Prehistory - The Windover people lived in this area.
1600s - Spanish missionaries seek to convert the Jororo tribe.
1701 - Joachin de Florencia leads an expedition from St. Augustine to quell a Jororo uprising. He dubbed this area "La Rinconada."
1728 - The Jororo tribe was reportedly decimated by slave raids and disease, opening the Central Florida frontier for settlement by a new tribe: the Seminoles.
1763 - Florida becomes a British colony.
1783 - Spain regains control over Florida.
1821 - Florida becomes a U.S. territory.
1824 - Mosquito County was created.
1838 - Fort Gatlin established during Second Seminole War.
1842 - Congress passes the Armed Occupation Act.
1843 - Benjamin Whitner surveys this area, naming Lake Conway.
1845 - Florida becomes a state, and Mosquito County changes its name to Orange County.
1850 - Wright Patrick named the first postmaster in this area.
1852 - Aaron Jernigan raises a company of volunteers to quell a Seminole uprising.
1856 - Third Seminole War erupted, Orange County residents voted to move courthouse to vicinity of Fort Gatlin.
1859 - William Wright is murdered at the post office in Orlando, causing many members of the pioneer Jernigan family to flee justice by moving to Texas.
1861 - Florida secedes from the Union despite dissenting votes from local delegates William Woodruff and Isaac Rutland.
1865 - Local pioneers Burb and Cornelius Johns witness Lee's surrender to Grant at Appomattox, Virginia, marking the end of the War Between the States.
1870 - A bloody feud erupts between the pioneer Barber and Mizell families.
1873 - Nationally known writer Will Wallace Harney built a fanciful "Pine Castle" on the shores of Lake Conway.
1876 - Presbyterians built the first actual church in this area, near the shores of Lake Jessamine. They later moved to bigger facilities downtown, what is now First Presbyterian Church of Orlando.
1877 - The Reconstruction Era ended.
1879 - The Pinecastle Post Office was established with Clement Tyner the first postmaster.
1881 - The South Florida Railroad tracks reached Pine Castle.
1882 - Will Harney donated the land for a public school in Pine Castle, still occupied by Pine Castle Elementary School.
1887 - Rev. Thomas Jefferson Bell organized the First Baptist Church of Pine Castle.
1891 - Will Harney's old Pine Castle estate was subdivided for development.
1894 - Clement Tyner recorded a plat of the Town of Pine Castle.
1895 - The Great Freeze destroyed area citrus crops, causing many pioneers to abandon their groves.
1898 - War with Spain spurred economic recovery.
1900 - Pine Castle's venerable Union Church was built as an interdenominational place of worship.
1909 - Pioneer settler Paul Macy built what became known as "The Crawford House."
1911 - The Pioneer Association of Orange County was established.
1912 - Will Wallace Harney, builder of the original Pine Castle, died in Jacksonville.
1915 - The Town of Pine Castle was incorporated, with Charles Jefferson Sweet elected its first mayor.
1917 - Pine Castle mobilized for the First World War.
1923 - Pine Castle hosted a state convention of florists at Pleasure Beach.
1924 - The cities of Belle Isle and Edgewood were formed by Pine Castle residents who objected to the town council's plans to issue bonds for capital improvement projects.
1925 - Pine Castle received a new state charter reflecting its reduced boundaries.
1928 - The Great Depression started a year early in Pine Castle with the collapse of the real estate market and a Mediterranean fruit fly infestation.
1930 - The venerable Union Church was sold by its trustees to local Methodists for their sole use.
1932 - The Town of Pine Castle went bust as a result of the Great Depression, surrendering its tax rolls and other records to Orange County officials.
1934 - The inimitable Granny Harris, matriarch of a large extended pioneer family, died at the advanced age of 97.
1938 - Local resident Bob Etty was the prime suspect in the sensational murder of Dolores Myerly at Orlando's landmark San Juan Hotel.
1940 - Orlando Air Base #1 opened near Pine Castle, forerunner of the modern Orlando International Airport.
1941 - Pine Castle mobilized for the Second World War.
1942 - Area residents marked the centennnial of the Armed Occupation Act with "Founders Week." Festivities included a parade in downtown Orlando, with the largest contingent coming from Pine Castle.
1945 - The Pine Castle Boat & Construction Company completed their "miracle order," doing their part to win the war.
1950 - The local post office change its name to "Pine Castle," two words instead of the original "Pinecastle."
1952 - Durrance Elementary School in Pine Castle was the first campus in Orange County to integrate.
1957 - St. Mary of the Angels Episcopal Church was established on Matchett Road.
1958 - Pine Castle Air Force Base was renamed McCoy Air Force Base to honor the late Colonel Michael McCoy.
1959 - Pine Castle's venerable Union Church was moved to the Narcoossee area to serve as the new home of Lake Whippoorwill Baptist Church.
1963 - The Walt Disney Company announced plans to build a huge new entertainment complex in Orange County.
1964 - American Legion Post #286 was established in Pine Castle.
1965 - The Southern Garden Arts Center was organized in Pine Castle.
1967 - Pine Castle United Methodist Church dedicated its new brick sanctuary.
1971 - Walt Disney's Magic Kingdom opened.
1973 - Pine Castle Pioneer Day was held at the old Center for the Arts. It was only a one-day event, but grew to become a weekend festival.
1977 - Pine Castle's modern post office building opened on South Orange Avenue.
1980 - The venerable Crawford House was moved from its original location on Fairlane Avenue to a new site on Randolph Avenue.
1983 - Pine Castle Christian Academy was organized.
1989 - Edgewood successfully blocked construction of a "Central Connector," that would have bissected the community.
1990 - An historic log cabin from Kentucky was reconstructed on the campus of Pine Castle Christian Academy.
2001 - The Pine Castle Urban Preservation District was created by Orange County voters.
2004 - Hurricanes Charley, Frances, and Jean struck this area, damaging many buildings and trees.
2010 - Pine Castle Pioneer Days, Inc., was established as an independent public charity to ensure longevity of the community's hallmark festival.
2014 - Pine Castle Pioneer Days switched venues to Cypress Grove Park with the assistance of Commissioner Pete Clarke and Orange County government.
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