Bailey Island in Harpswell

Pronunciation: BAY-lee eye-land

Bailey Island lies in the town of Harpswell on Casco Bay. Its shape, exposed shoreline, fishing harbor, and bridge connection to Orrs Island have made it one of the most recognizable communities along this part of the Maine coast.

An island connected by stone

For roughly two centuries after European settlement, Bailey Island had no road connection to the mainland. A bridge was proposed as early as 1872, but a permanent crossing did not arrive until the twentieth century.

The island is linked to Orrs Island by the structure locally called the Cribstone Bridge. It crosses Will’s Gut using massive granite blocks arranged in an open crib pattern. The openings permit strong tidal currents to move through the structure rather than pressing against a continuous causeway.

The bridge was completed in 1928, replacing Bailey Island’s dependence on water transportation for its connection with the rest of Harpswell. As its granite supports shifted over time, preservation became necessary. The crossing was dismantled and reconstructed while retaining its historic form, reopening on November 20, 2010 with a renewed foundation, travel surface, and sidewalk.

Settlement and changing names

The island was known by the Abenaki name Newaggin, associated with the swift currents in the surrounding waters. William Black settled there by 1727, and an early claim referred to it as Will’s Island.

In 1750, Hanna Curtis, wife of Deacon Timothy Bailey, purchased the island from the North Yarmouth land proprietors. The transaction displaced the earlier Black family claim, and the island later took the Bailey name.

Fishing shaped the local economy from the eighteenth century onward, with lobstering becoming especially prominent. Houses and businesses developed largely along the road that runs the island’s length.

Mackerel Cove and coastal life

Mackerel Cove, at the southern end of Bailey Island, is a major fishing harbor. Working boats and pleasure craft share its waters, while floats and lobster gear reflect the continuing role of the marine economy. Lobster cars beneath some floats keep catches alive in seawater before delivery to market.

The island is densely developed, and its finite land and freshwater resources constrain additional building. Saltwater intrusion into wells is one concern associated with island living.

Wartime lookout towers

During World War II, observation towers were erected on Bailey Island and elsewhere around Casco Bay. Watchers used them to scan coastal approaches for submarines, suspicious vessels, and other activity. The surviving Bailey Island towers are inactive and not open to the public.

Landmarks and public memory

A replica of Victor B. Kahill’s sculpture commonly known as “The Maine Lobsterman,” first exhibited at the 1939 World’s Fair, stands at the island’s southern end overlooking Casco Bay and its islands.

Bailey Island Library Hall

Library Hall was erected in 1912 by the Bailey Island Library Association to serve as both a social hall and lending library. Its design references Mount Vernon through features including a cupola, colonnade, and Palladian windows. Although it no longer operates as a library, the building continues as a community hall.

Halfway Rock Light Station

Off Bailey Island in Casco Bay, Halfway Rock Light Station marks the approximate midpoint between Cape Elizabeth and Cape Small.

Explore the Harpswell islands and villages

Continue with Harpswell, Eagle Island, Haskell Island, Orrs Island, Harpswell Center, West and South Harpswell, North Harpswell, and Cundys Harbor.