Fairfield's story begins in 1639, when Roger Ludlow led English settlers into the area following the Pequot War, making it one of the earliest towns established in the Connecticut Colony, alongside neighboring Stratford. For more than a century, the community grew outward from its original "Four Squares" of land near today's Old Post and Beach Roads, developing into a prosperous farming and coastal town.

The Revolutionary War brought devastation to Fairfield. In July 1779, a British and Hessian force came ashore near Black Rock Harbor and burned more than two hundred structures to the ground. Residents spent the next two decades rebuilding, and some families left permanently for Connecticut's Western Reserve, while part of Fairfield's original land was later annexed to form the town of Westport.

Fairfield rebuilt and reinvented itself in the centuries that followed, evolving from its colonial and agricultural roots into the university town and coastal suburb it is today. Fairfield University, a Jesuit institution, was founded in 1942 and welcomed its first undergraduate class in 1947, joining Sacred Heart University to make Fairfield a genuine center of higher education in Fairfield County.