The Winfree family legacy will be celebrated as part of the ‘Cow Bayou Cattle Drive’ to be held Satuday, Sept. 17. Similar to a “ducky derby,” 500 floating toy cows will be tossed from the SH-105 bridge crossing Cow Bayou in Orangefield and be herded by boat and cowboys on jet skis over a mile away to Cow Bayou Marina in Bridge City.

Port of Orange board member, Barbara Winfree, wife of the late Lester “Buckshot” Winfree, will start the ‘cattle drive’ at high-noon by dropping the herd from the Orangefield bridge. She will journey with the drive down the bayou by boat to pluck the winning cow from the water as it crosses the finish line.

The grand prize winner will receive a 40-inch television donated by the Sears Hometown Store in Orange. Prizes will be awarded for the first five places during the Bridge City Heritage Festival on Oct. 1.

“We are delighted to recognize the Winfree family. They have played such a large role in our local history,” said Paige Williams, chairwoman of the event. “It’s going to fun. There are still cows available for anyone who wants to enter.”

The Cow Bayou Cattle Drive will begin near what was once Winfree’s Crossing, an outpost for cattlemen driving herds to New Orleans. Abraham Winfree settled on the land in 1831 when it belonged to Mexico. He was one of the first Anglos to settle in what became Orange County. Winfree’s Crossing was along the Opelousas Trail. Cowboys driving cattle would stay there overnight, and Abraham kept a 20-acre pen for the cattle.

Family history says Republic of Texas soldiers, traveling with captured Mexican Gen. Santa Ana to New Orleans after the Battle of San Jacinto in 1836, stopped at Abraham’s and spent the night. Abraham was also friends with Claiborne West (the park’s namesake) who lived in the Cow Bayou settlement and signed the Texas Declaration of Independence.

The Winfree name is legendary in Orange County. Most notable in recent history was Lester “Buckshot” Winfree, a cattleman, rice farmer and owner of Winfree Cattle and Rice trucking company. He served as a Port of Orange board member from the 1980’s until his death in 2010. Barbara Winfree was unanimously approved to fill her husband’s seat on the board.

Barbara grew up in Bloomington, Texas, and graduated from Lamar University in 1981. She taught kindergarten at Orangefield Elementary School for 22 years and retired about 10 years ago. Barbara met Buckshot at a rodeo in Robstown, Texas. They were married 46 years. Their children are Kirk Dillard, Will Winfree, Leslie Holtkamp and Elizabeth Neely.

The Cow Bayou Cattle Drive is being hosted by the Historical Museum of Bridge City, a 501 (c) (3) nonprofit charitable organization formed in 2009 to preserve local history and enhance tourism. Sponsoring the event is SET Vending LLC.

Those interested in purchasing entries to compete in the cattle drive can contact Paige Williams at 409-670-3192 or e-mail at The Bridge City Heritage Festival and the Historical Museum of Bridge City can both be found on Facebook.