The Twilight Zone SE04-EP14 (1963)

"Of Late I Think of Cliffordville"
In this episode, a wealthy and jaded businessman, William J. Feathersmith, yearns to relive the thrill of building his fortune from scratch. He strikes a deal with a mysterious travel agent, Miss Devlin, to return to his hometown of Cliffordville in the year 1910, retaining his memories and youthful appearance. However, he soon discovers that the past isn't as he remembered, and his knowledge of the future doesn't guarantee success.
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