Trail Bosses: Two women to lead the way in trail ride ahead of Rodeo 2020

January 28, 2020

Trail Bosses: Two women to lead the way in trail ride ahead of Rodeo 2020

BY: Marina Olson

A common saying among those involved with the Houston Livestock Show and Rodeo™ trail rides is: All trails lead to Houston. 

Each year, more than 2,000 people participate in the 12 trail rides - but only one of them has the distinction of being led by a woman. Rosetta Gray is in charge of the Southwestern Trail Ride. Her assistant trail boss, Elizabeth Cook, is also female.

Gray has been involved with the Southwestern Trail Ride since 1981. 

“I moved here from Mississippi, met a guy who rode on a trail ride, and he invited me to go,” she said. “The first year, I rode in one of the wagons but as soon as the ride was over, I bought a horse!” 

From there, she continued working toward the goal of becoming the trail boss and leading the ride. 2019 marked Gray’s 12th ride as trail boss. Her duties first began in May 2007 and her first ride was in 2008. 

The Southwestern Trail Ride was officially chartered in 1974 when the Houston Livestock Show and Rodeo was still known as the Houston Fat Stock Show. The ride begins at the Stephen F. Austin monument in West Columbia, Texas, and spans 123 miles on the way to Houston. 

The trail riders meet the Saturday before Rodeo events kick off at NRG Park. The route leads the riders along major highways, so it is the work of the scouts and police escorts to ensure everyone’s safety while participating. There are approximately 250 riders involved in Gray's trail ride, with 10 wagons accompanying the riders on horseback. 

The wagons carry supplies including bedding, personal items and everything needed for cozy dinners around the campfire. Often overlooked, the trail boss must master the physical and mental work that goes into the successful planning and execution of the annual trail ride. 

This is exactly where Gray shines. 

While she knew right away that she wanted to get more involved, Gray did not realize at the time that she would be making history by leading the Southwestern Trail Ride. 

She said she is “thrilled to death” about her position as trail boss and now fully recognizes the significance of what she is doing. As she rose up in the ranks within the organization, she took notice of Cook, another strong female presence on the ride. 

Gray said she knew that if she had the opportunity to be in charge, Cook was someone she would want by her side. Cook, the current assistant trail boss, has been involved with the ride for 30 years in different capacities and may have the opportunity to take over as trail boss, should Gray ever choose to give up the reins. 

“Rosetta and I complement each other well as she’s very firm, and I’m not as much,” Cook said. “She rides the full trail, where I tend to make sure I’m reachable by the leadership and that each campsite that we use along the way is cleaned up and ready for the next group.” 

These women are paving the way for hopeful female trail bosses everywhere. It is certain that Gray, Cook and those they are leading will leave a lasting impression on the future of the Southwestern Trail Ride.