This is one of the few winter scenes painted by Hendrick Dubbels still preserved today. In the Museum`s catalogues it is described as a scene with skaters, although only three of the many characters depicted here are actually skating, and one is putting on skates. The 1873 and 1878 editions state that, despite the signature, some consider this to be by Bonaventura Peeters; the 1885 publication mentions Bredius`s attribution to Cornelis Vroom; and from 1889 to 1907, the institution`s catalogues include it as an original by Hendrick`s son, Jan Dubbels (active 1705–1727), owing to the signature.

Valdivieso (1973) places The Port of Amsterdam in Winter in the painter`s early period, around 1640–50. However, Middendorf (1989), who locates the setting as the Eastern Dock of the Port of Amsterdam, considers it to be from 1656–60. Indeed, the bright colours appear to correspond to the painter`s second stage when, after working at Simon de Vlieger`s studio, he gave up the monochromatic range characteristic of his initial works. Moreover, the work`s compositional structure -based on a balance of horizontal and vertical planes- is classical. This and the very low level at which the line of the horizon is placed, so that the sky occupies three quarters of the composition, make it similar to the emblematic views of the Port of Amsterdam -in this case the Eastern Dock- which Hendrick Dubbels cultivated between 1654 and 1660.

The brushwork is delicate and uniform and, as is typical of these views painted by the artist, the colouring is cold, based on blues and greys, with hints of pink in the horizon. The crowd of little figures is engaged in various leisure activities and grouped together into little genre scenes, bringing the scene to life in the tradition of Hendrick Avercamp (1585-1634). Afurther two examples of this scene are known to exist: one in the Steinmeyer collection (Cologne), which Hofstede de Groot catalogues as an original by Jan de la Capelle (1626-1679) but which Valdivieso believes to be a copy of inferior quality of the Prado version; and another, known as People on the Harbour, auctioned in Barcelona as the work of Abraham Storck (ca. 1635-1710), which Valdivieso also considers a replica of the Prado original (Posada Kubissa, T.: Pintura holandesa en el Museo Nacional del Prado. Catálogo razonado, 2009, p. 302).