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During the Pony Swim, the Chincoteague Ponies will cross the Assateague Channel, led by the Saltwater Cowboys, just south of Veteran's Memoria…

Before houses, shops and attractions lined Main Street on Chincoteague Island, there once stood an ice cream shop, a hotel, a post office and a factory. Just over 100 years ago, the island was filled with dirt roads and wood and brick buildings, according to assistant director of the Museum of Chincoteague Island Cindy Faith. “It looks sort of like any movie set that you would have seen out west depicting the turn of the century,” Faith said. 

Before houses, shops and attractions lined Main Street on Chincoteague Island, there once stood an ice cream shop, a hotel, a post office and a factory. Just over 100 years ago, the island was filled with dirt roads and wood and brick buildings, according to assistant director of the Museum of Chincoteague Island Cindy Faith. “It looks sort of like any movie set that you would have seen out west depicting the turn of the century,” Faith said.