian Aldrich, the author's widow, the home was restored as a memorial to him. This was the first house in Portsmouth and one of the first in the country to be restored to a specific period in its past. Mark Twain was among those who journeyed to Portsmouth for the dedication. For seventy-one years the Thomas Bailey Aldrich Memorial Association opened the house to the public. In 1979 it became part of Strawbery Banke.