Owls Head, which had been a part of South Thomaston, became a town on July 9, 1921. Included in this section were the areas of Ash Point, Ingraham's Hill, Crescent Beach, Holiday Beach, Ballyhac, and of course the section where the Owls Head lighthouse is located.

People in this Owls Head area had been concerned about problems involving the one room schools over the years. They felt that the five schools here had been neglected, and that the schools in the South Thomaston Village area (the Keag) were receiving all the benefits. So this was one reason for the separation. The dividing line between Owls Head and South Thomaston begins on the Dublin Road (off the Ash Point Road) at the bridge, with the Town's area extending completely around the shore to the Rockland City line (at Ingraham's Hill).

It is generally believed the Town derived its name from sailors who in 1759 observed the tall headland of trap rock extending far into the water in the extreme northeastern end of the town (the lighthouse area) and imagined that it bore a resemblance to the neck and head of an owl.

When Owls Head was visited by Champlain in 1605, it was called Bedabedec Point the Indian word meaning, "Cape of the Winds". Some historians claim the name is of Indian origin and is expressed in their language by the word, "Mecadacut", meaning "Owls Head".

The first town meeting following incorporation was held on August 29, 1921, at 6:30 PM at the Owls Head School house situated across from the present fire station. The meeting was called to order by Rodney E. Feyler, Justice of the Peace. During the balloting for Moderator, 192 votes were cast with C. Vey Holman elected over Charles Crowley.

Other officers elected were James A. Collins, Town Clerk; Carl Libby, 1st Selectman; Arthur C. Robbins, 2nd Selectman; Perley Fiske, 3rd Selectman; Charles Livingston, Tax Collector and Treasurer; Henry Closson road Commissioner. Elected to the school board were Mrs. Lura Whalen, Mrs. Belle Collins and Mrs. Edith Young. Harold W. Philbrook, John F. Whalen and John Garnett were appointed constables; Albert Guptill, truant officer and Arthur A. Bain, health officer. The meeting was adjourned to September 26, 1921 for action on various appropriations.

The first regular Town meeting of 1922 was held on March 20 at 10 AM at the Pavillion (part of the Crescent Beach Inn), Crescent beach, with action on 37 articles. Allan B. Borgerson served as moderator. James A. Collins was reelected as Town Clerk and Carl Libby was reelected as 1st Selectman. However, following the election of John Whalen as 2nd Selectmen and Maynard Curtis as 3rd Selectman, Carl Libby resigned at the meeting and Harold W. Philbrook was elected in his place. Mrs. Abbie Heard was chosen for the school board for three years. Also reelected were Charles Livingston, Tax Collector and Treasurer and Henry Closson, Road Commissioner. Walter L. Snowman was appointed constable.

There was always a great amount of sociability in Owls Head, with dances, parties and other activities. There were stores jointly operated along with the post offices, both at Owls Head Village and Ash Point Village. This created a lot of daily social activity as well as the passing along of information, such as deaths, weddings, the birth of a child and anything else that was newsworthy. The notices of town meetings were always posted here, followed by "discussion" groups, concerning the articles in the Town Warrant.

There were several so-called ice cream parlors where people could meet socially. One of these was in the building now housing the Post Office. Dances were also held on the second floor. Wherever there was a large extra room or a large farmhouse available, dances were apt to be held.

The beautiful light house and beach areas in Town drew many tourists who at the time arrived in Rockland by train or the Boston boat. They stayed at the several inns and boarding houses in town.

Many cottages were built along the beautiful beach areas including all of Ash Point, Crescent Beach, Hendrickson's Point, Ginn Point, and Holiday Beach. Some were also built at the Owls Head harbor area where the Owls Head Inn, formerly the Adam's House, (built by Joshua Adams) was located. The old Inn has been used as a private residence since 1941.

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