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.

A "spindle" is a fixed marker to indicate a hazard to navigation (such as a rock which couldn't be seen at high tide). It serves the same purpose as a channel buoy, a "light beacon," or a “monument,” to warn vessels away from dangerous places or stretches of coastline. Spindles are usually iron rods with some sort of geometric object (round, flat, or triangular) on top, brightly painted (usually red) for visibility. Monuments, like the ones you see in Lane’s depictions of Half Way Rock or Norman’s Woe Reef, were made of stone and look like stumpy obelisks—or grave monuments. They were also essential as reference points for the early coastal surveys in their efforts to make more accurate charts.

 In Castine, the notable square monument in the center of the harbor marked Hosmer's Ledge.

According to the drawing Norman's Woe, 1861 (inv. 114) Lane made a painting for Florence Foster, most likely The Western Shore with Norman's Woe, 1862 (inv. 18). Foster was a long-time school teacher in Gloucester, having been born there in 1839, a daughter of Captain Thomas Jefferson Foster and Elizabeth Elwell Foster. Her great-grandfather was Colonel Joseph Foster, one of Gloucester's legendary Revolutionary War heroes.

Miss Foster's interest in culture, her ties to Gloucester and its rich history, and her situation as a teacher, made her an obvious patron of Fitz Henry Lane. She was friends with Isabel Babson Lane, who gave The Western Shore with Norman's Woe, 1862 (inv. 18) to the Cape Ann Historical Society, and the reason it is thought to be the one originally made for Foster. Foster's sister was married to Joseph Hooper, who accompanied Lane to Maine on his visits there, and her cousin was Caroline Stevens.

Florence was among the group of young, middle class New Englanders who came of age in the mid-nineteenth century, just as educational and employment opportunities for women were opening up. After completing her primary education in Gloucester, she attended Oread Institute, a women's college in Worcester, Massachusetts, and in 1860, at the age of twenty one, began working in the Gloucester schools. By 1866, she was principal of the girls' high school. Florence's obituary noted she was "a woman of ripe culture and pleasant manners, her well stored mind making her an entertaining companion, and her kindly nature making her friendship a valued treasure."

She died in 1892 without heirs.

According to the inscription on Norman's Woe, 1861 (inv. 114), a painting was made for Benjamin H. Smith after the drawing. Benjamin H. Smith (1834-1880) practiced law in Gloucester. He was born in Rockport, Massachusetts, and studied law at Yale University, graduating in 1858.

Benjamin Smith was very active in local civic affairs, and in 1863 and 1864 represented Gloucester in the General Court. He delivered the dedication speeches for both of Gloucester's Town Halls (1867 and 1871). He also served as a director of the Gloucester Lyceum and as a trustee of Gloucester's public library fund.

In 1860, Benjamin Smith married Harriet Sayward of East Gloucester. Their wedding took place in the Gloucester Universalist Church under the direction of the Reverend W. R. G. Mellen. Harriet died in 1874 and Benjamin six years later at the age of forty-seven (November 23, 1880). They left behind two young daughters.

–Martha Oaks