i used to ride all different routes for a few years but now doing the same thing well that's pretty normal to me. i've started to go into the city 3 days a week and I do the same ride every time on the bicycle greenway. 15 miles total. flying solo and as fast as i can.
here and then i'll make a little adventure venturing into the city streets to go try a new restaurant or food stand/establishment.
lastly when I manage to convince a friend or acquaintance or two to ride then we partially ride the same greenway but then go off it and do some exploring. unfortunately while i love riding with a couple of other people and exploring with them, it doesn't happen enough. maybe i'll find a nyc meetup biking group. that's a thought. though any group over 5 or so just feels like it will get unwieldy in city traffic.
but pretty much it's that same route almost all the time and its very rewarding.
do you live near a major urban area or more suburban/rural?