Concerted settlement in the East Side neighborhood began during the 1880s with well-to-do settlers with upper-class roots developed the East Side along Lake Michigan. The location had early appeal due to its location atop the bluffs overlooking Lake Michigan. Many of the extravagant homes are still standing today, particularly around the North Point section. Away from the lake, workers for the nearby tanneries settled in, creating an ethnically diverse area over the decades. By the early 1870s East Brady Street began to emerge as a center of Polish commerce with a concentration of working class Polish immigrants living in the surrounding neighborhood. In the 1920s the ethnic focus of the neighborhood began to shift to Italian, reaching its peak in the 1950s.
In 1960s and 1970s, the Lower East Side neighborhood became Milwaukee's counterculture and hippie epicenter. In the 1990’s, several Business Improvement Districts were formed on North Avenue and Brady Street. These business areas have welcomed a more diverse array of businesses. A variety of ethnic restaurants and local taverns dot these popular commercial streets, along with a mix of traditional and eclectic businesses, many in restored historic buildings. Prospect Avenue, which was once home to many of Milwaukee's grand mansions, saw several of the historic structures demolished and replaced with high-rise residential structures.
The East Side is considered by some as Milwaukee's melting pot, with a mix of hipsters, hippies, college students and young professionals converging in the area's diverse restaurants, bars and stores.
Oriental Theatre, a movie palace still in operation, was built in 1927. The University of Wisconsin–Milwaukee was established in 1956, replacing the smaller Downer Avenue Teachers College.
Milwaukee's East Side is home to several museums and galleries including the Villa Terrace Decorative Arts Museum, Charles Allis Art Museum, Emile H. Mathis Art Gallery at the University of Wisconsin-Milwaukee, the Green Gallery, and the Jewish Museum Milwaukee.
The East Side contains several neighborhoods including the Lower East Side, Murray Hill, Northpoint, Lake Park, Riverside Park, the Upper East Side, Cambridge Woods and Downer Woods. The neighborhoods to the north and east are traditionally more residential and affluent while those to the south and west take on a more urban and mixed-use identity.