Henry Walter Webb Sr. (May 6, 1852 – June 18, 1900) was an American railway executive with the New York Central Railroad under Cornelius Vanderbilt and Chauncey Depew.

[1] While still an undergraduate, he participated in the Orton expedition that ascended the Amazon River almost to its source, and crossing the Andes, he exited South America by way of Peru, returning to the US by ship.

In 1893 he made a bold and ultimately true prediction for the next hundred years: By 1993, a traveler will be able to have his breakfast in New York City and his evening meal in Chicago.

[6] Webb lived in Scarborough, New York, was Show Chairman of the Westminster Kennel Club (1880–1882), subscriber to the Blackstone Memorial (1891), and helped dedicate a bronze statue of Christopher Columbus in Central Park (1894).

[8] In 1884, Webb married Leila Howard Griswold (1856–1910), and they had three children, two of whom survived to adulthood:[8] He died from heart trouble on June 18, 1900, at his country residence, Beechwood, in Scarborough, New York.