Father and Son Complete 120-Mile Walk Across Connecticut

A father and son from Darien documented an eight-day walk across Connecticut, walking 120 miles across the entire state.

Eleven-year-old Christopher Hilton and dad Chuck Hilton of Darien recently completed an eight-day, 120-mile walk across the state of Connecticut. The two walked the length of Boston Post Road (US Route 1) from the state line in Port Chester, NY, through 25 coastal Connecticut towns and ended up in Westerly, RI.

DarienAt the starting line: Chris learns how to buy a train ticket, read a train schedule, and catch a train (to Port Chester, NY). Chuck Hilton

In addition to burning a few calories and spending some quality time together, the primary goal of the walk was to discover and explore the many historical, natural, and cultural aspects of the state they call home.

The trip took place over eight non-consecutive days, beginning in Port Chester, NY on Aug. 10 and ending in Westerley, RI, on Sept. 29. The pair plotted their path along Route 1 and the Metro-North train line, which they rode to and from their starting and stopping points.

The inspiration for the trip came from a friend of Hilton’s who had spent a day driving Post Road from one end of the state to another. “I thought ‘What a cool idea,’” says Hilton, a founding partner at Hilton-VanderHorn, Architects in Greenwich. “I’ve spent years living in this end of the state, hopping on and off the highway to destinations in many neighboring communities, but [I] never really threaded them together in a cohesive way. Likewise, I also heard so much about the beauty of the coastal communities on the other end of the state and have had little time to discover them. Walking Post Road seemed like the perfect way to explore all of this.”

Christopher, a student at Middlesex Middle School, embraced the unusual challenge presented by his father—at first. A few hours and a couple blisters later, and the scope of what they had committed to began to sink in. But great conversations, new discoveries, and determination fueled their journey along the way.

“It was an amazing trip filled with conversations about history, economic realities, and explanations about our many surroundings,” Hilton says.  Equally important lessons on topics such as the importance of good planning and perseverance needed little conversation. What was the best part of the trip for Chris? That’s easy, he says: It was “spending so much time with my dad.”


The walk from Southport to Bridgeport, where the pair caught a Bluefish game, spurred a conversation about Bridgeport’s industrial past, changes in the local economy, and the evolution of local industries.

New Haven

On Aug. 24, father and son walked 17 miles from New Haven (beginning at Union Station, pictured here) to Guilford, followed by a 16-mile walk to Old Saybrook the next day.

Mystic Pizza
Near the end of the walk, the duo hit Mystic, where they walked through the historic downtown area, discussed the colonial architecture, and had lunch at Mystic Pizza. All photos courtesy of Chuck Hilton