Bailey Island History

Bailey Island, originally called Newaggin, was first settled by Will Black, a trader from Kittery in the 1600's. The island was later claimed by Deacon Timothy Bailey of Hanover Ma., who bought the island for 1 lb. of tobacco and 1 gallon of rum. He named the island for himself.

The islands surrounding Bailey Island are rich in tales of pirate treasure and adventure. Gold was supposedly found on Elm Island, Cedar Ledge and Pond Island. Pond Island is also the site of the ghost tale telling of a murdered pirate who stands guard over a buried treasure.

The Bailey Island Motel
The Bailey Island Motel began as a five unit motel in 1958. Since that time, many changes have been made making it what it is today; an eleven unit motel and owner's residence.