Sauget’s Rolling Ranch came alive for the inaugural Gateway Trail Ride & Field Party, a three-day celebration that blended family fun, live music, and deep cultural roots. Hosted by Michael B. Whit, the Certified Steppas Trail Riders, and promoter Phil of Liquid Assets, the event spotlighted the often-overlooked legacy of Black cowboy culture.

Families enjoyed pony rides, sack races, mechanical bulls, and even a spirited line dance showdown with $1,000 in cash prizes. The nights pulsed with energy as Whit, Pokey Bear, and local DJs brought a mix of country, R&B, funk, and hip hop to the stage.

But beyond the games and the music, the weekend carried a powerful message: cowboy culture has always been part of Black history.

“Regardless of what the mainstream country music scene refuses to accept or believe, cowboy culture is Black culture. It has been from the very beginning.” – Zaria Mac

That truth feels especially relevant in 2025, as country music dominates charts with cross-genre hits like Shaboozey’s “A Bar Song (Tipsy)” – inspired by St. Louis’ own J-Kwon – and Beyoncé’s Grammy-winning Cowboy Carter. Both projects stirred conversations about authenticity, ownership, and who gets to define the culture.

The Gateway Trail Ride & Field Party flipped that conversation back to where it belongs: homegrown, community-centered, and proudly rooted in Black tradition.

Photos Courtesy of Front ‘n Center

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