Charles Island is accessible from shore via a tombolo (locally referred to as a sandbar), which is exposed at low tide. According to early local histories, the Sachem Ansantawae resided there during the summer months. European discovery of the island occurred in 1614 when Adriaen Block sailed through and mapped Long Island Sound. The island appears on his hand-drawn map found in The Netherlands National Archives.
After the Milford area was settled by the English in 1639 the island was referred to as Milford Island. After Charles Deal bought the island in 1657 it became known as Charles Island. Deal made a failed attempt to raise tobacco on the island – one of the first such efforts in Connecticut.
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