Via Miami History Now:
Dedicated in 1958, Kendall Drive began as a country road going through areas which were decidedly rural. Lack of development was such that when it was widened in 1964, the undertaking prompted a popular nickname for it: “The Road to Nowhere.” Today, it is one of the most travelled urban arteries in Miami-Dade County, with residential communities, malls and commercial operations of every sort lining its extensive progress.
Like its eponymous community, Kendall Drive is named for Henry John Boughton Kendall, a trustee of the Florida Land and Mortgage Company which purchased the tract of land now situated between Southwest 88th and Southwest 104th Streets in 1883. Henry Kendall managed the fruit groves set up by the company in the area. Southwest 88th Street, the road along the northern end of the holdings, began to be referred to as “North” Kendall Drive, although the application of the “North” component of the name is applied inconsistently along the road’s signage.