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The town of Edgartown, the oldest on the island, is steeped in history as is the annual Edgartown Regatta. Each year hundreds of sailors converge on the Edgartown Harbor for the start of the races. Several classes of yachts compete in an array of competitions over the course of the weekend. The regatta takes place in mid-July. Spectators can take in the gorgeous sailboats from harborside. Free for spectators, call for registration information or visit the website.