Portsmouth Ohio's roots began in the 1790's when the small town of Alexandria was founded just west of where Portsmouth is today. Alexandria was flooded numerous times by the Ohio River and the Scioto River. In 1803, Henry Massie spotted a place to move the town away from the flood plains. He began to plot the new city by distributing the land and mapping the streets. Portsmouth was founded in 1803 and was established as a city in 1815. Alexandria soon disappeared. Portsmouth quickly grew around an industrial base with the completion of the Ohio and Erie Canal, and the construction of the N&W railyards and the B&O junction. This greatly benefited Boneyfiddle (which is a west-end neighborhood in Portsmouth), where grand buildings were constructed with the wealth from the commerce. As time passed, much of the commerce began to move towards Chillicothe Street, which is still today the main thoroughfare of Portsmouth. While Boneyfiddle is receiving new life, it is a shadow of its former self. Another notable part of Portsmouth's history in the 19th century was its importance on the Underground Railroad. It was located on a route that continued north to Detroit and into Canada.
Even though the city was on higher ground, it was still prone to flooding. The city had great deal of flooding in 1884, 1913, and 1937. After the flood of 1937, the U.S. Army Corps of Engineers constructed a floodwall protecting the city, which prevented two major floods in 1964 and 1997. In 1992, the city of Portsmouth began honoring some of the many accomplishments of its area natives by placing a star on the riverside of the floodwall, known as the Portsmouth Wall of Fame and instituted by then mayor Frank Gerlach. Some of the honorees include Roy Rogers (King of the Cowboys), Don Gullett, and Al Oliver.
In 1992 a nonprofit group headed by Dr. Louis R. Chaboudy was formed to investigate a mural based tourist attraction on the floodwall. In the spring of 1993, mural artist Robert Dafford was commissioned and began painting murals of Portsmouth's history. He hired local art student Herb Roe as an assistant. Roe subsequently apprenticed to and worked for Dafford for 15 years. The project eventually spanned sixty 20 feet (6.1 m) tall consecutive Portsmouth murals, stretching for over 2,000 feet (610 m). Subjects covered by the murals span the history of the area from the ancient mound building Adena and Hopewell cultures to modern sporting events and notable natives.