Here’s “The Lookout,” one of Brooklin’s most historic structures in one of the Town’s most beautiful settings overlooking Blue Hill Bay and the ocean beyond. The original, two-story 1760 Colonial style house and property were part of a land grant from the King of England to William Flye and the property has remained in the family since.
The original structure was named The Lookout in the 1760s because it served as a sentry point to detect hostile seafaring Native Americans who were, let us say, not unreasonably displeased with Europeans granting their land away. In the late 1800s, a third floor and west wing were added as part of a conversion to an inn.
Today, the whole area is called Flye Point and The Lookout property is popular for outdoor weddings and other open-air events, while the Inn portion has summer rooms with breathtaking views. The same views and fine meals are available in the summer to the public in The Lookout’s dining room.
(Images taken in Brooklin, Maine, on January18, 2026.)