An original Confederate Thomas Griswold & Company Cavalry Officer's Sabre w/scabbard  (Courtesy Heritage Auctions, Dallas, Texas)

The Cars did not come yesterday,” Confederate Captain Winston J.T. Stephens regretfully wrote to his wife, “Tivie,” from his cavalry picket post in Nassau County, Florida on January 28, 1864. “If you had seen the long faces as we returned to camp after waiting until nearley sun down you could then appreciate our anxieties on mail days, the only days in the week that we can hear from our dear families and then to have a disappointment is too bad.”  

At various points, service on the tracks of both the Florida Railroad Company and the Florida, Atlantic and Gulf Central Railroad had been interrupted by federal raiding parties. Hampered by the Union Army’s destruction, Captain Stephens would resort to any means necessary to keep the lines of communication open with his loved ones left behind on the home front. 

The son of Thomas P.G. Stephens, a prominent physician, and his wife, Mary Ann J. (Taylor), Winston John Thomas Stephens (Figure 1) was born July 17, 1828 in Oglethorpe County, Georgia. Following his father’s accidental death in 1836 and his mother’s subsequent remarriage to Lewis C. Gaines, Stephens and his relatives relocated to Welaka, Florida in 1856 during the turbulent period of the Third Seminole War. 

Figure 1. An original quarter plate ambrotype of Winston John Thomas Stephens produced circa 1856 while he was serving as a cavalry officer in the Florida State Militia during the Third Seminole War. (Courtesy the Stephens-Bryant Family Papers, University of Florida)

Dispelling any doubts as to Winston’s intentions at this time, Miss Carrie Latham of Welaka announced on December 18 of that year, “Mr. Stephens was going to Tampa to fight the Indians.” Accordingly, Stephens was elected second lieutenant in Captain William G. Moseley’s independent company of Mounted Florida Volunteers at Palatka on December 29. Promoted to the rank of captain six months later, Stephens was officially credited with capturing 19 American Indians on one expedition into the Everglades.

On January 28, 1858, Stephens was honorably mustered out of service at Fort Brooke, Florida. After returning to his livelihood as a gentleman planter at his sprawling 320-acre estate, “Rose Cottage,” in Welaka, Stephens wed his longtime sweetheart, Octavia Louisa Bryant (Figure 2), on November 1, 1859. 

Figure 2. An original ninth plate daguerreotype of Octavia Louisa Bryant produced circa 1858 when “Tivie” was 17. (Courtesy the Stephens-Bryant Family Papers, University of Florida)

Their marriage would ultimately produce three children; two girls (Rosalie B. and Isabella G.) and a boy (Winston).

For several decades spanning the course of the mid-19th century, Americans verbally clashed over political issues, such as the institution of slavery and the legitimacy of states' rights. The surging turmoil surrounding the ethical tenets of this sectional crisis effectually led to the decision by the legislators of Florida to preemptively secede from the Union on January 10, 1861.

Set in motion by the Fort Sumter offensive in Charleston, South Carolina, the following April, the tumult of war was unleashed between the Southern and Northern states and the ensuing whirlwind tore the country asunder. 

From the very outset of this factional conflict, Stephens, an Episcopalian and old-line Whig, had publicly admonished moderation before voicing his advocacy of the new government representing the Confederacy. Stephens enlisted in Captain Benjamin Hopkins’ Florida State Militia cavalry company, the St. Johns Rangers (Figure 3), upon its organization in September 1861. 

Figure 3. Confederate Captain Winston J. T. Stephens’ personal St. Johns Rangers cavalry guidon. (Courtesy the Winston J. T. Stephens Collection, Museum of Florida History.) 

Because of his prior Seminole War service and good reputation locally, Stephens was directly commissioned first lieutenant of that unit on October 19. The second lieutenancy position was filled by the inclusion of Henry A. Gray, a 34-year-old Palatka boat operator and entrepreneur. This cadre of officers was further augmented by the selection of Peter Peterman, a Palatka merchant, as third lieutenant. 

Booted and spurred, with a big iron strapped to his hip, Stephens rode off to battle atop his golden palomino mare, Pet. Formally mustered into the Confederate army on November 15, 1861, Stephens and the St. Johns Rangers were provisionally attached to the Fourth Florida Infantry Regiment and thereafter garrisoned at Fernandina on Amelia Island north of Jacksonville in northeast Florida (Figure 4).

Figure 4. United States Coast Survey Office 1864 map of northern Florida and southern Georgia. (Courtesy the Library of Congress)

Both well-educated, Stephens and his wife exchanged a voluminous correspondence while he actively campaigned in the northeast Florida region. Fortunately, owing to the care and consideration of their descendants, the vast majority of those letters and accompanying envelopes have survived the ravages of time. 

One such cover from this particular period (Figure 5) was addressed by Octavia to “Lieut. Winston Stephens” in “Care of Capt. Hopkins, St. Johns Rangers.” Fashioned from her original folded letter, this cover bears the double ring circular date postmark of “WELAKA/FLA.” with manuscript “Jan 24” (1862) and matching handstamped “PAID 5.” There also is a manuscript “Pd” at upper right. 

Figure 5. A stampless Confederate cover from Octavia L. (Bryant) Stephens to Winston J. T. Stephens at Fernandina, Florida. (Courtesy the Stephens-Bryant Family Papers, University of Florida)

Following Hopkins’ sudden death from fever on February 21, 1862, Stephens succeeded him as captain of the troop. 

During the month of February, Confederate General Albert Sidney Johnston and his compatriots from the Army of Central Kentucky sustained calamitous reversals in Middle Tennessee when forts Henry and Donelson fell to federal forces. Facing a severe lack of soldiers resulting from the capture of those vital military installations, commander General Robert E. Lee dispatched much-needed reinforcements from Florida to Tennessee. 

Consequently, the order to evacuate Amelia Island was issued on February 25. Subsequent to the extraction of all Southern service personnel from Fernandina and the arrival of Union troops to the surrounding area, Stephens began operating independently with his small contingent of cavalrymen. 

Stephens sent a letter to Octavia on March 13, 1862 from his bivouac near the town of Enterprise in Volusia County (Figure 6). 

Figure 6. A hand-carried stampless Confederate cover from Winston J. T. Stephens to Octavia L. (Bryant) Stephens at Welaka, Florida. (Courtesy the Stephens-Bryant Family Papers, University of Florida)

“Again I have the opportunity of writing you by Lieut Gray, as he goes to Palatka to make some arrangements for the safety of his family,” Stephens reported.

Devoid of any postal markings, the cover that enclosed this letter exhibits Stephens’ distinctive script in dark brown ink. Stephens penned his home address, along with the notation, “Attention of Lieut Gray,” referencing the hand-delivery by his second-in-command.

More than likely, Moses Smith personally carried the letter to Rose Cottage upon receipt from Gray. A local retailer, Smith regularly conveyed the mail back and forth between Welaka and Palatka in the first phase of the struggle. Smith later joined the army and finished out the war as second lieutenant of the St. Johns Rangers. 

Riverboat Captain Jacob Brock initially had been the contractor for Confederate Post Route 6524 from Welaka to Palatka, but was arrested by United States Navy crewmen on March 3 after his 298-ton side-wheel steamer Darlington ran aground in Cumberland Sound. Aptly regarded as a dangerous secessionist by his captors, Brock would languish in a Northern prison for the balance of the conflict. 

 Stephens was making preparations to fend off an expected federal amphibious assault at St. Johns Bluff, 18 miles downstream from the Jacksonville commercial district when he received Octavia’s letter written September 21, 1862 (Figure 7). 

Figure 7. A Confederate cover from Octavia L. (Bryant) Stephens to Winston J. T. Stephens at Jacksonville, Florida. The cover features a horizontal pair of 5-cent Green Jefferson Davis (CSA Scott 1) stamps. (Courtesy the Patricia A. Kaufmann Collection.)

Octavia affixed a horizontal pair of 5-cent green Jefferson Davis stamps to the envelope. Those stamps were ultimately tied by a double ring circular dateless postmark of “WELAKA/FLA.” In addition, an identical strike to the left exhibits the manuscript “Sept 22” date. 

Circumnavigating the inland rivers and streams of northeast Florida, known as the First Coast, the letter traversed sequentially these routes to reach its destination: Welaka to Palatka, Palatka to Ocala, Ocala to Gainesville and Gainesville to Baldwin. At that stage, the connection between Baldwin and Jacksonville was severed due to a heavy U.S. military presence. Despite resistance, the Union did, in fact, seize the St. Johns Bluff earthen fortifications on October 3.

   Taking up arms against the federal government, Octavia’s older brother, Davis H. Bryant, had enrolled on May 16, 1862 as a private in Captain Robert H. Harrison’s Independent Company of Cavalry (Amelia Island Guerrillas), Florida Volunteers.

Combat ready, Bryant – who survived the war (Figure 8) – soon found himself encamped approximately 20 miles north of Jacksonville at Hart’s Road Station in the present-day town of Yulee. Utilized as a Confederate military supply depot, Hart’s Road Station functioned primarily as a waypoint for the Florida Railroad Company, from Fernandina to Cedar Key.

Figure 8. A postwar photograph of Davis Hall Bryant that shows him later in life. (Courtesy The Confederate Veteran, January 1915)  

 Bryant’s mother, Rebecca Hathorne (Hall) Bryant, wrote to her son on November 8, 1862, from Rose Cottage. The associated cover (Figure 9) displays a double ring circular date postmark of “WELAKA/FLA.” with manuscript “Nov 9” and matching handstamp of “PAID.” There is a visible manuscript “Paid 10 cts.” (at top right) as well. Within a matter of weeks, the Amelia Island Guerrillas would be merged into the Second Florida Cavalry Regiment as K Company. 

Figure 9. A stampless Confederate cover from Rebecca Hathorne (Hall) Bryant to Davis Hall Bryant at Hart’s Road Station (Yulee, Florida). (Courtesy John L. Kimbrough MD / csastamps.com).

In accordance with Special Order 1487, Stephens’ unit was authoritatively designated Company B of the 2nd Florida Cavalry Regiment on December 4, 1862. 

Reassigned in July 1863, Stephens and his horsemen billeted themselves at Camp Cooper, just a mile north of the Hart’s Road railway junction. 

While based at Camp Cooper, Stephens received a note from Davis Bryant, who was on detached duty in the Quartermaster’s Department in Lake City. Evidently short on stationery, Bryant fabricated a makeshift envelope from a surplus roll of wallpaper for his communiqué (Figure 10). Once all flaps are fully exploded, this wallpaper adversity cover reveals a lovely multicolor floral design in varying shades of blue, red and tan. Lacking a postmark, there is merely a manuscript “Paid 10” discernible on the cover's exterior. 

Figure 10. A Confederate wallpaper adversity cover from Davis Hall Bryant to Winston J. T. Stephens at Camp Cooper in Yulee, Florida. Only approximately one dozen of such Florida wallpaper covers are recorded. (Courtesy the William J. Stier Collection) 

At the Battle of Olustee, also known as the Battle of Ocean Pond, which was fought in Baker County on February 20, 1864, Stephens proved to be equally adept at maneuvering with the main Confederate army as he and his troopers fought on foot alongside veteran infantrymen to break the advancing federal alignment. Forewarned of the Union Army’s objective to seize the Florida capital at Tallahassee, Confederate Brigadier Generals Joseph R. Finegan and Alfred H. Colquitt made emergency troop dispositions that led to the overwhelming defeat of Union Brigadier General Truman Seymour and his mixed force of white and Black servicemen. 

Two days prior to the battle, Stephens sent a penciled message to Octavia at her residency in exile in Thomasville, Georgia (Figure 11). Octavia and her children had fled Welaka on September 6, 1863 to escape the oncoming Union forces.

Figure 11. A Confederate cover from Winston J. T. Stephens to Octavia L. (Hall) Bryant dated Feb. 20, 1864. This cover is franked with a 10-cent blue Jefferson Davis (CSA Scott 11, Type I, stamp). (Courtesy the Stephens-Bryant Family Papers, University of Florida)

Simply folding this letter, Stephens attached a 10-cent Blue Jefferson Davis stamp to it. In due course, the stamp was tied by a circular date postmark of “LAKE CITY/FLA. FEB 20.” Over the river and through the woods, that letter traveled from Lake City to Tallahassee and then on to Thomasville before Octavia got hold of it. 

On March 1, 1864, Stephens led a patrol toward the city of Jacksonville in order to probe the existing Union defenses. Venturing through the forest, Stephens soon met with opposition from an amalgamated assemblage of Northern soldiers. Guns at the ready, Stephens forged ahead with his cavalry in columns of four. Veering to the east of Cedar Creek, the captain guided his horsemen into the brush where a party of Union soldiers lay in ambush. A conspicuous figure astride his dapple gray charger, Stephens paused briefly to adjust his troop formation only to be singled out by a federal sniper who mortally shot the captain through the back. 

First Sergeant Swepston B. W. Stephens of Company B, 2nd Florida Cavalry Regiment, had accompanied his older brother into the woods at Cedar Creek.  Devastated by his personal misfortune, Sergeant Stephens subsequently wrote to his brother’s widow and described the captain’s final moments:

“You know not the anguish of my heart when he was shot.  We were side by side and tho’ I was not looking at him when the fatal ball pierced him I heard it and turned and asked him if he was hurt.  He turned and looked the reply but could not speak and just at that time my spur was cut off and consequently he fell before I could reach him.  I dismounted and took him up and sit him on my horse and got up behind him and took him out in that way leaning back against me.  That look, the last look was full of love.  His lips moved but no word escaped.  I see that look now and ever will….”  

In the aftermath, Stephens’ body was transported to the Lake City Cemetery for burial beside the Confederate casualties from the Ocean Pond Battle. 

With financial assistance from the state, Stephens was reinterred in the Westview Cemetery in Palatka in 1888. Having never remarried, Octavia Stephens remained devoted to the memory of her husband until her death on September 6, 1908. During a private ceremony, Stephens’ remains were moved to the Stephens family plot at Oakwood Cemetery in Welaka in the year 2000. 

Resources

Bearss, Edwin C. “Military Operations on the St. Johns, September-October 1862 (Part I): The Union Navy Fails to Drive the Confederates from St. Johns Bluff,” Florida Historical Quarterly XLII, no. 3 (January 1964).

Bearss, Edwin C. “Military Operations on the St. Johns, September-October 1862 (Part II): The Federals Capture St. Johns Bluff”. Florida Historical Quarterly XLII, no. 4 (April 1964).

Blakey, Arch F., Lainhart, Ann S. and Stephens Jr., Winston B., editors. Rose Cottage Chronicles: Civil War Letters of the Bryant-Stephens Families of North Florida (Gainesville, Florida: University Press of Florida, 1998).

Briggs, Deane R., M.D. Florida Postal History During the Civil War (Lincoln, Delaware: Confederate Stamp Alliance, 2018).

The Confederate Veteran, XXIII, no. 1 (January 1915)

Harrison Jr., George P., “The Battle Of Olustee,” The Confederate Veteran XXIV, no. 8 (August 1916)

Jaronski, Stefan T. “The Postal Routes of Confederate Florida,” The Confederate Philatelist XXXVII, no. 1 (January-February 1992). 

Jaronski, Stefan T. “The Postal Routes of Confederate Florida, Part 2,” The Confederate Philatelist XXXVII, no. 2 (March-April 1992).

Lera, Thomas M. “Florida Confederate Railroad Mail,” Florida Postal History Society, Tallahassee CSA, mid-year meeting (2017).

The Stephens-Bryant Family Papers, Special and Area Studies Collections, George A. Smathers Libraries, University of Florida, Gainesville.

United States War Department, War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies (1880-1901), Seventy Volume Compendium in One Hundred and Twenty-eight Parts, Government Printing Office, Washington, D.C. 

Winston J. T. Stephens Collection, Museum of Florida History, Tallahassee.

The Author

A native Kentuckian, William J. Stier is currently writing a full-length book about Captain Winston Stephens and the St. Johns Rangers in Northeast Florida. Mr. Stier may be reached by e-mail at: kycavalier@att.net 

For Further Learning

Recommendations from the APRL research staff:

Briggs, Deane R. “Confederate Covers to Small Florida Towns” Florida Postal History Journal, January 2009. 

Briggs, Deane R. Florida Postal History During the Civil War (United States Of America, Confederate Stamp Alliance, 2018). [G3931 .P856 B854fc 2018]. 

Herst, Herman, Jr. “Florida History Archives Valuable Resource for Postal History,” Confederate Philatelist, March-April 1993. 

Jaronski, Stefan T. “Postal Routes Of Confederate Florida,” Confederate Philatelist, January-February 1992.

John W. Kaufmann Sales. William G. Bogg Collection of Florida In the Confederacy February 21, 1987. Sale 128. (Washington, DC: John W. Kaufmann Sale, 1987). [NS Bogg, William G.]

McNeal, Herbert P. “Florida In the Confederacy” Mekeel's Weekly Stamp News, May 13, 1994. 

Robert A. Siegel Auction Galleries. Florida In the Civil War, The Deane R. Briggs, M.D. Collection May 9, 2017 (New York, NY: Robert A. Siegel Auction Galleries, 2017). [NS Briggs, Deane R.] 

Stets, Robert J. “Confederate Post Offices in Florida,” The Heliograph, Winter 1989.