Trail rides and wagon trains, probably the oldest, most authentic form of transportation across the Old West. Pioneers moved west to fulfill dreams. Cowboys drove cattle to major markets. These are the reasons so many kids grow up with dreams of one day becoming a cowboy, or at least taking part in an old fashioned trail ride.
More than 3,000 riders hit the trail on horseback and in wagons in February to ride to the San Antonio Stock Show and Rodeo. Riders from 11 locations in South and Central Texas covered a total of 1300 miles between them, with an average of 18.9 miles per day. The trail rides all concluded in San Antonio in grand fashion inside the Frost Bank Center Rodeo Arena.
2026 Trail Bosses
- Texas Trail Ride Est. 1954 - Trail Boss David Leist, 361-550-0608
- South Texas Trail Ride Est. 1959 - Trail Boss Travis Culpepper, 361-343-6932
- Old Chisholm Trail Drivers Ride Est. 1961 - Trail Boss Judy McDougal, 210-249-1338
- Alamo Trail Ride Est. 1962 - Trail Boss Randall Hoover, 210-844-5283
- Laredo Trail Ride Est. 1962 - Trail Boss Jerry Chessher, Jr., 210-505-6868
- Hill Country Trail Ride Est. 1965 - Trail Boss Becki Kosub, 830-385-9989
- Cowboy Capital Trail Ride Est. 1969 - Trail Boss Oscar Olivarez, 210-732-6241
- Mesquite Trail Drivers Ride Est. 1965 - Trail Boss Craig Coleman, 210-422-9699
- Alamo Kountry Kickers Trail Ride Est. 1975 - Trail Boss David Weidenfeld, 830-620-8372
- GRA-Trails Trail Ride Est. 1983 - Trail Boss Justyn Gray, 325-370-2780
- La Grande International Trail Ride Est. 2020 - Trail Boss Luis Martinez, 210-878-9436