Donald Trump indicted for allegedly mishandling classified documents seized at Mar-a-Lago

Sheboygan Co. Fair marks 166th year after search for a home in early years

Beth Dippel
This 1950s view of the Sheboygan County Fair shows the old midway looking north toward the cattle barn. It includes the trademark Ferris wheel, albeit a much smaller version than today. The race track is at right. Early fair events included a beautiful baby contest, gypsies who told fortunes, wheelbarrow races and greased pig contests.

Each September, the Sheboygan County Fair creates grand memories for those who attend, amazing for an event marking its 166th year. The five-day festival brings fun, farm animals and family, along with blue ribbons and great food to the citizens of the county.

An American classic, the fair became a mainstream event in the mid-1800s, though the first were held much earlier; 1641 in New Netherland, and 1807 in Pittsfield, Massachusetts. The nation’s first state fair was held in Syracuse, New York, in September 1841. There, an estimated 10,000-15,000 people heard speeches by notables and viewed animal exhibits, a plowing contest and samples of manufactured goods for the farm and home.

Today, 47 of the 50 United States, and Washington D.C., have fairs. Only Rhode Island, Michigan and Connecticut lack such an event.

County fairs developed about the same time as state fairs, spearheaded by agricultural groups looking to create community for farmers. The Waukesha County Fair is Wisconsin’s oldest. It, too, began as an agricultural fair in 1842 in the little town of Prairieville. Crowds of up to 4,000 people attended the 1853 fair where they enjoyed floral displays and a Ladies’ Equestrian Display.

September 1955 brought ostrich racing to Plymouth’s fair.

The first annual fair and cattle show of Walworth County was held in the Village of East Troy on October 16, 1850. A total of 35 first premiums, 17 second premiums and 3 third premiums were awarded.

Sheboygan County jumped into the fray in 1851 when Sheboygan County Agricultural Society held the first annual fair in Sheboygan Falls on the hill behind the Free Hall, located on Madison Street. The agricultural displays were housed on land in the Cole Historic District; the barn used at the time is now part of two houses on the corner of Adams and Michigan Streets in Falls directly behind the old Thorpe Hotel (Richards Supper Club).

In 1852, the fair was held at Plymouth, and in 1853 Sheboygan hosted the event.  Beginning in 1854, Sheboygan Falls was again home to the event. The 1857 fair was considered the first permanent location as the grounds were improved and buildings were constructed. This location was a plot on the west side of town, a part of the property of Benjamin E. Sanford, a prominent Sheboygan Falls manufacturer and horseracing aficionado.

Sanford’s land was located on the south side of the road near the old Point Drive In. A native of England, Sanford came to Sheboygan Falls to join the Phoenix Iron Works. In the May 14, 1870 issue of the Evergreen Times, the following item appeared: "B.E. Sanford is clearing the ground preparatory to making a track for horse racing on the flat west of his house. When it is finished, we expect his splendid span of blacks will be ready to challenge the county and perhaps the state."

The first annual fair and cattle show of Walworth County was held in the Village of East Troy on October 16, 1850. A total of 35 first premiums, 17 second premiums and 3 third premiums were awarded.

Plymouth’s Race Track was a big feature. A half mile race track was completed in July 1897, and to mark the occasion, a harness race was scheduled. First prize in the horse race was $25. Motorcycle racing was added in 1909 and car racing came later. This image shows the Plymouth grandstand in about 1900.

Sheboygan County jumped into the fray in 1851 when Sheboygan County Agricultural Society held the first annual fair in Sheboygan Falls on the hill behind the Free Hall, located on Madison Street. The agricultural displays were housed on land in the Cole Historic District; the barn used at the time is now part of two houses on the corner of Adams and Michigan Streets in Falls directly behind the old Thorpe Hotel (Richards Supper Club).

In 1852, the fair was held at Plymouth, and in 1853 Sheboygan hosted the event.  Beginning in 1854, Sheboygan Falls was again home to the event. The 1857 fair was considered the first permanent location as the grounds were improved and buildings were constructed. This location was a plot on the west side of town, a part of the property of Benjamin E. Sanford, a prominent Sheboygan Falls manufacturer and horseracing aficionado.

Sanford’s land was located on the south side of the road near the old Point Drive In. A native of England, Sanford came to Sheboygan Falls to join the Phoenix Iron Works. In the May 14, 1870 issue of the Evergreen Times, the following item appeared: "B.E. Sanford is clearing the ground preparatory to making a track for horse racing on the flat west of his house. When it is finished, we expect his splendid span of blacks will be ready to challenge the county and perhaps the state."

Not to be outdone, Sheboygan held its first Annual Sheboygan Driving Park and Exposition in 1888 at Driving Park on the north west side of town. This marked the beginning of a competition between Falls and Sheboygan, which included duplicate fairs through 1890. From 1891 until 1895, the fair was back in Sheboygan. However, dissension between the Sheboygan Driving Park and the County Agricultural Society resulted in no fair being held in 1896.

An advertisement from the 1926 Sheboygan County Fair; five great days in August.

Fortunately, in 1896, Plymouth residents took charge and the Sheboygan County Agricultural Association was organized, ending the situational soap opera.

In 1897, the fair began its permanent run in Plymouth at a new 23-acre site on the east side of the city. The centralized location on Fairview Drive was a boon to the success of the event, as merchants from all over the county traveled to set up displays and hawk their goods. Farm exhibitors showed keen interest by entering more animals and bigger vegetables each year. Plymouth seemed to be the perfect and logical location.

A half-mile race track was completed in July 1897, and to mark the occasion, a harness race was scheduled, beginning a deep racing tradition in Plymouth. There were also bicycle races and foot races that day. First prize for the horse race was $25, but the foot race winner received only an umbrella, generating complaints from the sprinters.

In 1900, Plymouth virtually shut down to give everyone a chance to attend. Motorcycle racing moved in to compete with the horses in 1909, and spectators began to attend the fair in horseless carriages. In 1910, a special gate was opened just for automobiles to prevent spooking of the horses. 

A special parade of autos was held one year with the top prize of $11 to be distributed between the top five cars. Only four winners claimed a prize. The fifth became bogged down in the mud somewhere in the country.

A model of a country home lighted by electricity was the big attraction in 1912, and in 1914 homemakers learned how electricity could keep butter and cheese fresher. An airship visited the fair in 1919 along with an exhibit on torpedoes.

Advertisements from 1914 boasted, “The Six Moroccos, also known as the Wild Moors, Whirlwinds of the Desert, are here to introduce a new show, startling and daring, with Oriental juggling, dancing and soudanic drills.” Soudanic referred to performers from Timbuctoo. It goes on to discuss the Riding Davenports, who were "peerless and scintilant, performing the most daring feats of bareback riding ever.” Love the descriptors!

The 1933 WHBL booth at the Sheboygan County Fair, where programming was done live, direct from the County Fair. Three Lovely Ladies of Harmony and German Hour entertained fairgoers. The rear of the old grandstand is at right and the Sheboygan Press booth is at left. Softball games from Roosevelt Park were also aired live during the fair via WHBL.

The 1910s through the 1930s were considered the glory days of the fair. Heated political speeches, Wild West shows, horseless carriage parades and fortune telling gypsies enlivened the event. Airplane stunt shows became a big thing during the late 1920s as did harness races of trotters and pacers.

Stunt fliers entertained crowds at the 1927 fair, the final day of which was marred by the burning of a large cross, evidently by local Ku Klux Klan members.

The 1937 fair had WHBL broadcasting live from the Midway. Featured performers and exhibitors were interviewed. Musicians performed; the German Beer Garden of the Air, sponsored by Jung’s, was a highlight. Leonard Kranendonk, famed local baritone and accordion player entertained with a selection of his favorite opera pieces.

Stock car racing replaced harness races in the late 1940s.

Today, we see everything from farm machinery to sewing projects, midway rides to ice cream cones, champion pigs to carnival rides. There is something new and different each year.

The five-day extravaganza is a grand celebration of life in Sheboygan County, happily anticipated by everyone, and we’re lucky to have one of the finest in the state. Don’t miss it, Aug. 31 through Sept. 4.

Dippel is executive director of the Sheboygan County Historical Research Center.