When Road to Ridgefield was included in the 1889 sale of the work of Twachtman and Julian Alden Weir, held at the Fifth Avenue Art Galleries (see Exhibitions), it was noticed by a reviewer for the New York Tribune, who remarked: "Of the pictures which will be popularly called complete, the best example is the beautiful 'Road to Ridgefield,' a study of a gray and yellow road and buildings with accompaniments of green grass and foliage underneath a sky where 'the blue that comes after rain,' as the Chinese have it, shows between the lightest of white clouds. This might be called one of the more obvious landscapes, but the delicacy of its harmonious colors is by no means easily exhausted."
The painting sold from the exhibition for $70, according to an article in the New York Sun. Twachtman depicted the same site, probably Nod Hill Road in Branchville, Connecticut, where Weir's home was situated, in the pastel, ’Neath Summer Skies, (P.801), and in another oil on panel, The House in Nodd (OP.815). In this instance, his viewpoint was along the diagonal of the road, with the buildings and land establishing an opposing triangular wedge at the left. Closer to the farm buildings than in ’Neath Summer Skies, he included more details, such as the stone wall and its gate entry. A tree that appears to the right of the barn in The House in Nodd is now behind it. In Windy Day (OP.817), another painting in the 1889 sale, Twachtman's viewpoint was possibly from the opposite side of the gate, looking toward the road.