In the months following the September 1863 expedition to Bayport, between October and December, the East Gulf Blockade Squadron reported on the capture of numerous vessels that were from Bayport.  While many of these vessels were British vessels they were supporting the Confederacy by carrying cargo from the many ports along the Gulf Coast, including Bayport.  

According to an October 20, 1863 report filed by Acting Ensign, James S. Williams, from aboard the U.S. Schooner Annie while at sea some 20 miles W.S.W. of Bayport, they were reporting the capture of a schooner containing a very large cargo of sea-island cotton.  It was further reported that the vessel captured was the British schooner Martha Jane, which was under the command of Captain H.C. Winslow of Bayport.  Along with Captain H.C. Winslow were 5 crew members who were all detained by the Union Schooner Annie while their cargo containing 26,609 pounds of sea-island cotton was seized, this was one of the largest captures of Bayport cargo documented.  Once seized, with its crew, cargo and the British Schooner Martha Jane in tow, the East Gulf Blockade Squadron's Schooner Annie proceeded to Cedar Keys where they would delivery their prize capture to Leuitenanct-Commander E.Y. McCauley.

Henry Clay Winslow, pictured left, was born in Washington County Maine on February 18, 1836.  Henry Clay's ancestry dates back to Edward Winslow, who was the first governor of the Plymouth Colony and the family is said to have traveled to this country on the Mayflower.  His father, Jacob Winslow, was a sea captain who sailed the Atlantic for many years.  At the young age of thirteen Henry Clay went to sea and held every position from cook to captain.  Henry followed the sea for nearly 10 years when sometime in the 1850's he experienced a hurricane off the coast of Cuba where his ship was capsized and sunk.  After he returned to Maine and engaged in the mercantile business in Plymouth.  By 1857 Henry Clay had moved his mercantile business to New Orleans and at the outbreak of the Civil War he found himself with large business interest while endeavoring to remain neutral in the war.  Winslow finally gave up his large business interest and secured permission from his dear friend General Braxton Bragg to accompany the Army of Tennessee where he devoted a portion of his time in assisting the chief medical director of General Bragg's staff in caring for the wounded from battle.  At the battle of Stone River, Winslow had his horse shot from under him.  After that experience Winslow decided it was time to leave "Dixie" and he headed south to once again become captain on the sea.  At Bayport, Winslow found the large British Schooner Martha Jane for sale.  For the price of $40,000 Winslow purchased the schooner with the purpose of running the Federal blockade.  Captain Winslow loaded his schooner with a large load of the finest sea island cotton, weighing over 26,000 pounds.  In Havana this sea island cotton could be sold for $1.00 per pound in gold.  As we already know, Winslow's schooner was overhauled by the Union Schooner Annie and the cargo confiscated.  During confiscation Winslow was reluctant in giving up his suspenders in which he had concealed and sewn $2,000 worth of $20.00 gold pieces, meant to be used upon release.

While the capture of these cargo vessels many times seems uneventful it must be kept in mind that these cargo schooner had no means of defense.  With no defense these cargo vessels would many times attempt to flee, which would result in chase by the Union boats.  On October 28, 1863 this would be the very case as the crew of a different British vessel bound for Bayport attempted to run the Union blockade to prevent capture.  Following orders, the launches of the U.S.S. Sagamore consisting of its gunboat, a launch boat and the Schooner Annie, set sail from Cedar Keys to cruise of Bayport and Crystal River to intercept any vessels attempting to enter or leave from those places.  At. about 3 p.m., with a northward sail, and intentions to reconnoiter the harbor at Bayport, the Schooner Annie and launch boats discovered a sloop standing to their southeast.  The gun boat was immediately sent to the northeast in order to intercept the sloop's entrance into Bayport as the Schooner Annie followed to the outside preventing the sloop from running out to sea.  As the sun began to set the Schooner Annie lost sight of the sloop and the crew set anchor to await the return of the launch boats that were still giving chase to the sloop.  During this time the Sagamore's gun boat had given chase to the sloop as she made her way towards Bayport.  As the Sagamore's gun boat gained on the sloop, pulling within three quarters of a mile of its position, they fired three shells with two exploding close to the fleeing sloop.  With the only defense of escape, the sloop and its crew paid no attention to the shelling and continued on a steady course.  The Sagamore's gun boat eventually lost sight of the sloop as the sun began to set and heavy squalls began to roll in off the Gulf.  Being too dark to locate the position of the Schooner Annie, the Sagamore's gun boat anchored just outside the Homossassa River and awaited daylight.

At daylight on the morning of October 29, 1863 the Sagamore's gun boat once again began to patrol along land in hope of find the sloop that they had given chase the night before.  Not seeing any signs of the sloop they returned to the Schooner Annie arriving at about 8 a.m.  Resting for the better part of the day, at 4 p.m. the Sagamore's gun boat took the launch and stood in for Bayport.  As the launch boats cruised up towards Bayport they proceeded close enough to check the harbor for the sloop and any other vessels.  As the rebels discovered their approach the Confederate flag was hoisted on the Bayport battery.  With the discovery of no vessels in the Bayport Harbor, the launch boats returned to the Schooner Annie at about 7:30 p.m. and anchored for the night.

At 7:30 a.m. on October 30, 1863 the Schooner Annie, the Sagamore's gun boat and launch situate 30 miles southwest from Bayport discovered a sail on the horizon to the southwest of their position, it was none other then the elusive sloop from two days prior.  The Sagamore's gun boat immediately set to intercept the sloop's entrance into Bayport while the Schooner Annie got underway and stood for the sloop itself.  By 11 a.m. the weather and the seas began to calm and the Sagamore's gun boat hauled up and stood for the chase of the sloop.  By 3 p.m. the gun boat came within range of the sloop and immediately fired a shell, the sloop finally gave in and the chase was over.  As the captured vessel lowered her jib, Acting Ensign, Commanding, James S. Williams, of the Schooner Annie, boarded the sloop.  The captured sloop actually proved to be the 29-ton British Schooner Meteor from Havana in charge and owned by Captain Anthony Bado.  The captain claimed that he was taking his assorted cargo to St. Marks, Fla., however he was cleared for Matamoras located no where near St. Marks.  The cargo, vessel and crew were immediately seized by the East Gulf Blockade Squadron.  The Schooner Annie turned the captured vessel over to the launch, which made sail for Cedar Keys with the Schooner Meteor and its assorted cargo in tow.  Once to Cedar Keys the prize capture would again be turned over to Leiutenanct-Commander E.Y. McCauley.


The capture of these Confederate Blockade runners proved to be very rewarding and successful venture for those Union officers who had the pleasures of participating.  As a result of these captures many officers of the East Gulf Blockade Squadron became wealthy men from these ventures.  According to the U.S. Prize Laws, one half of every prize or capture went to the Government while the other half was divided among the officers and seamen of the capturing fleet, which was added to their monthly pay.  This prize law also encourage the capturing fleets to increase their activities and capture more prizes and vessels.  In December of 1863 with the increased activities in blockade running the U.S. Navy was making preparation to add a new steamer to the East Gulf Blockade Squadron.  Consisting of the Steamer Nita preparations were to have the new steamer cruise an area between Bayport and the Suwanee River, however the steamer was stationed in Key West for repairs.  This steamer's armament consisted of one rifled 12-pounder howitzer, in pivot, forward; two heavy 12-pounder howitzers, in broadside, forward; one smooth 24-pounder howitzer, in pivot, aft. with a compliment of officers numbering 46.  It is believed that this steamer was never commissioned for the Bayport area but if so this steamer alone could have caused significant damage to Bayport with its number of large guns and pivot howitzers.


1864 and the Brooksville-Bayport Raid
While the East Gulf Blockade Squadron was actively involved with the blockading of Bayport and the coast, there was still an excessive amount of beef that was making its way to the Confederate Troops.  By the end of 1863 there were a number of local home guards between Tampa and Hernando County that were engaged in herding beef cattle for support of the Confederate Army.  In addition to the local home guards there were also special details and orders from the front lines for the assistance in the gathering of the beef cattle from the area.  Among these special details was one from the company of Capt. Walter T. Saxon's Hernando Wildcats, who at the time were in battle at Missionary Ridge.  The Chief Commissary of Florida had made a requisition on General Bragg for sixty Florida men to report to the plantation of James McKay Sr., at Tampa, for the purpose of gathering beef cattle for the Western Army.  Among the men listed for this detail was Brooksville resident Thomas Benton Ellis of Saxon's Company.  As the sixty men gathered at the home of McKay in Tampa they organized into a company with Captain James McKay Jr.; Fist Lieutenant W.W. Wall, Second Lieutenant John W. Crighton, and First Sergent Thomas Benton Ellis.  This company at once began to gather beef cattle from all parts of South Florida, driving them north to Live Oak where they were shipped to Bragg's Army [Confederate] and the front lines.

According to one detailed military reports, Capt. James McKay's company was in charge of gathering cattle south of the Withlacoochee River with his headquarters at Brooksville.  In addition to McKay's company having headquarters in Brooksville, there was also now the added support of Capt. Leroy Lesley's Homeguard's who had been orginized and muster into service only a few months prior.  According to one Union report Capt. Lesley's Company numbered 80 and was classified as being Infantry situated near Brooksville.  It would be Capt. Leroy Lesley's Home-guards who would provide the area with much need picket lines to protect and defend Brooksville from any raiding Union troops.   According to these reports there was approximatly 450 Confederate men patroling the areas between Brooksville and the Pease Creek in Hillsborough County during 1864.

With the gathering of beef cattle throughout Florida and the blockading of goods along the coast, many Hernando County residents found it difficult to find the necessities of everyday life including food.  Things became so bad for the residents of Hernando County that on many occasions people were made to give up their last bit of corn and milk or beef cow to support the wartime efforts.  As a result some residents had very little sustenance during the Civil War and faced near starvation.  In January of 1864 the Hernando County Board of County Commission met to discuss the crisis of no food for residents.  The Board of County Commissioners further directed the Hernando County Probate Judge, Perry G. Wall, to draft and send a letter to then Florida Governor John Milton.  This letter outlined the desperate need of food for the residents of the county and stated that the McKay detail had stripped the country of cattle.  This letter further asked for the help and support of the State of Florida during Hernando County's time of need and read as follow:

Late 1863 to early 1864 plans for a joint expeditions between the U.S. Army and the U.S. Navy was being planed and orginized.  At the request of Union Brigadier-General Daniel P. Woodbury, commanding the U.S. Army in the Key West District, Acting Master's Mate Henry A. Crane, from aboard the Sloop Rosalie, was ordered to report to the General for temporary duty connected with the United States Army.  General Woodbury was in the process of organizing a company of refugee rangers to cooperate with some of the troops under his command, for the purpose of an expedition.  The purpose of the expedition was to prevent the supply of beef cattle being sent to the rebel army from the region of Tampa.  It was reported that between 1,500 to 2,000 beef cattle were being sent from the Tampa Bay region per week by Capt. McKay's Company with headquarters in Brookville.  These beef cattle were much needed food support for Bragg's Confederate Army.  While the cattle was much needed food for General Bragg's Confederate Army, it was also much needed food for the residents of Hernando County.  Subject to the approval of the U.S. War Department, General Woodbury proposed the appointment of Henry A. Crane as the Captain of his company of refugee rangers that was being formed.  General Woodbury believed that Crane's experience in military matters was to be of great service to the expedition in preventing the the supply of beef cattle to the Confederate Army as planned.

Soon after the forming of General Woodbury's company of refugee rangers, in January of 1864, this small company would carry out an expedition of the Charlotte Harbor south of Tampa, however the Charlotte Harbor expedition proved to be a trying one on the General's new company of refugee rangers.  Following the Charlotte Harbor expedition, General Woodbury and the 47th Regiment Pennsylvania joined the refugee rangers and proceeded to establish a U.S. Military Post at Fort Meyers.  According to a Theodorus Bailey, Acting Rear Admiral  and Commander of the East Gulf Blockade Squadron, the expectation of receiving recruits for the refugee rangers from the surrounding country has not been justified by the event; speaking of the Charlotte Harbor expedition.  Bailey writes that only a month had passed when six of the already enlisted had deserted to the enemy [Confederates] and had combined with them to attack our men [Union].  Bailey adds that these circumstances occurred before the arrival of the General and that the defection appeared to have been arranged before leaving Key West to carry out the expedition.  Bailey also recommended that the support of a much larger force, than could possible be spared, to produce any important results.

In addition to the formation of the refugee rangers company was the formation of the 2nd Florida Calvary, a Union Regiment comprised of companies such as the refugee rangers formed at the direction of General Woodbury.  The 2nd Florida Calvary enlisted into the U.S. Army in December of 1863 in Cedar Keys, around the same time the company of refugee rangers was formed.  Service duty of the 2nd Florida Calvary would be in Fort Meyers, Cedar Keys, and the district of Key West.  While in service at Fort Meyers the 2nd Florida Calvary would enlist more supporters, including numerous residents from Hernando County who had abandoned their Confederate ways and joined the Union under Companies A and B of the 2nd Florida Calvary, among these residents was former Hernando County Probate Judge Samuel J. Pearce.  Those Hernando County residents who joined Companies A and B of the 2nd Florida Calvary were neighbors of those families who supported the Confederate movement in Hernando County.  Between February and May of 1864 the numerous companies formed under the 2nd Florida Calvary would carry out numerous expedition including raids on Tampa and the Pease Creek.

By May of 1864 preparation were underway by General Woodbury of the U.S. Navy to conduct a raid on Brooksville.  As preparation were being made for the Brooksville expedition, Acting Rear Admiral and Commander of the East Gulf Blockade Squadron, Theodorus Baily, issued the orders to the navel vessels under his command to place themselves under General Woodbury for the purpose of cooperating in an expedition planned by him against the enemy.  These orders further gave General Woodbury command of vessels that would carry his troops.  On May 2, 1864 the following naval vessels were ordered under the command of General Woodbury to carry out an expedition planned for Brooksville.  Again this expidition was the cut the supply of beef cattle coming from the area and being sent to Bragg's Confederate States Army.