The area around East Dubuque has seen its share of action over time. Native Americans of the Hopewell period (200 BCE–500 CE) built numerous mounds on the hills (many of which are preserved in Gramercy Park). The first European to settle in the area was Eleazor Frentress, who arrived in 1827. (The cabin built by the Frentress family is now on display at the Mississippi River Museum in Dubuque.) Thomas Jordan showed up five years later and got a license to operate a ferry across the Mississippi River; the settlement was therefore known as Jordan’s Ferry for a while.
The town was platted in 1853 as Dunleith; the name was apparently chosen in honor of a Scottish city that had been home to several of the founders, although there does not appear to be a town of Dunleith in Scotland today. Dunleith got a big boost in 1855 with the arrival of the Illinois Central Railroad; it triggered an economic boom that lasted for the next decade. When Dunleith incorporated in 1856, its industry included breweries, a nail factory, farm machinery, and a barbed-wire manufacturer.
In March 1866, 100 East Dubuque Catholics walked across the frozen Mississippi River to attend mass (their Priest was ill). On the way home, the ice broke free and they were carried down river; four bone-chilling hours later, the ice rammed into a sandbar, allowing all of them to escape unharmed.
Dunleith had developed something of an unsavory reputation, so the town decided a name change was just the fix it needed: in 1879, Dunleith became East Dubuque. Old habits die hard, however, and the town maintained a reputation for being a rough place. A riot erupted on June 30, 1919, the day before Prohibition took effect, as anxious drinkers took out their frustrations on civic landmarks; city hall and the fire station were damaged and prisoners were freed from jail. During Prohibition, stills operated in the hills and river islands, and Al Capone was reputed to be involved in the local liquor business. East Dubuque was known as Sin City because of its speakeasies, roadhouses, and gambling halls. When Prohibition ended in 1933, Illinois enacted liquor by the drink and Iowa did not, so East Dubuque’s Sinsinawa Avenue was again a busy place for those who preferred a little kick in their beverage.
Local doctor U.S. Lewis got his 15 minutes of fame in 1949 when he was featured in a Ripley’s Believe it or Not cartoon for delivering three babies in three states (Illinois, Wisconsin, Iowa) within 24 hours (7 hours, actually). The local economy received a boost in 1964 with the construction of a fertilizer plant (still around) and again in 1967 with the arrival of go-go girls (long gone).