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What does this phrase actually mean? Where is it from?

I hear it a lot in songs and on TV shows etc....

"One if by land, two if by sea"
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It describes the signaling that patriots in Boston used to forward the news of British soldiers arriving in April 1775.

some details here: https://www.oldnorth.com/our-history/

That wording was used in a famous poem called Paul Revere’s Ride.

https://poets.org/poem/paul-reveres-ride