American cities and towns have always prided themselves on their grand avenues. The social elite and industrial captains often transformed normal thoroughfares into magnificent promenades lined with mansions to showcase their wealth. Post-Civil War America experienced a burst of this activity, but Rochester, America’s first true boomtown, had already set its sights on a grand avenue as early as 1840. The nouveau riche were anxious to establish a prestigious social colony befitting their stature. Using local and national architects, landscapers, and craftsmen, they transformed East Avenue from a crudely hacked pioneer lane into one of the grandest approaches to any city in the world. Although somewhat altered, it is still Rochester’s most beautiful street and remains one of Monroe County’s most spectacular features.