2026: Focus on Oakland Avenue
Shorewood’s “Main” Street is Lined with Stories
Oakland Avenue, from Capitol Drive to Glendale Avenue, will be under construction for most of 2026. The road surface is in desperate need of replacement and aging underground utilities will also be upgraded. The last major reconstruction of Oakland took place in 1996.
As you walk along the Avenue this summer, look beyond the dust, noise and lack of parking and imagine all of the changes that have taken place in its long history.
For much of the 19th century, the street, which is on a section line, wasn’t much more than a path for use by farmers and land speculators. Oakland Avenue, a street in Milwaukee, was extended north all the way to Day Avenue in Whitefish Bay near the end of the century. By 1898, the Milwaukee Electric Railway and Light Co. (TMER&L) extended street car service from Milwaukee north along Oakland Avenue. Passengers from Milwaukee rode the street car to visit the Pabst Whitefish Bay Resort, Mineral Springs Park in Shorewood and summer cottages along the lake.
When East Milwaukee (later Shorewood) incorporated in 1900, most of the early development took place on the south end of the Village – primarily bars, rooming houses, and the amusement park. But the blocks north of Capitol (then known as Mineral Spring or Atwater Road) started to fill in with the construction in 1910 of the Armory on the northwest corner of Oakland and Capitol. It was the home of the 105th Calvary Unit of the Wisconsin National Guard known as the Light Horse Squadron. Small businesses followed on the northeast side.
By 1929, the National Guard had moved to Richards Street and the large Armory property was opened for development. The Art Deco building, which included the Shorewood Bank, was completed in 1930. Businesses in that building included a Drug Store on the corner, a Ben Franklin and a Heinemann’s Restaurant. Eventually most of the space was taken over by Harley’s Store for Men. On the east side of the 4000 block there was another Drug Store and a number of small businesses including Miller Shoes and Palmer’s Delicatessen.
Help Us Tell Oakland’s Story
Do you have questions about Oakland Avenue? Or stories to share about buildings or activities on the street? Or pictures taken along the street? Please contact us at shorewoodhistory@yahoo.com.
We will try to answer your questions and use your stories on this web page and other communications throughout 2026.