PANHANDLE PIONEERS REUNION NOV. 1: Crain Family Settled Area in Early 1800s

Posted on October 21, 2025 by Romi White

Long-time locals with deep roots will gather on November 1 at Holley Assembly’s dome to celebrate their rich heritage. The potluck luncheon will start at 11 a.m. Those whose families settled the area in the 1800s are cordially invited to attend.

Descendents of William Lewis Crain will be attending the reunion. Crain fought with Gen. Andrew Jackson during the First Seminole War and later settled his family on what is now Eglin Air Force Base property. Lewis was buried on a bluff above Crain Branch in what was his favorite turkey hunting spot and today is part of Faulk Cemetery (his daughter married a Faulk). His family was known to live at Wolf Creek and Whitmire Island before moving up to Milton.

 

Willie Lewis Crain’s tombstone states he fought in the U.S. Army Indian Wars 

Willie’s son, Lewis, according to his obituary, was born on Yellow River in 1830 and later enlisted in the Conferderate army in Company E 15th Florida calvary, serving throughout the Civil War. He was wounded several times.

Lewis, on Santa Rosa’s first census in 1850, listed his profession as a lawyer. He was also an early Mayor of Milton, who “made a splendid record in that office for truth and justice,” per a news article publishing in 1917 upon his passing. 

Lewis donated the land for Crain Cemetery, which is located on the back gate road to NAS Whiting Field. 

A photo of Crain Church, which was located at Crain Cemetery, before it was burned down. Bottom row, left to right: Mary Ella Williams Mitchell, Vashti Carpenter Henderson, and Madrienne Williams Rino. Top row, left to right: Opal Williamson Johnson and Ella Walls Carpenter.

Lewis’ son, Samuel Tildon Crain, was born August 30, 1876, in Milton. His mother was Mary Diadema “Damie” Pyburn, who was born February 22, 1840 in Santa Rosa County.

Sam and his wife, Annie Belle McCary, were the parents of George, Nellie, Mae, Bo, Ray, Margaret, Sam. He died on October 18, 1956 at the age of 80. He was a butcher and their family lived on Ann Street, which is now located on the campus of First Baptist Church in Milton.  Their sons were talented musicians who played by ear and performed as backup musicians on the Grand Ole Opry – back when it was at the Ryman Auditorium.

Samuel Tildon Crain

The Crain family lineage dates back 13 generations and future stories will include details about its service in WWII, Civil War, U.S. Army Indian Wars and the Revolutionary War.