Almost as soon as the Trans-Allegheny pioneers had settled along the navigable rivers, some type of entertainment was offered from barges or flatboats. Noah Ludlow was one of the earliest to bring professional actors and musicians to the frontier. In 1816, he bought a 25-foot flatboat with a small shelter at Olean, New York, on the Allegheny River. He named it Ludlow's Noah's Ark and with 11 associates floated down the Allegheny, Ohio, and Mississippi rivers, stopping to perform wherever they could.

Beginning in the 1830s, showboats regularly appeared on the inland rivers. William Chapman Sr., an Englishman, was the first person to purposely plan and build a showboat for use on the western rivers. His Chapman Floating Theater floated down the Ohio River from Pittsburgh in 1831. This was the first of many family showboats. In 1836, Chapman acquired a small steamboat to tow the Floating Theater upstream, rather than selling the showboat at New Orleans as had been the practice in years past. With this new means of moving from place to place Chapman could also travel up tributaries from the main river.

Showboats were floating theaters presenting melodramas, comedies, musical acts, and even circuses. They were towed by steamboats from landing to landing. Showboats were very popular on the Monongahela and Kanawha rivers in West Virginia. The annual visits of the showboats were a highlight of summer for river towns. Many showboats tied up for the winter at the mouths of the Little Kanawha and Kanawha rivers, because these places were safe harbors from winter ice.

Capt. Thomas J. Reynolds was among West Virginia's famous showboat operators. He was born at Point Pleasant in 1888 and started his river career by fishing for mussels. He later acquired the moving-picture boat Illinois. In 1917, he built his first real showboat and named it America. His family, which eventually included nine children, lived on the boat when they were not wintering at Point Pleasant. In 1923, he built the Majestic, which is now moored at Cincinnati and still operates as a showboat.

The Bryant family of Point Pleasant is West Virginia's other famous showboating family. Twenty-five-year-old Samuel and his 13-year-old wife, Violet Bryant, had come to America from England in 1884. They started a one-wagon medicine show and traveled across America. They reached the Rocky Mountains before they returned to the Ohio River and their first jobs on a showboat in 1900. Capt. Edward Price of the showboat Water Queen billed them as the "Four Bryants," since a son, Billy, and daughter, Florence, were a part of the act. The Bryants built the Bryants New Showboat in 1918 and operated it until World War II.

The Pope Dock Company of Parkersburg was the builder of some of the most famous showboats. At the mouth of the Little Kanawha River the company built the New Grand Floating Palace in 1901; Eisenbarth & Henderson Floating Theatre—The New Great Modern Temple of Amusement in 1903; Sunny South in 1905; and the world's largest showboat, the Goldenrod, in 1909, as well as many others. Like the Majestic, the Goldenrod is still in operation as a showboat, at St. Charles, Missouri. These two are among the last of the hundreds of showboats that once operated on America's rivers, and they both have West Virginia roots.

Operators such as Capt. Augustus B. French and his wife, Callie Leach French, who was the first woman to obtain a pilot's license in 1888 and the second woman to be granted a captain's license, were known for the quality of their boats and their shows.