Você pode usar um programa como rlwrap (wrapper readline) para isso:
rlwrap at now
Leitura adicional:
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hanslub42 / rlwrap (github)
* HOW TO USE IT: If $ <command> <args> doesn't let you use arrow keys to edit input, or if you just want decent input history and completion, try: $ rlwrap [-options] <command> <args>