By Don Holly
The article was originally posted in The Foodscape Collective’s (https://thefoodscapescollective.com/)..
Hidden away in the evergreen East Texas pine trees of Tennessee Colony, Texas (Anderson County), the Holly Farm has been a part of my family for over 100 years, spanning 5 generations. Our family farm has long been more than just a place to raise livestock and grow crops; it’s been a living testament to our heritage. Every year, when the spring rain showers roll in and the cold chill rolls out, our family hosts one of our most cherished traditions: The Holly Farm Trail Ride.
What began decades ago as a ride among friends and family has grown into a full weekend celebration of culture, community, and legacy. We’ve changed locations and even names since I was a kid, but at the center of it was my dad (Donald Holly) and my aunt Carol, who has kept this ship afloat. The trail ride brings together our local, mostly Black community of riders, young and old, who saddle up and ride the land in the spirit of the Black cowboys who helped shape the American West.
Our family’s connection to the land runs deep. What started as a way for my great-great-grandparents to provide for their family on land they risked their lives and limbs for has become something they couldn’t have imagined generations later. As fifth-generation farmers, we’ve weathered the trials and tribulations of being Black farmers in America. Horses and horsemanship have always been part of our family’s identity, which we’ve been able to hold on to in the modern era. Our annual trail ride honors that forgotten legacy and brings it vividly to life with each hoofbeat across the pasture.
The trail ride weekend is more than just a horseback journey—it’s a full-on celebration. Attendees start arriving early Friday afternoon, hauling their horses and ATVs in from across Texas and neighboring states. The fields near our home transform into a vibrant, makeshift campground, with tents, trailers, barbecue pits, and pickup trucks forming a maze of people from families to the occasional riding club or posse.
Friday night kicks off with music, local blues, Zydeco, and country bands, to your favorite line dances and radio hits, as people take to the makeshift dancefloor, and the crowd dances under lights.
Saturday is typically the heart of the event. This is when the majority of folks arrive to show off their classic cars, nice outfits, and even have mini reunions while we wait for the festivities to start. Then, with saddles cinched tight and hats tipped to the sky, the caravan (often led by my brother Jordan) sets off down a trail through our property, into the piney woods, and along old dirt roads that echo the journeys of cowboys’ past.
Some ride quarter horses, others atop gaited Tennessee Walkers or, our favorite, Standardbreds. Oftentimes, you can see wagons, decorated with family banners and flags, roll in line, pulled by mules, and children riding ponies wave to folks who gather roadside to watch. There’s laughter, storytelling (more like tall tales), and plenty of good-natured competition about whose horse looks the best or whose horse would win a hypothetical race. Seeing a young Black boy or girl climb into a saddle and ride proudly alongside their parents and grandparents is one of the most powerful sights of the weekend. It’s proof that the legacy is alive and riding strong.
Over the years, trail riding has grown into something much larger and more mainstream, especially in urban/peri-urban spaces. It’s now a regional tradition, drawing riders, musicians, vendors, and supporters from all walks of life. But we’ve kept the Holly Farm Trail Ride rooted in the values that started it all—respect for the land, love for our animals, honor for our ancestors, and commitment to community. As times change and rural traditions face new challenges with modern urbanism, we remain committed to keeping our trail ride alive. It’s not just a yearly party; it’s a cultural touchstone. It reminds us of where we come from, who we are, and the stories that deserve to be told.
When the dust settles, and the riders head home on Sunday afternoon, we always take a quiet moment to look over the land—hoofprints in the dirt, campfire ashes still smoldering, and the echoes of laughter drifting on the breeze. It’s a reminder that this place, this tradition, and this legacy still matter. From our family farm to the wider world, the Holly Farm Trail Ride is our way of saying: we were here, we still ride, and we’re not going anywhere.
