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 "Baby a Day".
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."