"Oak Orchard: Located on the bay between Little Suamico and Pensaukee on county highway S, three miles south of community of Pensaukee and sometimes referred to as Southern Pensaukee in early history.  The first settlers were John Windross and his wife Jemina Skelton who arrived in circa 1847. 

The trail through Oak Orchard was known as the Green Bay Trail and later Green Bay Road and now County S.

Oak Orchard grew to have a school and the Oak Orchard Presbyterian Church, as referred to in newspaper articles, both located on the intersection County S and Oak Orchard Road. The school was located on the east side of S and the church on the west side, both on the south side of Oak Orchard Road. The school burned down in the mid 1960’s. When the school was destroyed the children from the area were bussed to Brookside, as the unification of schools was already in progress. The church burned down in the 1940’s and the school in the mid 1960’s.  When the school was destroyed the children from the area were bussed to Brookside, as the unification of schools was already in progress.

The 1880 census shows: Emaline Windross age 24, resident of Oak Orchard, teaching school and her three younger sibling, George, age 16; William age 14; and Mary C., age 7 attending school in Oak Orchard."

Oak Orchard was settled along a natural bay harbor in Lake Michigan starting almost immediately after the Windross family came in 1847. This were 4 years before Oconto County was formed from Brown County, Wisconsin, in 1851. On the 1850 census there were only two children among the 14 residents of Oak Orchard.

In the following 10 years, families settled the land around the Windross homestead and stopping off place. Each family had a number of young children brought with them from mostly New York, Vermont and Maine. Local Oak Orchard oral history has the first school classes taking place in the Windross homestead and the first school building already established well before 1860. 

Both men and women were often literate and valued education. The occupations listed for the men included ship's carpenters, fishermen/farmers, coopers, and stone cutter. Women of different ages  listed "Teacher" as almost the only occupation, other than servant" outside the home. By 1860 Mahala Sutton, age 49 and wife of farmer C.H. Sutton, was listed on the town of Pensaukee census, in the Oak Orchard area near the Windross family, as "Teaching Dist School." On the same census page, only 6 residents away was 19 year old Susan M. Knowles, also "Teaching Dist School." Susan was the daughter, and living with her farming parents William and Hannah Knowles. In this ealry time, teachers lived near their school houses, either in their own family home or with a nearby family as part of their contract.

Oconto County Reporter
August 30, 1895

Oconto County Reporter, Oconto, Wisconsin, 
October 23, 1903

Oconto County Reporter
January 8, 1904

Miss Ann Ingram returned to her school at Oak Orchard Sunday, after the usual vacation. 

In 1947 the school at Oak Orchard District 3 in the Town of Pensaukee burned. The children were transported to the grade school in Little Suamico for the remainder of the school term. The next summer District 3 and District 2 were consolidated and is known as Joint District Number 3 of Pensaukee. The children are transported by bus. Clair Matravers being the bus driver. This is the 23rd in a series of articles sponsored by the Oconto County Teacher's Association to promote better public relations in the schools of our county. Brookside and Pensaukee Schools Article