Historic Highway 41’s Memorable Stretch of Commerce

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Historic Highway 41 was constructed in 1926 as the major North-South highway between Chicago and Milwaukee. This was the original route between the two cities until Interstate 94 was constructed in the mid ‘60s. Worth noting is U.S. Highway 41 runs from Miami, Florida to the Upper Peninsula of Michigan. It winds its way through the Everglades of Florida, into Georgia, Tennessee, Kentucky, Indiana, Illinois, and Wisconsin.

Highway 41 enters Wisconsin and runs north and south along the eastern edge of the state, from Pleasant Prairie in the south to Marinette in the north. The South 27th Street section of Highway 41 in Milwaukee, specifically the area between Oklahoma and College avenues, features over 400 businesses within a four-mile stretch.

South 27th Street is one of Southeastern Wisconsin’s most vibrant and lively streets, home to a wide variety of different businesses: restaurants, hotels, motels, banks, auto dealerships, retailers, movie theatres and family-owned businesses. We all know how the area looks today, but what did it look like before? Here is a list of by-gone businesses that used to call Highway 41 home:

Southgate Shopping Center

Later called Southgate Mall, the Center was the first significant post-World War II suburban-style shopping center in the Milwaukee area. In 1949, local brewery supplier Kurtis Froedtert began the framework for Southgate and three other major suburban-style shopping centers in the area during a period of retail development nationwide. Milwaukeeans found Southgate irresistible.

The center opened on Sept. 20, 1951. The developers were pleasantly surprised when more than 60,000 people showed up for their “family party.” The entertainment was vintage Milwaukee: Polish and Italian folk dancers, polka bands on the blacktop, a visit from Alice in Dairyland, a world champion flagpole sitter and fireworks. The addition of a Gimbels department store in 1954 gave Southgate a genuine anchor. Krambo grocery store, Milwaukee’s largest grocer, opened on the South end in the next year. Southgate became a regional magnet for many years. In the summer of 1999 most of the mall was demolished.

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Pinky’s Bowling Alley

Originally known as Eugene Lanes, the establishment would become better known as Pinky’s Bowl. Bob Pinkalla was the second-generation owner of the alley. Pinkalla was a part of the disappearing generation of bowling center owners who were bowlers first who transformed their passion for the sport into successful businesses.

According to Doug Schmidt’s book They Came to Bowl, in 1939 Eugene Pinkalla converted his tavern at the corner of 27th and Oklahoma on Milwaukee’s South Side into a six-lane bowling alley. His two sons, Bob and Wayne, were raised there. On April 20, 1960, Bob and Wayne became the first brothers to bowl 300 games in the same league game at Pinky’s. The two were in a three-team league and finished with an 859 game, which is the third best nationally. Bob would grow up to become a local, state, national and international champion on the lanes while remaining involved in the family business.

In 1962, the venue doubled in size to 16 lanes, and would remain open until 1989. Today, the former footprint of Pinky’s is a parking lot for the emergency department at St. Luke’s Hospital.

Wildenberg’s Evergreen Hotel

Although now standing in vacant silence, this building was the mansion built in the 1850s by Jacob Nunnemacher, who ran the large Nunnemacher Distillery on this property. An ambitious descendent, Robert Nunnemacher, was responsible for perfecting the pneumatic drum malting process in 1880 that revolutionized brewing in America. He established Milwaukee's first malt house, the Krause-Merkel Malting Co. (which became the National Warehouse in 1925) and subsequently started the Galland-Henning Pneumatic Malting Drum Manufacturing Co. in 1887.

Edward Wildenberg bought the property in the 1940s as a tourist campground with 10 cabins surrounding the house. Eventually the cabins were removed and trailer homes were put in their place during the 1950s and ‘60s as it was a more “lucrative” venture. The Wildenberg’s Evergreen Hotel, Bar and Mobile Home Park served as both an inexpensive long-term sanctuary for residents and a weekly rooming house. The bar was said to have been the center of social activity for residents and locals alike. It became a regular stop for Chicago gangsters on their way up North. The future for the building and property remains unclear. Over the years there’s been talk about redevelopment, but there hasn’t been a solid plan to move forward. It’s definitely a Milwaukee landmark and deeply rooted in the city’s history.

Palomar Rink

Located at 3314 S. 27th Street, across from Southgate, Palomar opened in 1939 on the eve of World War II and survived through the war and postwar years through the 1950s. The rink was a favorite destination on Saturdays and the Sundays. The bus/streetcar line ended on Oklahoma Avenue, requiring a several blocks long walk to the rink. At the time Oklahoma Avenue was at the end of the city and the beginning of undeveloped farmland.

The rink’s organ music entertained an average of 700 to 900 skaters a day during its height. The building was demolished in 1966-67 to widen an intersection. The roof arches were salvaged and reused as the roof of Rollero Skate Center in Cudahy.

41-Twin Drive-In

Located on South 27th and Drexel Avenue in Franklin, the drive-in opened in July 1948 with a capacity for 1,000 cars. In 1949, it was twinned and became the 41 Twin Outdoor Theater. Over the years it expanded screens and car capacity. Drive-Ins were a high point for Baby Boomers. Where else could you see three movies and sneak your friends in the trunk of a car. It’s closing in 2001 was not due to a decline in business. Rather, the land became so valuable the owners decided to sell. Demolition began in April 2002. The concession stand caught fire during demolition which added insult to injury. A small memorial plaque off South 27th and Drexel can be seen today on Northwestern Mutual’s property.

Perhaps the next time you find yourself on historic Highway 41, you will have fond memories of some of these by-gone locations.