1649             Earliest recorded purchase from Native Americans by John Richards from Robinhood

1664             Wiscasset, including Jeremysquam island, is purchased from Native Americans by George Davie, confirmed by Robinhood.

1668             Due to “Indian Wars,” all settlements are abandoned

1734              Wiscasset Proprietors purchases Davie’s claims for his heirs. After lengthy litigation with the Kennebec Proprietors, property was sold to the permanent settlers

1751              Newly created survey map shows three settlers: Dennis Linnekin and Joseph Whittum

1760             County of Lincoln formed, named after the birthplace of the governor of Massachusetts, Thomas Pownell

1774              Jeremysquam joins with Freetown to become town of Edgecomb

1784             Vote to have a church (Meeting House) on Jeremysquam

1795              Free Will Baptist Meeting House built

1812–14        Fort McDonough earth works erected on Squaw Heights

1820             State of Maine separates from Massachusetts

1828             The island separates from Edgecomb and becomes the Town of Westport

1829             Post office established; until 1907 mail is carried by boat and wagon

1847             Wooden bridge constructed from Harrison’s on West Shore Rd. to Woolwich; destroyed by ice in 1893

1864             Methodists establish their own church next door to original Meeting House (current Westport Community Church)

1870             Westport population peaks at 798

1874             North Chapel dedicated

1877              First Steamboat lands at Westport

1885             Meeting House becomes the Town Hall

1899             Ferry to Wiscasset is established

1905             Rural Free Delivery (mail delivery) begins

1948             Electricity arrives on Westport

1950             Causeway is built across the Back River at Cowseagan Narrows

1954             Current SR 144 designated

1955             Volunteer Fire Department established

1958             Fire Department building erected

1962             Last remaining school on Westport closes

1972              Clough Point Preserve opens

1972              New high-level bridge over Cowseagan Narrows opens

2002             Heirs donate Bonyun Preserve to the Kennebec Estuary Land Trust

2002             The town name of Westport officially becomes Westport Island

2004             Wright property at the old ferry landing becomes a public boat launch and town recreation space known as Wright Landing

2017              Segerstrom Preserve at Squam Creek opens

2020             Westport Island History Center makes its home in the Wright Landing house