Old Post Road: Historic Fairfield Estate For Sale


In Colonial era America, the postal route between Boston and Philadelphia went straight through Fairfield, Connecticut. The original stretch of that road remaining became known as Old Post Road. It is one of three historically designated districts in the town. Lined with beautiful older homes, two churches and the original town green, Old Post Road takes the shape of an inverted capital L, with each end point converging onto the bustling main Post Road, with its public library, town gazebo, concert green, restaurants, Fairfield University bookstore and coffee shop, theatre and train station.

The Sun Tavern

The Sun Tavern still stands at the Old Post Road town green. Built in 1780, it was a popular stopping point for travelers, both ordinary and prominent. Benjamin Franklin was a frequent visitor when he was postmaster general. There’s a story about the time he arrived to find it full of people. He stood at the door and announced in a loud voice that he’d like a plate of oysters for his horse. When a few patrons got up to take a look at his horse….he quickly took an empty seat.

766 Old Post Road

766 Old Post Road was built in the same year as the Sun Tavern. This home has had transformations over the years, including one in 1929-1930 when it was redesigned by Joseph Wakeman as a classic center hall colonial with 9 foot ceilings. The present owners thoroughly and thoughtfully updated this gem of time and place. It still sits on the same spot, surrounded by 1.73 acres of its original land, now the largest single parcel remaining: a rare combination of country setting in the center of the thriving town of Fairfield, just fifty miles from Manhattan.

Fairfield is also the place where the largest Memorial Day parade in Connecticut is held. There is nothing quite like the feeling elicited by the boom of drums, brass instruments and bagpipes, along with the occasional cannon sound when experienced with a mass of marchers and spectators along the Post and Old Post roads.

Penfield Beach Reef Lighthouse

A ten minute stroll in the direction away from town will land you on a beautiful stretch of sandy beach at the Long Island Sound. As part of a huge sandbar, the sand is particularly soft. At low tide, you can place your beach chair in the warm wet sand, sit among children with shovels and pails, and the time stands still. As the town with the most public beachfront in Fairfield County, Fairfield’s two largest beaches, Jennings and Penfield, adjoin each other. Together, they offer an abundance of picnic tables, barbecue grills, snack bars, play equipment and enough elbow room to host the entire town each year for the 4th of July fireworks display. Every so often, a live band plays John Philip Sousa music for this Independence Day holiday.

Meandering back to the Old Post Road from the beach, you can cut through the town green, past the newly rebuilt Fairfield Museum and History Center, which resembles a beautiful modern barn. You can catch one of their popular exhibits, such as the toy train exhibit, held every holiday season.

Burr Mansion

Walking within the green, you can also stroll through the grounds of the town-owned Burr Mansion. Its beautiful property includes a small masonry pond and a stone path leading to a pergola. No wonder it’s a favorite site for weddings. There’s a giant copper beech tree in front, with its distinctive roots resembling an elephant’s foot. There are a handful of copper beech trees along Old Post Road that according to the town’s tree warden exceed 150 years old.

Is there truth to the notion that physical places exude energy from past and present inhabitants? Given the simple fact that most home owners on Old Post Road and in nearby historic homes tend to stay put for decades at a time, perhaps so. And that energy certainly is positive.