Brooksville, Florida
Named for Rep. Preston
Brooks, who used his walking
stick to beat an opponent on
the floor of the U.S. Senate,
Brooksville is a charming city. - Brooksville Raid, Florida - Brooksville Raid, Florida
Brooksville Raid
A Confederate monument stands in front of the
Hernando County Courthouse in Brooksville. The
town was the target of a Civil War raid.
The Brooksville Raid
A massive outdoor mural in
Brooksville depicts Civil War
fighting on a large scale.
May-Stringer House
The original section of this
beautiful house in Brooksville
was built in 1855 and
survived the Civil War. The
home was enlarged in 1903.
Historic Bayport, Florida
A Brooksville Raid ended
here at Bayport on the Gulf
Coast, where Union ships
evacuated the Federal
The Brooksville Raid - Hernando County, Florida
A Civil War Encounter in Florida
The Brooksville Raid was an incursion that
Union troops launched into Hernando
County, Florida, during the Civil War. It is
commemorated annually by what is called
the largest Civil War reenactment in Florida.

Although official documentation regarding the
expedition is sparse, Captain Henry Bowers,
a staff officer in Key West, reported that the
raid began on July 1, 1864, when 240 men
boarded transports at Fort Myers, Florida:

On the 1st ultimo, an expedition, consisting of
120 men of the Second Florida Cavalry and
120 men of the Second U.S. Colored Troops,
total 230, the whole under the command of
Capt. J.W. Childs, Second U.S. Colored
Troops, embarked from Fort Myers, Fla., for
Bay Port, on the west coast.

Coming off their vessels, the Union soldiers
started inland for Brooksville. The town had
been founded in the early 1840s and was a
center of commerce for the surrounding
communities and farms. As the troops
moved along the road leading to Brooksville,
they confiscated livestock, grain, provisions
and other supplies, often setting fire to barns,
smokehouses, corn cribs and even houses
as they passed:

...On landing, the enemy's pickets were
discovered and skirmishing commenced.
Our troops followed the enemy into the
interior to Brooksville, a distance of 40 miles,
occasionally skirmishing with them. Seven
prisoners and 15 horses were captured, and
13 contrabands (i.e. captured slaves)
brought in. The plantations of Captain Hope,
Captain Leslie and sons, and Captain
Hooker, all commanding guerrilla parties of
the enemy, were destroyed.

As the Confederate pickets retreated ahead
of the oncoming Federal raiders, they sent
word to Brooksville for the men there to
assemble. There were a few soldiers in the
area from Captain Charles J. Munnerlyn's 1st
Battalion of Special Cavalry, Florida's famed
"Cow Cavalry." This unit defended the large
cattle herds in South Florida and assured the
safe movement of beef north to the Southern

As the scattering of soldiers and volunteers
assembled on the hill at Brooksville, possibly
the one now occupied by the Hernando
County Courthouse, couriers were sent to
alert Captain James McKay and L.G. Leslie,
who were then at Tampa Bay. Both men were
serving with Munnerlyn's Battalion, although
McKay was actually an officer in the Fourth
Florida Infantry.
While the couriers rode off for Tampa, the few
dozen men at Brooksville headed out to meet
the Federals. Taking position behind a creek
or branch, they waited for the enemy to arrive.

The expected battle never developed. The
two forces skirmished with each other,
primarily firing shots at long range, but the
Union soldiers were more interested in
foraging than fighting. After reaching the Ellis
Plantation, which they thoroughly ransacked.

After eating their meal at the Ellis place and
then setting fire to the outbuildings and even
the house (which was saved by a Union
soldier who knew the family), the Federals
turned and marched for
Bayport on the coast.
The ragtag assembly of Confederates
followed, skirmishing with the rear of the
Yankee column.

The Federals captured 60 bales of cotton at
Bayport, but most of it was accidentally
burned despite hopes of loading it aboard
the navy ships waiting there. After doing what
other damage they could to the little port
town, they returned to their transports and
steamed back to Fort Myers. Only one Union
soldier was reported wounded in the entire
episode. Seven Confederates were captured.

Brooksville is know known for its beautiful old
homes and oak shaded streets.
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Copyright 2011 by Dale Cox
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