Typical of Albert Pinkham Ryder’s paintings, Gay Head is of a specific location—in this case the westernmost tip of Martha’s Vineyard. At one point, the land was part of a Native American reservation and had remained primarily untouched. The soft rolling hills and sweeping views of the Atlantic Ocean would have been an artist’s dream, and were typical of Ryder landscapes; however, unlike other artists who painted the majestic cliff of Gay Head, Ryder painted the view across Menemsha Bight to Prospect Hill, and featured Gay Head as the soft, grassy knoll in the foreground.
Ryder’s landscapes tended to be a combination of actual place and personal memory. Ryder would have often spent time on Martha’s Vineyard, as he lived across the bay in New Bedford and his paintings were images tainted with personal emotion; indeed, Ryder had a superb capability of conveying sentimentality in his paintings. The painting’s small size and delicate brushwork further show Ryder’s emotional connection with the landscape, as if he is looking across the water, yearning for his home.