The name Calloway is a boy's name of Latin origin meaning "pebbly place". Calloway and is often added to lists like Best Cool Unusual Boys' Names and discussed in our forums with posts like "Literary generation CAF".
From the experts:
Calloway is one of those irresistibly jaunty, animated three-syllable Irish surnames, like Sullivan and Finnegan--but this one has the added attraction of jazzy ties to the immortal "Dean of American Jive," Cab Calloway.
There was a 1951 comedy spoof called "Calloway Went Thataway."