Immokalee Cattle Drive and Jamboree

Before paved roads and modern development, Florida’s landscape was shaped by cowboys, cattle drives, and pioneering families who built their lives on the edge of the Big Cypress Swamp. On March 28, guests had the chance to step into that history at the annual Immokalee Cattle Drive and Jamboree. 

Hosted at Immokalee Pioneer Museum at Roberts Ranch, the free event drew families from across Southwest Florida for a full day of storytelling, music, demonstrations, and hands-on activities rooted in the region’s ranching traditions. By mid-morning, crowds lined Main Street in anticipation of the highlight of the day: hundreds of cattle walking the normally car-packed streets. 

Cows, bulls, and horses moved steadily through the heart of Immokalee, guided by local riders and led by cattle boss Heather Cleckler, a descendant of the pioneering Roberts family. In 1914, the Roberts family traveled 100 miles by oxcart over the relentless and ancient Florida terrain to trailblaze their dream of a cattle spread in Immokalee. Today, the streets are unrecognizable, but the spirit is the same.  

The cattle drive concluded at Roberts Ranch, where the celebration continued across the 13-acre historic site. Once home to cattleman Robert Roberts and his family, the preserved homestead offers a rare glimpse into daily life in early 20th-century Southwest Florida. With fifteen original buildings and exhibits, the site tells the story of families who worked the land, raised cattle, and helped shape the region. 

Although the cattle drive reached its conclusion, the celebration didn’t stop as the ranch transformed into a lively festival grounds. Visitors moved between live music performances by the Moonstone Riders Band and The Lost Rodeo Band, cattlemen’s storytelling sessions led by Dallas Townsend and Gene McAvoy, and cultural performances including folkloric Mexican dance.  

Organized by Collier County Museums with support from community partners, the Immokalee Cattle Drive and Jamboree reflects a broader effort to preserve local history while making it accessible to new generations. Events like the Cattle Drive and Jamboree do more than recreate the past; they keep it alive, reminding the community that even as Southwest Florida continues to grow, its roots remain firmly tied to the land, the cattle, and the families who built it.