Brats, cheese, the Kettle Moraine and golf are all celebrated items that make Sheboygan County a popular destination today.

What you may not know, is that the county was once a hotspot for something less mainstream and less respectable—the sporting house business.

Prostitution came with the earliest settlers. It was well-known among commercial sailors of the Great Lakes that Sheboygan was a town where you need not spend the night alone.

Most brothels looked like ordinary houses, modest in appearance, flying quietly under the radar of the neighbors. Others were just rooms in taverns and hotels used for prostitution activities. Many were located just outside the city limits, away from the city police.

Big Apple

The Big Apple was located south of the city on Highway 141.

For years, Sheboygan County had a reputation in the Midwest for the sheer number and quality of its brothels. Estimates had them numbering upwards of 40. Why so popular here? The business was tolerated.

Among them were the Ace of Clubs at 27th and Superior, Sheboygan; The Airport Inn, one-half mile west of Sheboygan on Union Avenue; the Big Apple located south of the city on old Hwy 141; and the Brown House, 420 Pennsylvania Avenue near Harbor Lights tavern, Sheboygan.

The Nightingale, a popular nightspot, opened on May 5, 1925. Located on the southwest corner of Fortieth Street and Superior Avenue, the dance hall had a reputation for wild parties and pretty girls with busy side rooms. Locally, it was known by the less-than-delicate nickname of Gonorrhea Racetrack. Later, renamed the Dreamland Ballroom, it burned to the ground on January 7, 1956.

Nightingale Inn

The Nightingale was a popular nightspot known for its reputation of wild parties in Sheboygan County. It burned down on Jan. 7, 1956.

The most notorious establishment in the city of Sheboygan was that of Hattie Cook. Her Greenhouse was located at 13th Street and Wisconsin Avenue across the river from Garton Toy Company. Never the shrinking violet, Hattie was a prominent figure in Sheboygan life from the 1920s to the early 1950s.

Plymouth had four of its own establishments: the Bungalow and the Tin Roof located on Short Street, Six Acres on County Road PP at County Rd O, and Club Royale on old Highway 23 at what is today Pleasant View Road.

After years of dancing around the subject of illegal activity, things changed. Three events raised the ire of citizens: 1) A Minneapolis newspaper ran a series of articles about Sheboygan County’s booming prostitution business; 2) Unwanted publicity arose during the 1948 governor’s race when Candidate Walter J. Kohler Jr. brought up the issue of prostitution in Hurley, a town in his opponent’s home county. His rival, Carl Thompson, humorously retorted, “Perhaps, you should clean up your own backyard first;” and 3) The busloads of University of Wisconsin students that frequented Plymouth looking for a good time was more than a mother could stand!

On the night of January 26, 1951, 24 agents of the state beverage tax division raided six brothels: the Casino, the Greenhouse, the Farm, Club Royale, the Tin Roof and the Green Bungalow. Doors were shuttered, but more importantly, Buchen and Heffernan worked with tax authorities to go after the keepers and owners to pay delinquent state beverage taxes.

Hattie Cook house

Hattie Cook's Greenhouse was located across the river from Garton Toy Company.

Hattie Cook paid $100,000 plus interest in unpaid liquor taxes and left town. That amount of money in 1951 is nearly one million dollars today. The Casino was assessed $20,617.00 for the period of 1937-1950. Ann Joiner, madam of the Club Royale, was fined $5,337.50, nearly $53,000.00 today. The others slowly closed their doors.

It was the end of an era. The days of brothels operating openly across the county was done. The tax man won again.

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