Seminole War
Boyles, Holmes and the Last Stand on the Choctawhatchee (Seminole War 200th)

Maj. Gen. Andrew Jackson, seen here late in life, sent Capt. Thomas H. Boyles to attack the Red Stick chief Holmes. National Archives

Capt. Thomas H. Boyles left Pensacola 200 years ago today to begin the final raids of the First Seminole War. He and his rangers were under orders to exterminate any Native American warriors found in Northwest Florida.

This article continues a special series that commemorates the 200th anniversary of the First Seminole War. Please click here to see the entire list of stories.

Boyles had just completed a similar operation along the Perdido River. He convinced the Muscogee (Creek) families he found there to surrender, promising them protection. It was a promise he could not keep and a band of murderers massacred them near Claiborne, Alabama (please see Slaughter of Muscogee families in South Alabama). 

The captain now turned east to target the Red Stick chief Holmes (also spelled Holms or Homes) who had lived on the Choctawhatchee River in the Florida Panhandle since the end of the Creek War of 1813-1814.

A follower of the Prophet Josiah Francis, Holmes retreated south into Spanish territory following Andrew Jackson’s bloody victory at the Battle of Horseshoe Bend. Maj. Uriah Blue targeted his first new settlement with a large military force on December 26, 1814. The town was destroyed but the chief and his followers escaped with their provisions and other supplies. The noted frontiersman Davy Crockett took part in the raid. (For more information, please see: Davy Crockett in the Florida Panhandle).

A spring on lower Holmes Creek in Washington County, Florida.

Holmes retreated deeper into the swamps and built a new village on the east side of the Choctawhatchee near today’s Washington Blue Spring. Once called the “Big Spring of the Choctawhatchee,” this beautiful natural feature located in Washington County near the point where Holmes Creek flows into the river. Surprisingly, the chief and his followers seem to have gotten along with Jonathan Bunker, an early white settler who built a home nearby.

Holmes was still living at this town roughly three years later when the First Seminole War erupted in 1817. He joined the alliance of Red Sticks, Seminoles, Miccosukees, Yuchis and maroons (Black Seminoles) that fought against the United States. His neighbor, Bunker, fled his settlement until the end of the war.

American spies reported that the chief was receiving supplies – including arms and ammunition – from the Spanish in Pensacola. This made him even more of a thorn in Andrew Jackson’s side and the general sent Capt. Boyles and his rangers on a seek and destroy mission to find and kill the Red Stick chief and his warriors.

The Choctawhatchee flows from Southeast Alabama through the Florida to Choctawhatchee Bay.

Boyles carried out three known raids between July and December 1818. The first of these began 200 years ago today on July 20, 1818, and targeted any warriors who might still be lingering along the Escambia and Yellow Rivers. This would eliminate any threats close to American territory or the U.S. occupied city of Pensacola. The rangers could then go after Holmes and his main band.

…About the 20 of July Capt. Boiles, with between 50 & 60 men of his own and McGirt’s companies &c. marched for the purpose of scouring the Escambia & Yellow Water as far as the mouth of the latter river, where I had intended to fit him out for an expedition against Holmes Town and the country to the Eastward as far as the Appalachicola. [I]

How far Boyles completed this first mission is not known. He was only in the field for nine days when orders came from Maj. Gen. Edmund P. Gaines redirecting him to Fort Montgomery near Tensaw, Alabama. Gaines wanted the rangers to escort Maj. P.H. Perrault who was to prepare a topographical survey of the Florida Panhandle. Perrault fell seriously ill, however, and the rangers returned to the field in August and soon penetrated as far east as the Choctawhatchee River.

Boyles found Holmes’ new town at Washington Blue Spring in August 1818:

The Spanish calaboza or “calaboose” where the Red Stick prisoners were held stood at the southwest corner of Alcaniz and Intendencia Streets in Pensacola. From The Peacemakers by John Appleyard.

Boyle reported to me the other day in the absence of Col. King. He has not done a great deal. He burnt Holmes Village, where he also destroyed a fine field of corn, and took not far from it eight Indians. They have been delivered in this place and are confined in the Calabooze. I thought it better than to send them to Montgomery, as I was fearful they might suffer a senseless fate like those who were sent to Claiborne. The massacre of prisoner who confide alone to your honor, deserves a more sincere punishment than the acts of a secret assassin. [II]

The ”Calabooze” was the Spanish jail in Pensacola. The reference to the “senseless fate” of those “sent to Claiborne” was to the massacre of several Muscogee (Creek) families near Fort Claiborne, Alabama (please see Slaughter of Muscogee families in South Alabama).

Giving his men a few days to rest and resupply, Boyles immediately returned to the field and by early October was back in the vast wilderness of Northwest Florida. This time he and his men moved up the Yellow River by boat examining the banks for signs of Indian activity. They discovered a fresh trail on October 6, 1818:

A recreated battle of the First Seminole War.

He reports that on the 6th inst. he left his boats in Yellow Water, and with a detachment of 22 men, on foot, pursued a party of Indians, whose trail he had discovered. He over took them on the 8th about five and twenty in number, attacked and defeated them – killing four, wounding many, and making some prisoners. – A large quantity of ammunition and all their plunder fell into his hands. [III]

The location of this battle is not known but it was somewhere near the Choctawhatchee River. There is an old legend in Washington County of a fight near Daniels Lake between Holmes’s warriors and a detachment of U.S. soldiers. Whether this was the action that took place on October 8, 1818, is not known.

What is known is that the Red Sticks were far from defeated. Gathering reinforcements, they pursued Boyles through the night and counterattacked his rangers at dawn on the morning of October 9, 1818:

A Red Stick warrior fires during the annual Scott 1817 Seminole War Battle reenactment at Chattahoochee, Florida.

The following morning, just before day the party defeated the day before, supposed to have been reinforced, attacked him in his camp; but he succeeded in repulsing them with loss, notwithstanding one half of his men fled, at the first onset, and were never again brought into action. In this affair, the capt. himself received a musket ball in his side, and had one of his men dangerously wounded – this, together with the want of provisions, compelled him to return to Pensacola, bringing with him sixteen prisoners. He reports to have made seven scalps during the expedition. [IV]

The attack must have been fierce for half of the seasoned rangers to flee for their lives. Like the engagement of the previous day, this battle probably took place in what is now Washington County. The site has not been found but it was probably in the Holmes Valley region near today’s Vernon or historic Moss Hill Methodist Church.

Holmes Creek in the general area of the last battles of the First Seminole War.

Native American survivors and early white settlers of Washington County passed down these stories by mouth. One such legend holds that Holmes was also badly wounded in the fighting. Searching for a place to recover, he retreated to an island in Daniels Lake near present-day Ebro. The story has long been an important part of the folklore of the area.

Boyles took time to recover from his own wounds at Pensacola before returning to the field one last time. His final raid began in November 1818 and penetrated to the far corners of the Florida Panhandle. He even made it to the lower Pea River in Alabama: a

I have the honor to report for the information of the Major General the return of Capt. Boiles with his Rangers from his expedition to the Bays of St. Joseph, St. Andrews & St. Louis & the Rivers Pee & Choctawhatchy, bringing with him 3 scalps & about twenty prisoners. I feel no hesitation in asserting,on the authority of Capt. Boiles,that there are no hostile Indians to be found west of the Appalachiocla & below the 31st degree of Latitude. I have therefore ordered the Rangers to repair to Montgomery where they will be mustered out of service & paid forthwith. [V]

The battle that resulted in the killing of 3 warriors and capture of 20 prisoners was the last significant action of the First Seminole War. No information as to its location is found in the known reports.

Holmes Creek flows south from the Alabama line through Jackson, Holmes & Washington Counties before merging with the Choctawhatchee River.

The mention of “St. Louis” bay suggests that Boyles may have operated as far east as Apalachee Bay in the Big Bend region of Florida. Mission San Luis, now restored in Tallahassee, was in ruins by 1818 but could be accessed by water from Apalachee Bay via the St. Marks and Wakulla Rivers and Munson Slough.

The operations in West Florida by Capt. Thomas H. Boyles and his men offered a preview of the guerilla fighting and hardships that would face American troops during the Second Seminole War. Holmes and his warriors used the swamps to their advantage and only attacked when they felt sure of success. The fighting, hunger and constant movement through difficult terrain and rainy weather wore down the men of both sides. Boyles and his rangers spent the next year pleading with the government to reimburse them for horses that collapsed during the raids. Likewise exhausted, a party of Muscogee (Creek) men, women and children from the Choctawhatchee surrendered at Fort Gadsden later that year and were sent to live in the remaining portion of the Creek Nation in Alabama. Some were likely still alive to make the long walk on the Trail of Tears in 1836-1837.

The First Seminole War was over, but the conflict between the Seminoles and the United States was just beginning.

The next article will conclude this special series.

If you would like to experience the sites and sounds of the First Seminole War in person, be sure to come attend this year’s annual Scott 1817 Seminole War Battle reenactment in Chattahoochee, Florida. It will be on November 30 – December and will feature battle reenactments, living history camps, the keelboat Aux Arc, wooden boat building displays, exhibits, a mobile museum and more! Click here for more information.

To learn more about beautiful Washington County, scene of many of the events described in today’s article, please click Visit Washington County, Florida.


[I] Col. William King to Col. Robert Butler, August 11, 1818, Jackson Papers, Library of Congress.

[II] Maj. George M. Brook to Maj. Gen. Andrew Jackson, September 15, 1818, Jackson Papers, Library of Congress.

[III] Col. William King to Maj. Gen. Andrew Jackson, October 15, 1818, published in the Carolina Gazette, December 16, 1818.

[IV] Ibid.

[V] Col. William King to Col. Robert Butler, December 9, 1818, Jackson Papers, Library of Congress.





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