The first established settlement of the area that eventually became known as Josephine would seem to be the small village that emerged around Raphael Semmes' Baldwin County property. In 1841, Semmes moved his family from Maryland to farmland he acquired at the head of what became Semmes Bayou, now known as Roberts Bayou. At the time, Semmes was a lieutenant stationed at the Pensacola Navy Yard assigned to survey the coast of Florida and the Gulf Coast. The family settled into a homestead that Semmes called Prospect Hill. Other Navy colleagues acquired farms nearby, establishing "a very pleasant colony of nautical farmers." Semmes' return home from the Mexican War in late 1847 was marked by a county celebration held at the small village of Prospect Hill. Raphael Semmes later achieved fame as an admiral in the Confederate navy.

The first post office in the area was established in 1881, with Amos Ross, for whom Ross Point is named, as postmaster. The settlement was then named for Ross' daughter, Josephine. The sailboat carrying mail stopped at the Ross residence, the old Moss Oaks home, during its trips between Pensacola and Mobile. This continued after the John McKee Climie family acquired the Moss Oaks home in 1890. In 1905, the McPherson family's 52-foot freighter, the Mexiwana, began picking up freight, mail, and passengers at the sawmill railhead at Millview, FL.

The Southern State Land and Lumber Company mapped Josephine in 1898 for the McPherson family, who had just bought the Semmes property. They built the Mexiwana Hotel on the site of the former Semmes home. The hotel was consumed by fire in 1935.

About 1901, Semmes Bayou became known as McPherson Bayou. The inlet acquired its current name, Roberts Bayou, after Leon McPherson's death in 1923.

A Baldwin County School was built in Josephine in 1903 at the southwest corner of what is now Wolf Field. It was a one-room school with grades 1-6. Isabell Ballard Cowham, who died in 1998 at the age of 94, remembered it well, especially two teachers - Miss Evan Kranz and Miss Mary McConnagy. At the school, the older boys supplied the big, pot-bellied stove with wood, which had to be carried outside when it once caught on fire. At Christmas, there was always a party at the school. The school closed around 1917 for lack of students and was used as a community center before it later burned.

In 1914 Mr. J. Tagsherer built a bakery oven now located on the Lawrenz family property. A number of Perdido Bay settlements received baked goods from this old world style brick oven. Later, the bakery was moved to Foley where people along the L & N Railroad in south Baldwin County enjoyed the delicious bread.

1904 Party at Mexiwana Hotel for Elsie McPherson
Moss Oaks-Climie Home on Ross Point
Store At Pirates Cove
McPherson Home
McPhersons On The Beach
S.S. Mexiwana
Josephine Post Office
Schlinkerk home on Roberts Bayou c. 1913
Southern State Land Co. Survey
Raphael Semmes
Bakery Story

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