Winter's mural is an allegorical painting that encapsulates his vision for city government, depicting essential duties and responsibilities. The painting is divided into two primary sections: "health" and ""planning."

In the "health" section, a nurse helps a boy while doctors and scientists confer. At the top of the painting, a figure represents the role of chemistry in medicine, with Gloucester's Addison-Gilbert Hospital in the background. The "planning""section features a vision of city planning with a bridge over the Annisquam River that did not exist in 1937. Winter imagined a three-span granite structure with lighthouse-shaped columns aiding mariners and drivers. This section also includes two architects in Renaissance costumes examining blueprints, and two children building a model of the new High School, nearly completed in 1937.

At the center of the mural, the responsibilities of municipal government are symbolized. A figure on a marble throne, holding the fasces (an ancient symbol of law), is flanked by the flags of Massachusetts and the United States, symbolizing authority. Protective spirits, or genii, hold the city seal and a lamp of enlightenment. The mural represents various municipal responsibilities, depicted through figures of city planners, firefighters, police officers, city council members, nurses, and teachers. These figures, wholesome and open-faced, embody the trust and duties of public service. Local community figures posed for the scene, enhancing its connection to the city.