Harpswell Historical Society

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The Harpswell Historical Society is dedicated to the discovery, identification, collection, preservation, interpretation, and dissemination of materials relating to the history of Harpswell and its people.

Pictures from the 2002 Calendar: Harpswell - Remember When

The Cribstone Bridge, which spans Will's Gut between Orr's and Bailey Island, was open to traffic in September 1928. The 12 foot slabs pictured here are from Pownal and Yarmouth, Me. Gravity is the mortar.

Antoine Fide's Shooting Gallery located where the present Orr's Island Post Office now stands.

The Ocean View Hotel looked out of Mackerel Cove and to Abner's Point. The road is Rt. 24. The Ocean View Hotel is no longer standing. Early 1900's.

Jennie Prince's Ice Cream Parlor, located at the bottom right of Steamboat Road, Orr's Island, Maine. circa 1915

This view is taken from Tip Top at the Southern end of Bailey Island, looking out the mouth of Mackerel Cove and across to Abner's Point.

Orr's Island, looking north with West Harpswell on the left. The road is Rt. 24

The bridge connecting Orr's and Great Island was privately built between 1833 and 18 45. In 1852, the bridge was given to the town of Harpswell. The bridge was destroyed in 1857 and rebuilt by the town.

In 1862, the novel, The Pearl of Orr's Island, by Harriet Beecher Stowe, was published. In this photo, the Pearl House is in the bottom left corner with the southern end of Orr's Island at the top

Land's End Gift Shop on Bailey Island in 1945 at the end of World War II

Prince's Point at the southern end of Orr's Island, Me.

A great day's catch for the contestants in a week long tournament, held at Mackerel Cove, Bailey Island. circa 1940's

The Yale Shop on Bailey Island. This shop is also fondly remembered as Olive Mathieson's store. She had a tea room and a soda fountain in the north end and a grocery story at the south end. The road behind is Rt. 24, the steamboat wharf is in front.