One of the first murals painted for City Hall, this work represents the founding of Gloucester. Created under the Public Works of Art Program (PWAP) during the Civil Works Administration (CWA) in the winter of 1933-34, it predates the Works Progress Administration (WPA) of 1935. The PWAP was an experimental federal program providing public service jobs to the unemployed, and artists were hired to create works in public buildings such as schools, orphanages, libraries, museums, and city halls.

As with most of Winter’s City Hall murals, this one is allegorical and heroic, featuring strong drawing and high color. The group of people on the top right represents the earliest European settlers on Cape Ann, sent by the English Dorchester Company in 1623, three years after the settlement in Plymouth, Massachusetts. Gloucester was established as a commercial colony and investment. Winter depicts the settlers unloading supplies from their ship, with a Native American smoking a peace pipe similar to one found in an Essex archeological dig watching them. In the background, Winter pictures "Old Mother Ann," a rock formation near Bass Rocks resembling a woman's profile, looking out to sea, and "Norman's Woe," an island off the coast named for the boats that have foundered there.

In the upper left, Winter represents the first city fathers discussing plans for their new town. Winter used contemporary city officials to represent the first city fathers: Mayor George H. Newell is holding the plans while selectman Henry H. Parsons bends over them. From left to right, the others are John J. Burke, Percy W. Wheeler, John A. Stoddard, Isaac Patch, William J. MacInnis, C. Homer Barrett, and John E. Parker. Behind the city fathers, carpenters are building stages, now called wharves, which gave the name Stage Fort Park to the site of the first settlement. Gloucester was incorporated as a town in 1642 and as a city in 1873 when the current City Hall was built.

Moving down to the lower left, a woman with a spinning wheel and another with a baby (painted by Winter's wife, Alice Beach Winter, a noted painter of children) symbolize Gloucester's weaving industry and its home life. Winter portrays Gloucester's historic connection to the sea with a group of men building boats and another carrying fish and nets. The young fisherman in a sou’wester with a basket of mackerel and haddock, two fish that rebuilt Gloucester’s economy after the American Revolution, represents a so'wester, while the older fisherman pulling in nets is a gill netter.

In the center of the painting, "History," a gray-robed woman with a quill and book, records events. To her right is the Seal of Gloucester with its fish, sail, anchor, and arm and hammer, used until 1873 when it was incorporated as a city. At "History's" feet, almost coming off the canvas at the edge of the frame, is "Vision," a boy looking outward and upward into the future.

Additionally, chemists from the Russia Cement Company in Gloucester developed the special casein glue used to fasten this canvas mural to the wall.