Watching Brylee, Aly and Saryah pet a horse for the first time at the 2nd Annual Gateway Trail Ride and Field Party conjured up a childhood memory.
Brylee and Aly, both seven, were eager to pet the overwhelmingly friendly pony. Saryah, 5, was terrified. The more she tried to cower and duck.
“He’s just a baby,” said Jordan, the adult who brought the girls over to the stall. The horse — whose name we never knew — tried even harder than Jordan to convince Saryah that he wanted to make friends. He ducked down with her. He tried to sniff and lick her as she squirmed behind Jordan. The horse then redirected his attention toward getting a sip from Jordan’s bottle of beer.
“This beer has apple in it,” Jordan said. “He wants some because he can smell the apples. Did you know that horses love apples?”
As the youngsters had their first taste of farm life, it reminded me of when our family would make the annual summer trip to Clow, Arkansas — just across the tracks from Hope.
It’s not a unique experience for the grandchildren and children of the Great Migration. But witnessing children who likely have never experienced their family’s Southern roots — which has been the case for generations.
“Another Gateway Trail Ride is officially in the books, and once again, we proved what happens when community comes together with pure love and positive energy,” said Michael B. Whit, award-winning country singer and Gateway Trail Ride brainchild.
He owns Rolling Ranch, which sits on the border of Cahokia and Sauget just across the bridge in Illinois.
For the second year, the event — an all-day affair that started early in the afternoon and stretched into night — has given people looking to party an alternative to nightclubs. It also leans into the Black cowboy culture that has resurged in the past five years or so.
Watching the youth and the grownups have a ball kicking up dirt — whether it was dancing, racing, wrestling farm animals or watching the performances on the main stage — was a reminder of what had to be left behind when we escaped racial terror and searched for more opportunities.
Long before Hollywood rewrote the story, Black riders, ranchers and trail hands shaped the backbone of American farm life — especially in the South and Midwest. With the resurgence of Black cowboy culture in recent years, Gateway Trail Ride provided a place where Black families can reconnect with the land, the culture and each other.
“All of St. Louis North, South, West and East Saint pulled up, reconnected with their roots, and showed out,” Whit said. “We are actively changing the narrative for our hometowns every single year. Cahokia showed the world what peace, unity and genuine togetherness look like when we ride as one.”
They rode as one — and danced as one, thanks to the lineup of artists.
Cupid, the mind behind the family reunion and Black barbecue essential line dance “Cupid Shuffle,” was the headliner for year two.
Day turning into night didn’t stop guests from getting into formation. And they were already versed in his latest instructional slide anthem, “Cookout.”
“You gonna rock your body this way, kick your legs up like you Mary J,” Cupid said. The dancers were already following suit. “It’s going down at the cookout,” Cupid said. “Step two times to the right. To the left we can do this all night.”
And they did.
“I will be at every one of these,” hip-hop artist Dope Pitacrow said. “I can’t wait for next year.”
Whit and organizers saw more than a successful event.
“I love our people! No fighting, no arguments, just all love shown,” said Marius Jackson, former mayor of neighboring city Centerville, IL.
They proclaimed the Gateway Trail Ride a win for the culture. Whit expressed as much on his Facebook page.
“Meanwhile in Cahokia… history repeated itself in the best way possible,” Whit said. “Big thanks to the entire GWTR 2026 crew team for curating and pushing this event to the public, even when we had mountains to climb and rain to dodge. We did it together!”