Bailey's Bay is a long shallow indentation in the northeastern shore of the main island of Bermuda. It stretches for about 1,500 metres (1,600 yd) along the north coast of Hamilton Parish. The settlement which stretches along the bay's coast is also called Bailey's Bay.

The entrance to the bay is protected by a long reef which rises to the surface at several points, most notably as Bay Island.

A footbridge crosses the northeastern extremity of the bay. This bridge is part of the Bermuda Railway Trail, a walking path which follows the track of the former Bermuda Railway.

The origin of the name "Bayley Bay" is a mystery. There are suggestions that it is named after the Bailey family, who settled in Bermuda after 1617. It may have been named after Captain John Bailey in 1623. However, the exact origin is unknown.

The spelling of the name also changed. So, in 1626, the bay is mentioned as "Bayley Bay" on John Speed's map. On a map dated 1783 Captain Andrew Dunford named it "Baileys Bay".^[1]