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When was the first guide dog trained?

The first guide dog was trained at least as long ago as the middle ages and probably before that as evidenced by woodcuts depicting dogs guiding the blind.

The first modern guide dogs, what we now think of as guide dogs, were trained during and after WWI in response to the need for guides for soldiers blinded in the war.

"Buddy" the guide of Frank Morris was the first Seeing Eye dog, which was founded in 1929. The Seeing Eye is the oldest guide dog school still in operation.