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In September 1861, a schooner called the ''William H. Judah'', of which the Confederacy had contracted the use, ran the Union blockade and successfully entered Pensacola's harbor, docking at the navy yard. When it became apparent to Union forces that the Confederacy was attempting to outfit the ''Judah'' as a [[Wikipedia:Privateer|privateer]], they developed a plan to sabotage the work. In the early morning hours of [[September 14]], a Federal raiding party of about 100 sailors and marines in four small boats cast off from the ''[[Wikipedia:USS Colorado (1856)|USS Colorado]]'' bound for the ''Judah''. Approaching the vessel at around 3:30 AM, they were greeted with musket fire from Confederate guards; however, the raiding party successfully boarded the ''Judah'' and set it aflame. The raiding party also managed to spike a gun battery at the navy yard before retreating. The small clash resulted in three deaths apiece on both sides, the first of the war in Florida, as well as several wounded.<ref name="PICW" /><ref>[http://www.flheritage.com/archaeology/projects/shipwrecks/legacy/shipwreck.cfm "U.S. Navy and Confederate Shipwreck Project."] ''Florida Division of Historical Resources''.</ref>
In response to the attack on the ''Judah'', Confederate general Braxton Bragg ordered an attack on [[Fort Pickens]]. A force of over 1,000 men under general [[Wikipedia:Richard H. Anderson|Richard H. Anderson]] set out from Pensacola on the evening of [[October 8]], landing on [[Santa Rosa Island]] about four miles east of Fort Pickens. From there the Confederate troops were divided into three groups: one which travelled on the north (Sound) side of the island, one which travelled on the south (Gulf) side, and a third which trvalled just behind both, used as a flank to connect the groups. After marching for three miles, the Confederate troops were spotted by an encampment of the [[Wikiepdia:6th Regiment of the New York Volunteers Volunteer Infantry|6th New York Volunteer Infantry]] and fired upon. However, the Confederate troops had the element of surprise and quickly overwhelmed the encampment, sending the 6th New York retreating back to Fort Pickens. Soon after, though, the Confederate general Anderson decided to retreat, during which Union forces pursued and caused extensive casualties. The retreat is described in the ''Florida Historical Quarterly'' article, "Pensacola in the Civil War":
{{cquote|As dawn was rapidly approaching, and the fort and batteries were alerted to his assault, [Anderson] abandoned his plans for any further attack and ordered his troops to march back to their original point of debarkation.
In their hasty retreat, the Southerners found themselves being outflanked. As they were boarding the steamers, flats, and barges, the well trained Union infantry took careful aim from behind the closest dune ridge and showered the Confederates with large quantities of effective musketry that caused considerable death and injury. Florida's first major land battle ended when the steamers left the island for Pensacola. The Confederates reported a loss of 18 dead, 39 wounded and 30 missing or presumed prisoners of war. [Union commander] Colonel Brown stated his losses as 14 dead, 29 wounded and 24 prisoners.|20px|20px|"Pensacola in the Civil War." ''Florida Historical Quarterly'', Vol. IX, No. 2, 1978.}}
==Artillery exchanges==
A series of artillery battles took place during late 1861 and early 1862. On [[November 22]] and [[Novemner 23|23]], 1861, Union and Confederate positions exchanged artillery fire over Pensacola Bay; Union troops expended 5,000 rounds of ammunition while Confederate troops returned some 1,000 shots. Fort Pickens on the Union side sustained little damage, but Confederate-held [[Fort McRee]], its water battery, as well as the navy yard and the village of [[Warrington]] all sustained extensive damage. Federal troops did sustain two deaths and 13 wounded. Federal artillery inflicted even more damage on [[January 1]] and [[January 2|2]], 1862, causing extensive fire damage at the Navy Yard and exploding the powder magazine at [[Fort McRee]].<ref name="PICW" />
==Pensacola surrenders==
The Union invasion of Tennessee in early 1862 necessitated Confederate reinforcement and on [[March 19]] around 8,000 Confederate troops left Pensacola for Tennessee, leaving behind only a token force. Confederate Colonel Thomas M. Jones was left in command at Pensacola surrendered and authorized to U.Suse his own discretion concerning the evacuation of the city. troops Upon learning on [[May 107]] that Union commander [[Wikipedia:David Farragut|David Farragut]]'s fleet was anchored off [[Mobile Bay]], Colonel Jones quickly removed most of the Confederate artillery and supplies from Pensacola. The last Confederate troops to leave, on [[1862May 9]], and most set fire to the remnants of the city was burnedNavy Yard and other Confederate defenses. Almost all Most Pensacola residents evacuated inland to Greenville, Alabama.<ref name="PICW" /> Pensacola, left in the hands of acting Mayor [[John Brosnaham]], surrendered to U.S. troops under Lieutenant Richard Jackson on [[May 10]]. That evening, Union troops raised the stars and stripes over [[Plaza Ferdinand VII]].<ref name="PICW" />
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