In most of the Old West, the ranchers managed two yearly round-ups. A spring round-up was done to identify and brand the new calves in a herd, and castrate any male calves that were not needed for reproduction (these cattle were called “steers” and often outnumbered the females).
It was a big job to get cattle from the open range to the railhead or directly to market. Round-ups for this purpose were usually done in the fall and could take several weeks. The cowboys might live out on the range for that entire time, accompanied by a ramrod (boss), a chuck wagon and possibly a cook. In addition to food stores, the chuck wagon carried their water and emergency medical supplies.
However long it took, a cowboy would draw his wages at the drive’s destination. Many would then find themselves unemployed until the following spring. Since the work load was so light in the winter, particularly in the northern territories, only a few favored cowboys were actually employed year-round. It’s no wonder that most cowboys were young, unmarried, and tended to drift from one town to another.