Norman’s Woe is a large rock sitting a few hundred feet off the western shore of Gloucester harbor. It lies between Gloucester and Magnolia and is just outside the confines of the harbor, if Eastern Point is used as the defining southern extent of the protected water. It can be reached from the shore at low tide over the rocks and is an island at high tide.

Tradition has it that a man named Norman was shipwrecked and lost there, but there is no historical record to substantiate it. Henry Wadsworth Longfellow memorialized it in his famous poem "The Wreck of the Hesperus" in 1840 though he never laid eyes on the rock until many years after he wrecked the Hesperus on it. His inspiration may have come from the wreck of the ship "Favorite" from Wiscasset, Maine on Norman’s Woe during the great blizzard of 1839. All hands were lost, one of whom was a woman who was found dead still tied to the mast which had floated ashore.

Because it lies outside the protection of the easterly arm of Eastern Point, Norman’s Woe and the surrounding rocky coast take the brunt of huge waves rolling in from the open ocean to the east, particularly after a storm. The high hills behind that western shore act as a wind block while tide and waves push a craft shoreward making Norman’s Woe the site of numerous shipwrecks and much loss of life through the years.

Lane did a drawing and some number of paintings of the site. He drew the rock from the shore looking to the south. Instead of the violent seas for which that shore is known he depicted it in a glassy calm. One of his landmark late paintings The Western Shore with Norman's Woe, 1862 (inv. 18) shows a boat drifting idly in the still late afternoon light in the cove just to the north of the rock of Norman’s Woe.