In April 1754, a Port Royal FreeMason Fraternal chapter was established as the Kilwinning Port Royal Cross Lodge. Soon after the establishment of the lodge, within the 1750s, George Washington attended multiple Freemason meetings held at the homes of Captain John Micou, John Pearsons, Patrick Coutts, Robert Gilchrist, and William F. Gray. In addition, the lodge also met at Ann Fox’s Tavern, Dorthy Roy’s Tavern, Leonard George’s Tavern, and in the second floor room of William Hamilton Carter’s store, some of those locations which Washington is also believed to had been in attendance for. There was never a Masonic lodge building established in Port Royal and in the 1855 the Port Royal Masonic Chapter rented a room within a building that the newly formed Atlantic Lodge No. 2 was also using.

In 1881, the Port Royal Chapter of the Freemasons stopped having their meetings in Port Royal, after the Kilwinning Crosse Lodge, No. 2-237, A. F. & A. M. built in Bowling Green, Virginia. All of the Port Royal Chapter meetings were held in Bowling Green, Virginia were they still continue to this day. The Kilwinning Crosse Lodge is the oldest Masonic lodge in Caroline County, Virginia.