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Chebeague Island is an island located in Casco Bay, Maine, 10 miles from Portland. These islands are sometimes referred to as "The Calendar Islands" because it was originally believed that there are about 365 islands; current estimates range from 220 to 300. Great Chebeague will be part of the town of Cumberland until July 1, 2007, when it will be become the town of Chebeague Island. As of the 2000 census, the island had a year-round population of 356. The population increases to around 2,000 in the summer months.

In 2002 Chebeague Island explored secession from Cumberland, with whom they have been tied for 184 years. The initiative gained traction after school district 51 considered closing the island elementary school. On April 5, 2006, the island won independence from Cumberland after winning votes in the Maine Senate (31-3) and House of Representatives (131-1). The town of Chebeague Island will incorporate on July 1, 2007.

Two ferry services provide transportation to the island. The Chebeague Transportation Company (CTC) makes the 15 minute run from Cousins Island, connected by bridge to Yarmouth. Casco Bay Lines also provides service on all mail-boat and other "down-bay" trips that travel beyond Long Island.

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