Ditch The Classic

A road unlike any other in Wisconsin, the Winding Road of Highway 42 has captivated travelers for generations with its serpentine path through the northernmost reaches of Door County. Though it may look like a natural formation, its design was carefully planned in the early 20th century by renowned landscape architect Jens Jensen. Known for his philosophy of blending human-made structures seamlessly into the surrounding environment, Jensen believed that roads should mimic the natural flow of the landscape rather than cut through it in rigid, straight lines. His vision for Highway 42 was not just about transportation but about creating an experience—one that would force travelers to slow down, take in their surroundings, and appreciate the beauty of the peninsula’s forests.

At the time of its construction, Door County was still developing as a major tourist destination, and the road to Northport was an essential link for those traveling to and from Washington Island. The route was designed not for efficiency but for aesthetics, embracing the natural undulations of the landscape rather than working against them. While much of the highway leading up to this point follows a relatively straightforward path, the final stretch before the ferry landing transforms into a dramatic series of sharp curves, an unmistakable signature of Jensen’s work.

Over the decades, the Winding Road has become more than just a means of travel—it has become a symbol of Door County itself. Appearing in countless postcards, travel brochures, and photography collections, it has earned its reputation as the most photographed road in the state. It has remained largely unchanged since its creation, a rare example of a road that prioritizes beauty over speed.

Today, the Winding Road continues to delight drivers, cyclists, and photographers alike, drawing visitors eager to experience its gentle curves firsthand. Though it spans only a short distance, it has become an essential part of the journey northward, a final stretch of road that offers one last moment of enchantment before travelers depart for Washington Island or turn back to explore more of the peninsula. From above, this familiar landmark takes on a new perspective, its flowing design even more striking against the vibrant seasonal changes of the Door County landscape. Whether seen from the sky or from the driver’s seat, the Winding Road remains one of the county’s most treasured and recognizable landmarks.

All prints are of museum quality and printed in The USA. Canvas Prints are wrapped around a hardwood frame to prevent long-term wrapping and utilize a 0.75" thick wrap. Metal Prints are glossy, vibrant, and of course are ready to hang.  These prints make a statement and bring Door County home to your wall.