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"Vladimirka" was a common name for the Vladimir Highway, notorious for being the road where prisoners were transported to Siberia on foot. Prisoners were being transported by train by the time the painting was created at the end of the 19th century.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. Vladimirka has an immense depth of field, drawing the viewer's attention all the way to the horizon. The length of the road is highlighted by the narrow paths that run alongside it on either side. Two other paths also cross the street from left to right. There is a golubets on the right where a praying woman is standing with her knapsack on her shoulders. 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 only signs of hope are the bright spot in the horizon and the distant white church.Vladimirka is rendered with broad brushstrokes in grey-blue and ash tones. The muted colours used to depict a grey, gloomy day determine the colour tonality of the landscape. 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. Levitan accomplishes this by blending various colours together and making delicate transitions between tones. Vladimirka, together with By the Pool (1892) and Over Eternal Peace (1894), is sometimes referred to as Levitan's "gloomy trilogy".
By the Pool Vladimir Highway left Vladimir Siberia Over Eternal Peace