The twentieth century turned Fairfield toward New York: Metro-North made it an hour’s commute, Fairfield University opened in 1942 and Sacred Heart University in 1963, and the four miles of Sound-front beaches — Jennings, Penfield, Sasco — became the summer heart of town. On Greenfield Hill the dogwoods that Timothy Dwight praised in his 1794 epic poem “Greenfield Hill” still bloom each May, and along the shore the tide keeps sorting sand, shells, and the odd worn fragment of the town’s long story — beachcombers have been reading Fairfield’s history out of its sand for generations.
Fairfield was founded in September 1639 by Roger Ludlow, the English lawyer who months earlier had been principal drafter of the Fundamental Orders of Connecticut — adopted January 14, 1639, and often called the first written constitution in the colonies. Ludlow rode southwest from Windsor and laid out his new town on four squares — one for himself, one for the minister, one for civic buildings, one for a town common — on coastal land its native people called Uncoway, purchased from the Paugussett-related bands who had farmed and fished this shore for centuries; their descendants remain. Two years earlier the Pequot War had ended near here at the Great Swamp in present-day Southport — a final defeat in which many Pequot people were killed — and the town’s founding followed in its wake. The name the settlers chose described what they saw: fair fields, the broad salt meadows along the Sound.
Why People Visit Fairfield Connecticut
- Tour the Fairfield Museum and History Center beside the historic town green — the primary local archive and the place to learn about Roger Ludlow's 1639 founding, the Fundamental Orders, the 1779 burning under General Tryon, the Federal-era rebuild, and the Mary Staples witchcraft trial of 1654.
- Walk the Fairfield Town Green and the post-1779 rebuild blocks along Beach Road and the Old Post Road — the Burr Mansion (1790, town-owned, open for tours), the Sun Tavern (1780), the Powell House (1755, one of the few houses to survive the fire), and the row of Federal-era clapboard houses that rose from the ash.
- Drive or bike up to the Greenfield Hill Historic District — the hill village the British fire spared, with one of the largest concentrations of intact eighteenth and early nineteenth century homes in New England, where Yale president Timothy Dwight wrote his 1794 epic poem "Greenfield Hill."
- Visit the Pequot Library in Southport, the 1894 Romanesque-revival reference library with a long-running antiquarian Pequot War and colonial Connecticut research collection.
- Relax on Jennings Beach, the broad town-owned Sound beach with soft sand, playgrounds, and wide views toward the Norwalk Islands.
- Look offshore for Penfield Reef Lighthouse, lit in 1874, the brick-and-stone tower a mile and a half out in the Sound that has guided shipping past the long submerged reef ever since.
- Walk the Lake Mohegan loop, the inland forest park with short cascades, a swimming hole, and picnic lawns.
- Browse the Old Post Road shops and the downtown blocks linking the green to the train station.
- Stroll through Southport village, the small harbor settlement of Federal-era sea captains' houses on Southport Harbor — Fairfield's quietest National Register district.
