A convertible shelter system includes an enclosure having a removable side wall that selectively may be hinged to provide open access or to be held in an open position as a wind break. The convertible shelter system also includes the ability to fully remove the removable side wall on two enclosures having the same construction and to quickly and conveniently connect the remaining enclosure structures with a bridging panel, resulting in an enlarged, combined space while maintaining an essentially unobstructed ground surface.