The best way to do this is with several trail cameras, and good maps/aerial photos.
Step 1: is to determine the direction of his entry, either by the direction he faces in the pictures or by ringing the field in cams and learning which ones he uses.
Step 2: is to start to make some assumptions on distance from bedding to your food source based on time of night. You mentioned 11pm, so it could be a LONG ways respectively.
Step 3: With him possibly far out there, I would place cameras on trails that lead to your field where they intersect your property line and try to narrow down which one he frequents. Based on the time he tends to pass those camera locations, you should know if you are in the ballpark. If you can acquire access further than your property line, you keep spreading out in each direction.