It’s time to take another peek at what is perhaps Brooklin’s most historic structure – this time without snow. Here you see the seaside facade of “The Lookout” basking in yesterday morning’s sun:
The original parts of this structure have sheltered people since about 1760. It sits on a promontory at the end of the Flye Point peninsular, where there is a panoramic view of local bays and the Atlantic Ocean. It’s a perfect spot for an observation point, which it has been from its beginning, hence its name.
At first, The Lookout was an observation point for British colonists watching primarily for unfriendly Native Americans in canoes. Later, it may have been used by rebelling American colonists watching primarily for unfriendly British in ships. Now, it’s used by summer tourists watching primarily for small sailboats, large windjammers, lobster boats and sunsets, perhaps while sipping some giggle enhancers in that screened porch dining room. Here’s one of its rooms with a view:
Leighton Archive image
Throughout all this time, The Lookout has been in the hands of one or more members of the Flye family. The present proprietor, Butch Smith, is the grandson of Lettie Beryl (Flye) Smith. The original house was expanded upward in the late 1800s into an Inn by Butch’s great uncle, Owen Flye, and has remained one since then.
The Lookout has a fine restaurant that’s open to the public in the summer, and its extensive sea vista grounds are popular for weddings and other outdoor events. (Images taken in Brooklin, Maine, on March 18, 2026, except as noted.)