adverb (or adjective)
1. also upon the town : supported by poor relief provided by the town or parish : destitute
a family on the town after the father's death
2. : in carefree and often roving rollicking pursuit of the pleasures and diversions available (as in the night life of a big city) often in a spirit of welcome relief or abandon after a period of constraint or routine : out for a good time : footloose and fancy-free
hired a baby-sitter and went out on the town
a bunch of sailors on the town — Maxwell Griffith
had decided to go out on the town … to all the dives — Dawn Powell