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Rewatch every moment of the 2025 Pony Swim as the Saltwater Cowboys lead the ponies across the water in Chincoteague. Available exclusively to DSN+ subscribers.

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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.