Art historian Aleksei Fedorov-Davydov described the painting as one of Levitan's best; it was his "universally recognised masterpiece", in which "deep social content is expressed organically and directly in the landscape".

On one occasion, as they were returning from a hunt, they emerged onto the Vladimir Highway, an unpaved road that ran east from Moscow and was frequently used to ferry prisoners to Siberia for exile.

A crumbling old dovecote with a weathered icon and two distant golubets [ru] (a roof on a grave or worship cross) both hinted at long-forgotten antiquity.

[17] In a letter to Pavel Tretyakov dated 11 March 1894, Levitan wrote: "'Vladimirka' will probably return from the exhibition one of these days; take it and calm me and her [the painting]".

[20] The painting depicts a vast plain with a road that extends from the foreground into the middle, passing through woods and fields before vanishing in the horizon's blue haze.

[12] According to Averil King, the lonely figure of the woman praying to the golubets, the cloudy landscape and the desolate road all create a "picture filled with sadness and foreboding" that suggests "the despair of the shackled men and women who had trudged eastward through these lonely wastes".

The lighter colours of the white church and the yellow stripe of ripening rye near the horizon do not stand out in this colouristic scheme.

Despite using a muted palette, the painter is able to maintain the depth and variety of colour; he retains all the hues found in nature and incorporates them harmoniously into the landscape, giving it a single tone.

[31] Nesterov wrote that Vladimirka successfully combined "historical fiction with a complete, finished workmanship" and that it is "one of the most mature creations" of the artist in a letter he sent to the art historian Vladimir Kemenov on 10 October 1938.

[32] Art historian Aleksei Fedorov-Davydov stated that Vladimirka is one of Levitan's best works and his "universally recognised masterpiece" in his monograph on the artist.

Fedorov-Davydov states that Levitan portrays nature in this painting in a conventional manner while revealing the rich inner content of even the most commonplace objects through the "most simple and ordinary motive of the plain with the road going away".

[33] According to him, the road that forms the foundation of the image motif successfully draws the viewer into the complexity of the landscape and progressively reveals its inner meaning.

[34] Art historian Vladimir Petrov noted that Vladimirka is a rare instance of a polyphonic historical landscape.

Drawing a parallel with the infamous Vladimir Highway, Chukovsky questioned whether it could represent all of the great artist's creations, with his calm and reconciled awareness of the hopelessness of all Faustian impulses of the human spirit.