Assateague Island has been home to wild ponies for hundreds of years, but there are different origin stories for how they got there. The more romantic version imagines that they are descendants of the survivors of a Spanish galleon that wrecked off the coast of Assateague. There is record of a galleon, La Galga, blown off course by hurricanes in 1750. This tale is a persistent legend still believed by many.

The more likely story is that they are descendants of horses released by early settlers onto nearby Assateague to graze. Mainland farmers in the late 17th century were known to move horses to barrier islands to avoid fencing laws and taxation of livestock. However they got there, the ponies have adapted well to their wild island life.

After several disastrous fires in Chincoteague, the town recognized the need for better fire equipment. In 1925 they authorized the Chincoteague Volunteer Fire Company to hold a carnival and auction to raise funds. The event was a huge success. The revenue from the Fireman’s Carnival and other Pony Penning events enabled the fire company to modernize. As word spread, the event grew, and today attracts more than 50,000 visitors. Spectators come from all over to watch the Saltwater Cowboys swim the pony herd from Assateague to Chincoteague.