The High Pasture sums up Weir's mature approach to landscape painting, in which he used bold pictorial effects to capture both a visual impression and his intense feelings before nature. It shows his farm near Branchville, Connecticut, where he summered regularly after 1883. Like Monet's beloved Giverny, Weir's farm was an enduring source of inspiration. Writing in a 1922 essay on Weir, Duncan Phillips noticed how he "could suddenly become absorbed and fascinated by the momentary effect of a long familiar and unremarkable scene. I am thinking of what Weir found so paintable in the mere corner of a high pasture, just a bit of sunshine playing along a stone wall and over a well-worn foot path, and a silvery, green tree outspread against a warm blue sky. The design of the picture I discovered later to be original and delightful, but my first pleasure was that of recognition."
By the late nineties, Weir had changed his approach. In place of muted color and hazy, atmospheric effects, he substituted intense hues, active brushwork, and bold patterns in the manner of Twachtman. The new expressiveness of Weir's landscapes also suggested the post-impressionist influence of Ryder, who was a frequent visitor to the farm. The High Pasture can thus be seen as both a souvenir of companionable painting sessions in the Connecticut countryside and an example of Weir's new approach to landscape painting in which he moved beyond impressionism to the bolder design elements of post-impressionism.