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Diamond Island Pass: a Channel in Cumberland County, Maine. Many of the islands are small lobster fishing communities, the most populated of which are: Peaks Island, Long Island, Great Diamond Island, and Chebeague Island. The major islands in the bay are served by the Casco Bay Lines ferry service in located at the Maine State Pier in Portland. The other islands see fewer ferries and no car transport, the Diamonds and Long Island are served primarily by the Diamond Pass run, which is popular with tourists in the summer months.