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About The Lookout

Ariel View of Flye Point

Welcome to our secluded home...

Brooklin's best kept secret is the beautiful, untouched Flye Point! Plenty of room for exploration, events or simply getting away from the fast paced world of today.

The Ocean's View

Our gazebo near the water's edge.

A beautiful spot for special events! Ideal for weddings, family reunions and adventure getaways. Feel free to bring along your kayak, bike or a long overdue great read!

Serenity on Maine's Shoreline.

A beach worth strolling.

Explore nature! Many of Maine's shoreline treasures can be found here. Let yourself escape with the therapudic sound of the ocean, wild life and peaceful surroundings.

The Lookout Inn ~ Family Established ... Family Owned

The Lookout has been owned and operated by the descendants of the Flye family for over 120 years. The name "The Lookout" came about as early as 1760 when the Flye family had to post a sentry on the hill overlooking Blue Hill Bay to watch for unfriendly "Indians" coming from the north. Established by Owen Flye in 1896, this Bed and Breakfast Inn was continued by his daughter Lettie (Flye) Smith, and then handed down to her grandson, current owner Robert "Butch" Smith, in 1974.

Over the years, expansions have been made to the Inn. Currently we have 9 rooms to rent seasonally. Almost all rooms have breath taking ocean views. Each are unique in their own historic way.

A little about the staff...

The Lookout prides itself on a warm, welcoming staff. Making you feel at home is our top priority! Our top team members are below. Feel free to reach out if you have any questions or concerns. We are here to make your experience a wonderful memory!

Robert "Butch" Smith

After serving in the military, Butch returned to Flye Point to help his grandmother Lettie. His knowledge of electical and plumbing, love for cooking and maintenance skills have been essential to owning The Lookout. His creations can be found on our evening menu and throughout our personalized catering.

Marsha Hallett-McGaha

With over 20 years experience here at The Lookout, Marsha manages many of the day to day operations. Her love for wedding and event planning adds true personalization to every occasion. When not in the office, you can often find her gardening or helping with maintenance.