The area was most likely first named for Maiden's Adventure Farm, a nearby estate mentioned in the 1755 will of John Fleming. By 1824, construction of the James River and Kanawha Canal had reached Maidens Adventure, and in 1825 the Maidens Adventure Dam was built to raise the water levels of the James River. Cliffs along the upper side of the James prevented building a towpath and canal there, so the dam created a pond about four miles long and the towpath followed the shoreline along the upper side of the pond. After the railroad arrived in 1880, the Maidens Adventure Hotel was built to serve passengers on the Richmond and Alleghany Railroad. The William Tucker family bought and operated the hotel, a general store, and a post office in 1896. The first bridge across the James River at this location was built in 1914. Maidens is now primarily recognized as a post office serving addresses in three counties.