Why Was Leonard Destin moved from East Pass during the Civil War?

H.C. "Hank" Klein History Mystery
USS Water Witch – 155-foot Union Steam Gunboat

Last month we discussed the blockade of East Pass by the Union during the Civil War. Another History Mystery of Destin is why Leonard Destin and his family were moved from East Pass and was he actually “trading with the enemy” as a letter from a member of the Walton Guards stated.

While there were many Union vessels that blockaded the East Pass, we found that the entries in the log of the USS Water Witch and the USS Wyandotte gave us what we believe is the clearest picture of what the Leonard Destin family must have faced living at East Pass at the beginning of the War Between the States.

During the months of July and August 1861, both vessels fired their guns often. Usually it was just practice. They shot at targets on the beach on Santa Rosa Island. Sometimes there were skirmishes with the Walton Guard at East Pass.

Leonard, his family, and anyone else living near East Pass must have been extremely frightened by the very presence of Union gunboats stationed at the East Pass. Also the continual gunfire of the large 32-pound cannons, 24-pound Howitzers, small arms practice by the crew must have been very loud and frightening. There was also occasional interaction of the Union Navy with the Confederate Walton Guards at East Pass. Those interactions must have made Leonard and his family feel that they were in the middle of the local conflict.

Those conflicts did not affect Leonard and his family directly. But there were direct interactions with the Destin’s that may have made them think twice about remaining at East Pass.

The day after the USS Water Witch arrived at East Pass an entry in their log show that they sent a cutter to cross the bar, on July 6, 1861. They found that they had only five feet of water and they “found a sloop at anchor and a house apparently abandoned by its inhabitants.”

On July 12, 1861, the USS Water Witch log entry states that they “sent the gig to assist in towing the sloop about a ½ mile inside East Pass and was abandoned after taking out the following articles – 1 double barreled fowling piece, 1 compass, 2 pairs of shoes, 1 time piece, 1 spring balance, 1 hat, 1 coffee mill.”

Apparently Leonard returned close enough to his home to realize that his sloop had been moved. Going aboard his sloop he found that his personal property had been taken by the Union Navy. According to the entry in the ships log on July 13, 1861, he left his sloop late in the afternoon and went to the USS Water Witch and confronted the crew and asked for his belongings back.

The log stated, “a boat came from off the sloop anchored inside and received all of the property belonging to her except a double barreled shot gun which was not returned.” If there was any “trading with the enemy,” it looks like this is as close as it got – Leonard retrieving his own belongings.

I am sure the Destin family felt like they were at the epicenter of the conflict between the Union and the Confederate troops by simply living at East Pass. As they heard the gunfire from the Union gunboats, even if it was just the crew practicing, they must have been frightened. Returning to his home and vessel and seeing that the Union troops had been there, especially when they took his belongings, must have angered him.

Having to go to the Union gunship to retrieve his belongings was probably the last straw. Especially when they would not return his double barreled shotgun – maybe it was time to move.

Leonard and his family went to Four Mile Landing, on the opposite side of the Choctawhatchee Bay, where Leonard had been married to Martha McCullom in 1851, to wait out the war. While at Four Mile Landing, Leonard and Martha Destin’s 5th child, Hattie Destin, was born on November 18, 1862. The name for the Four Mile Landing area was changed to Freeport after the Civil War.

I doubt there was any real “trading with the enemy.” Instead I believe Leonard Destin and his family “headed for the interior” about Aug. 10, 1861, for their own protection and to get away from the Union blockade and the conflicts between the Union troops and the Walton Guards that were going on at East Pass during the Civil War.

H. C. “Hank” Klein is a Destin historian who visits often and lives in North Little Rock, Arkansas with his wife (the former Muriel Marler of Destin). Klein recently published a historic book about Destin's pioneer settlers. DESTIN Pioneer Settlers...A Land History of Destin, Florida from 1819-1940 can be obtained from, Tony Mennillo of Arturo Studios at 850/585-2909, Dewey Destin's Restaurants, in Destin, the Magnolia Grill in Fort Walton Beach, or Bayou Books in Niceville. Klein can be contacted at