Well I'm not getting lost in my own neighborhood the point was my range has gotten large enough to get out of my comfort zone, plus there is using my car to get me to different starting points.
I've ridden as far as Montreal, Philadelphia, and Rochester, riding no map, and just kind of winging it and keeping to a general direction.
This is what I'm talking about, I can't be in Rochester and be like "I ride in a general direction" for me that mean I'll wind up on the wrong side of one the finger lakes and have to do an extra 50 miles. To get back to your starting point or planned end point eventually you need to refine it more then "I ride in a general direction"
To tho OP, you're starting in the Bronx and there are a number of good routes that take you out to City Island or up to lower Westchester.
Don't forget Manhattan too, yes I have the trailheads to 3 major trails all within a 1.5 mile ride. Use them all the time