Prince George Street was one of the original streets shown on early 1700s town surveys. The Middlesex County Courtyard backed up to the street, and the colonial Old Tavern still stands there today. Taverns, or ordinaries, were important to Middlesex's county street because on court days horse and buggy was the only transportation to town by land and sailing vessel by sea, so anyone coming any distance to court had to spend nights. In 1793 the town had only nine private dwellings but two taverns. Although the court restricted gaming in taverns, Urbanna, like most Tidewater Virginia communities of those times, had drinking and gaming, and the taverns offered card games, dice, backgammon, billiards, horse racing, cock fighting, sheeted beds, and a clean stall for the horse at night. Through the generations, it has been rumored that Virginia patriot Patrick Henry spent a night or two at Urbanna's Old Tavern. American patriot Dr. Arthur Lee of Lansdowne owned two lots on the street in 1790. A Methodist Church was built in 1902 on the corner of Prince George and Cross streets. Homes and buildings on the street today reflect a mixture of colonial, antebellum, Civil War, and post Civil War architecture.