Hipster Vermont

What started as a hike has grown into a tradition built around mobility, health, wellness, family, close friends, and the kind of social connection that only happens when people share a trail, a story, and a purpose. Hipster Vermont is about staying active, enjoying the outdoors, and celebrating the people who make life better.

At the heart of the brand is the phrase “Have a Happy” — a saying made meaningful by Footie, the oldest participant, now in his 90th year. More than 45 years ago, when Footie chose a sober lifestyle, he coined the phrase as a reminder to live with gratitude, joy, and intention. Today, that same spirit carries forward through Hipster Vermont: move well, live well, and have a happy.

Each year, the Hipster Annual Hike is held on the first Saturday in August, bringing together family and friends in the Green Mountain State to honor wellness, friendship, and the shared tradition of taking the next step together.

Hipster Vermont is more than an annual hike. It is a Vermont-born lifestyle rooted in movement, wellness, connection, and legacy.

Northeast Kingdom born. Family driven. Happy by nature.