Like most of Avercamp's works, Winter Landscape with Ice Entertainment is painted in a strongly narrative way, with many anecdotes. It is teeming with detailed, evenly spread scenes. Most of the figures at work are busy sledging and skating. Skating in particular is discussed in all its qualities: tying the irons, sliding on the ice, falling and getting up, and so on. Ice hockey is played, with a few busy talking dignitaries watching. In the meantime, however, everyday life continues as usual: in the foreground a man is carrying a bundle of freshly cut reed. On the left, someone is carrying two heavy buckets. A dog eats crows on a carcass of a horse frozen to death (at the bottom left, there was another dog, wiped out, with a very faint bit of the head visible). In front of the inn, which bears the Antwerp coat of arms, is a hole in the ice from which water is scooped with a handle. A haystack behind it serves as a love nest. At the back right a few men try to get a boat out of the ice. And so it goes on. Typically, the painting also includes various naughty details. We see a couple making love, a male peeing and in a tilted boat someone is doing a big errand, their bare buttocks sticking back. This humorous approach in particular made Avercamp's work extremely popular in his time.

Avercamp's signature is on the right of a door: "HAenricus Av".