Gregory is one of the original town sites established by the opening of the Rosebud Reservations in 1904. Houses sprung up over night and Gregory has continued to be a thriving town. No, your eyes are not playing tricks on you there is an actual, still operating drive-in movie theater on the outskirts of town. Gregory has one of the few remaining Drive-In Theatres in the U.S. The larger than life pheasant sitting in Gregory Park is a symbol of the fact Gregory sets in prime pheasant hunting country. The wily pheasant has become a major income factor for many of the local ranchers. The natives here “brake” for pheasants, so drive slowly and carefully, enjoying the beautiful prairie vistas and the wildlife. Gregory is definitely a must stop place along this Trail.