The Bloodiest Place in Florida Territory

South of Gainesville at the corners of Alachua, Marion, and Levy County was the bloodiest place in Florida during the Second Seminole War. More battles and skirmishes happened in this area than any other place during the entire duration of the war. Just because the Seminoles were moving further south did not mean that this area calmed down. The road that went from Micanopy southwest to Wacahoota should be renamed "the bloody road" because of all the killings that happened there. The first and last soldiers who died in this war were killed near Wacahoota. Here is a list of some of the battles and skirmishes in the region:

San Felasco, northwest of modern Gainesville:

West of Paynes Prairie: Wacahoota area, near where Alachua, Marion, and Levy counties meet: Micanopy, at the modern town of the same name: Near Orange Lake: Fort Drane, northwest Marion county: Fort King, modern Ocala near Silver Springs:

The Battle of Bridgewater

It is surprising that one of the bloodiest battles of the Second Seminole War on May 19, 1840, has been almost forgotten in the pages of history. Comparing the list of regular Army soldier deaths, this battle ranks fourth in number of killed by Indians during the war.

The military road between Forts Micanopy and Wacahoota was the deadliest place during the Second Seminole War. By 1840 the war was extremely unpopular with no end in sight. All negotiations had failed, even when the Secretary of War himself came down to Florida and negotiated a treaty that soon failed.

On May 19, 1840, Lieutenant Martin of the 2d Infantry with three men from Fort Wacahoota were passing on the Micanopy-Wacahoota Road when they were ambushed and fired upon by Seminoles. One soldier is killed and the other two were missing. Although listed as mortally wounded, Lt. Martin escapes to Fort Micanopy.

James S. Sanderson was a non-commissioned officer in the 7th Infantry Regiment who was highly recommended by the officers and appointed Second Lieutenant on March 1, 1838. By 1840 he was commanding Fort Micanopy. He leads a party of 18 men from Micanopy to search for the Indians in the area of the ambush. Bloodhounds are taken to track the Indians.

Searching for the hostiles, the army command sees a distant fire in the woods. It is possible that the fire was set on purpose to lure the soldiers into an ambush. Suddenly they are surrounded by a large party of Indians "near Bridgewater". This attack may have been by Miccosukees under Halleck Tustenuggee, who was known to have made similar attacks in this area during the same year.

Being outnumbered and seeing little way out, Lieutenant Sanderson with 13 men charge the Indians. Lieutenant Sanderson, nine soldiers, three bloodhounds and their keeper are killed. Principal Musician Patrick O'Riley is killed while fighting by Sanderson's side. Four men are missing. Lt. Sanderson is horribly mutilated, with his fingers cut off and stuck in his mouth.

Unmentioned are about 2 other soldiers whose fate is unknown. It is possible that they escaped to get help, because Private Owen Cowley is listed as dying several months later from wounds received in the battle.

Sergeant Major Francis Carroll is wounded but survives alone at the site of the battle until the next morning when Lieutenant Colonel Riley, 2nd Infantry Regiment, arrives to remove the dead. Ironically, Carroll is killed seven months later in a similar deadly ambush at the Battle of Martin's Point (below).

Known names of those killed (Regular Army):

2nd Inf. Reg., Co. K: Sgt. Philo C. Griggs--killed; Pvt. Calvin Hotchkiss & Pvt. Patrick Jeffers--killed or taken prisoner by Indians.

7th Inf. Reg.: 2nd Lt. James S. Sanderson, Co. C; Pvt. Owen Cowley, Co. F (died January 5, 1841 from wounds); Pvt. William Foss, Co. H; Pvt. Henry Keefe, Co. I; Pvt. Abraham Maxwell, Co. I; Prin. Musn. Patrick O'Riley; Musn. Samuel Okey, Co. I.

"A great sheet of flame leaped from the roadside."
from "Through Swamp and Glade, A Tale of the Seminole War," by Kirk Munroe, New York, Charles Scribner's Sons, 1896.

The Battle of Martin's Point

One of the deadliest places during the Second Seminole War was the road between Micanopy and Wacahoota. Many incidents happened here, where the Indians would use the surrounding hammocks to ambush anyone who passed by. One of the couriers, Benjamin Finklepaugh, wrote from Micanopy about that area in August 1840:

"I know it is dangerous, but I have got so used to it, I think nothing of it anymore ... if you had seen as many folks cut up by the Indians, you would have got used to." (From "Alachua County, A Sesquicentennial Tribute" by John B. Opdyke.)

One of these bloody attacks happened on December 28, 1840. Lieutenant Sherwood left Micanopy and headed southwest to Fort Wacahoota. Riding with this escort was also Mrs. Montgomery, wife of Lieutenant Montgomery at Micanopy, who had been married only three weeks. The rest of the party was made up of Lieutenant N. Hopson, Sergeant Major Carroll, ten privates, and a wagon with five mules. The area had been quiet recently, so they were under a false security. Lt. Montgomery was sick and not able to accompany his wife on the Sunday ride.

They had gone about 4 miles when they reached Martin's Point. (I believe this was named after Lt. Martin, who was attacked here before the Battle of Bridgewater.) Within twenty yards from a hammock, they were fired upon; two privates were killed. Lieutenant Sherwood rallied the group to defend themselves. He persuaded Mrs. Montgomery to dismount and get into the wagon, when she was shot in the breast. Panic ensued; the mules became entangled in the harness, and were killed on the spot. Lieutenant Hopson returned to Micanopy for reinforcements. Lieutenant Sherwood and the remaining party fought hand to hand with the advancing Indians. After much fierce fighting and exhausted from loss of blood, Lieutenant Sherwood fell with Sergeant Major Carroll fighting at his side. The Indians scalped and mutilated the bodies. Private Burlingham, alone and wounded, protected the body of Mrs. Montgomery from "the merciless barbarities of the savages, who gathered around her, determined to gratify their diabolical revenge."

The attacking party consisted of 30 Mikasuki warriors under Halleck Tustenuggee and Cosa Tustenuggee. Later Indian accounts said that one of the warriors was mortally wounded, and Lieutenant Sherwood died while fighting to the death with another. The viciousness of the attack disturbed Cosa Tustenuggee so much that he surrendered at Fort King shortly after.

When troops from Micanopy arrived, the Indians were long gone. Lieutenant Montgomery was with them, to see his wife who had just been killed. The dying words of Private Burlingham were spoken to him, "Lieutenant, I fought for her as long as I could; but they were too strong for me," -- his voice here faltered -- "but I did my duty." His ear was deaf to the repeated thanks of his officer, from a heart already overburdened with grief.

Secretary of War Joel Poinsette

During his tenure in office during the Van Buren Administration, he had the unpleasant task of writing several reports to congress detailing the high cost of the war in the number of lives and dollars. Things were particularly bloody in Alachua County.

Reaction in the newspapers and from Secretary of War Joel Poinsett in Washington was immediate. Poinsett ordered a formal investigation and even trial if any responsible officers were found. The command was not following orders by being under the 30-man minimum for all patrols in the area. The infantry soldiers were mounted on horses, which was another violation of orders, because they could not control the horses and defend themselves at the same time if attacked.

List of those killed (all soldiers with 7th Infantry Regiment): Second Lieutenant Walter Sherwood, Private Lansing Burlington, Sergeant Major Francis Carroll, Private Alexander McDonald, Private John R. Smith, and Mrs. Montgomery.

On January 22, 1841, a fort was established on the Peace River, named Fort Carroll after the fallen Sergeant Major.

A few months earlier a Methodist minister was killed at this very same location, and buried here. It is very likely that he is still buried here, but it would now probably be an unmarked grave. If we can locate Martin's point, there are reenactors who portray the 7th Infantry soldiers who died here that would like to hold a memorial ceremony. And if possible, even make a new memorial or grave marker.


Sometimes researching the Seminole war can be difficult. Several different accounts of the same event can give a completely different story. Using some of the versions of the same story, I have reconstructed the incident at Hickory Sink into quiz format. All the answers are taken from accounts written in the 19th century.

On June 19, 1835 an event happened west of Hogtown (what is today Gainesville) known as the incident at Hickory Sink. Several militia soldiers with the Spring Grove Guard (but not on duty at the time) came across a group of Indians at a place known as Hickory Sink. This was north of the reservation boundary.

1. How many Indians did the militia soldiers find there?

2. What were the Indians doing at the time? 3. What did the whites do to the Indians?
4. More Indians arrived, saw what was happening, and fired upon the whites. How many Indians were with this new group?
5. Shots were freely exchanged between the two groups and both sides broke off and went their separate ways. How many of the militia soldiers were wounded? 6. How many of the Indians were killed and wounded? Osceola complained to Indian Agent Wiley Thompson at Fort King that whites had attacked his people. Thompson responded that the Indians were the ones who caused it, and demanded that those involved are turned over to civil authorities. The Indians involved surrendered, but were later released after the different authorities could not decide who would be the ones to hang the Indians. In August 1835 a mail carrier was killed north of Fort Brooke, and it was believed to have been revenge for the incident at Hickory Sink.

Answers: (Most acceptable.) 1=a; 2=b; 3=d; 4=b; 5=c; 6=a

Read about the Patriot War in Alachua County.

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© 1998, 2002 Chris Kimball
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