Early Hartford grew up along the Connecticut River, with Main Street running parallel to the river's course. The major avenues originated in the late 18th and early 19th centuries as turnpikes, running out to the surrounding towns: Blue Hills Avenue to Granby, Maple Avenue to New Haven, Wethersfield Avenue to Wethersfield and Middletown, Farmington Avenue and Asylum Avenue to Farmington and Litchfield. Asylum Avenue, originally the Litchfield Turnpike, was renamed following the founding of the Asylum for the Deaf and Dumb in 1817. By Dudley's day, Farmington and Asylum Avenues were lined with Hartford's great insurance companies, while major industries were clustered along Capitol Avenue to the south and Windsor Avenue (now North Main Street) to the north.

In the 1920s, the maze of small streets between Front Street and the Connecticut River was a flourishing ethnic neighborhood with many small family-run shops and restaurants. These buildings were demolished in the 1960s to make way for Constitution Plaza.
Ref. # 1995.36.1025

The street in front of the exclusive Hotel Bond is still unpaved. Until 1920, the owners of the buildings abutting each street were partially responsible for the cost of improvements.
Ref. # 1995.36.1130

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Ref. # 1995.36.777