The Gay Head was a sidewheel steamer operating as a ferry serving the islands of Martha's Vineyard and Nantucket during the end of the nineteenth century and the beginning of the twentieth. It was named after the town of Gay Head, Massachusetts, later renamed Aquinnah.
The Gay Head was built in 1891 in Philadelphia for the New Bedford, Martha's Vineyard, and Nantucket Steamboat Co. It was 701 tons, 203 feet long, 34 foot beam, a draft of 5ý feet, with encased paddlewheels. The engine was built by Pusey & Jones Co. in Philadelphia. It was the largest sidewheeler ever operated by the company.
According to a 1961 Vineyard Gazette article:
Gay Head was commanded initially in 1891 by Capt. A. P. Bartow and Capt. G. L. Daggett, and later by Capt. Charles H. Fishback of Nantucket, Capt. Charles H. Coulter (resigned 1909), and Capt. J. W. Merriman.
In July 1898, the Gay Head collided with the steamer Nantucket while crossing Vineyard Sound in a dense fog. The Nantuckets bow was badly damaged in the accident.
The Gay Head operated until 1924, after 33 years of operation.