The Road that Lives in the Imagination

There are roads that simply take you somewhere, and then there are roads that make you wonder.  Snake Road, just outside Lake Geneva, Wisconsin, is the latter.  It winds through a quiet landscape of mature trees, old stone walls, wooden fences, and long driveways that disappear from view almost as soon as you notice them. Behind the gates and beyond the bends are gracious country homes, hidden gardens, horse pastures, and pieces of local history held closely by the land.

You rarely see the whole picture at once.  Instead, Snake Road offers small glimpses: the corner of a beautiful house through the trees, a weathered gatepost, the curve of a fence, or a narrow lane leading somewhere you can only imagine. Even the road itself seems to encourage you to slow down and pay closer attention.

Lake Geneva has long been known for its remarkable homes. After the Great Chicago Fire of 1871, prominent Chicago families began building summer estates around Geneva Lake. Over time, the area became known as the “Newport of the West”—a place where architecture, landscape, and country life came together in an especially memorable way.

But what draws us to Snake Road isn’t grandeur alone.  It’s the quiet mystery of it.

It’s the feeling of passing a place you may never enter, yet somehow remembering it. It’s imagining the rooms beyond the windows, the horses behind the fences, and the generations of people who have traveled the same shaded curves.

For me, Snake Road also brings back the particular wonder of seeing the world from a car window as a child—when an old house, a long driveway, or a horse standing beneath a tree could inspire an entire imagined life.  Perhaps that is why the road feels so connected to Westerly Road.

Westerly began with that same sense of possibility: the belief that the things surrounding us can help shape the life we imagine. A worn leather bag, an equestrian detail, a beautiful old serving piece, or a shirt with just the right drape can awaken a memory or suggest a story of its own.  The pieces we choose need not come from grand estates. What matters is that they make us pause—that they feel personal, warm, and worth carrying forward.

Snake Road reminds us that beauty does not always announce itself. Sometimes it waits behind a stand of trees. Sometimes it appears for only a moment around a bend.  And sometimes, a passing glimpse is enough to stay with us for years.