Road with Cypress and Star was completed by Vincent van Gogh in 1890, shortly after arriving in Auvers-sur-Oise. In mid-May, Vincent boarded a train alone to make his journey north from Saint-Rémy to Paris. Van Gogh spent four days with his brother's family and then took the short train trip to Auvers-sur-Oise. The small village was surrounded by wheat fields, and Vincent readily found his subject for Road with Cypress and Star in familiar motifs such as the twisting cypress trees and the stunning illumination of the broad country sky.

Nowhere is this connection to the heavens more evident than in Road with Cypress and Star, another country scene, but one that finally provides the key link to explain van Gogh’s path through life. Painted in May of 1890 as his last painting in the asylum, it presents a balanced focus, a steady combination of land and sky, allowing neither to gain dominance. We see at the bottom two people heading toward us, and behind them a horse and carriage coming in the same direction. Their backs are to the sky, ignorant to the gleaming crescent moon and solitary star behind them. They are oblivious to it, living out their daily lives while this amazing sight occurs over the mountains in the background. The moon and star are self-contained and vibrant, each one seeming to encompass a swirling new world, an unexplored portion of the journey. In the middle stands a long cypress tree, the common symbol, according to Bialostocki, of “the cemetery and death” (Welsh-Ovcharov 124), cutting the sky in two, and we recall Vincent’s comments about death as a means of travel. The tree zigzags to the top, but it somehow does not seem like it is any sort of divider. Rather, it feels more like a bridge to the sky and the heavens than anything else. In this way, we are not oblivious as the people in the painting are: we can see a link between our world and the sky. If the cypress trees, those images of death, are the bridge, then that link is obvious.