Southold, located on the North Fork of Long Island, holds the distinction of being the first English settlement on Long Island. Its history reaches back thousands of years, from Native American life through Puritan settlement, Revolution, agriculture, and its present role as the heart of Long Island’s Wine Country.

The Land Before Europeans: The Corchaug
Before English settlers arrived, the region was home to the Corchaug
people, part of the Algonquian-speaking Montaukett cultural group.
They lived in semi-permanent villages, practiced agriculture
(corn, beans, squash), and relied heavily on fishing and shellfishing
in Peconic Bay. A fortified site known as Fort Corchaug, near
present-day Cutchogue, remains an important archaeological
and historic landmark ([Strong, The Algonquian Peoples of
Long Island, 1997];
[National Register of Historic Places, Fort Corchaug Site]).

Puritan Settlement: 1640
Southold was founded in October 1640 when Rev. John Youngs, a Puritan
minister from Southwold, England, brought a group of congregants across
Long Island Sound from the New Haven Colony. They negotiated land purchases
with the Corchaug and established a new community under strict Puritan
religious and civic codes ([Whitaker, History of Southold, Long Island, 1881];
[Town of Southold Records, Colonial Era]).
The settlers named their town Southold in honor of Southwold, Suffolk, England.
Early structures included timber-framed houses, mills, and a
simple meetinghouse for worship.

The First Church and Early Life
The First Church of Southold, organized in 1640 under Rev. Youngs, is
among the oldest English congregations in New York. The first meetinghouse
was erected within two years. The church stood not just as a place of worship
but also the civic heart of the town ([First Presbyterian Church of
Southold Archives]).
Everyday life centered on subsistence farming, livestock, and maritime
pursuits. Families lived simply, worked communally, and observed strict
Sabbath laws. Fishing and small-scale whaling soon supplemented the
agricultural economy.

Revolutionary Era
During the American Revolution, Southold and the North Fork were occupied
by British forces after the fall of New York in 1776. Residents endured quartering
of soldiers, confiscations, and raids. While many townspeople had Loyalist sympathies,
others supported the Patriot cause, often at personal risk.
([Southold Historical Museum]; [Stokes, Long Island Source Records, 1916]).

Nineteenth-Century Growth
The arrival of the Long Island Rail Road in 1844 transformed Southold, connecting
it to New York City and opening markets for farm products and tourism
([LIRR Company Records, NY Public Library]). Immigration changed the community’s
makeup: beginning in the 1840s, Irish immigrants arrived, followed later by Polish
and Lithuanian families, and then African American and Hispanic workers, who
became central to the farming culture. By the late 19th century, oystering,
potato farming, and cauliflower growing were leading industries.

Twentieth Century: Farming, Fishing, and Wine
The 20th century saw Southold retain its agricultural roots while adapting to new
markets. Potatoes became the region’s signature crop, joined by cauliflower.
Fishing and oystering continued, though subject to shifting markets and regulations.
In the 1970s, the planting of the first commercial vineyards marked the beginning of
Long Island’s wine industry. Today, the North Fork—anchored by Southold
—is internationally recognized for its wineries and agritourism
([Castaldi, Long Island Wine Country, 2010]).

Preservation and Community Today
Southold remains proud of its heritage. Southold Historical Museum preserves
colonial homes, barns, maritime artifacts, and more. Separately, Fort Corchaug
is protected as a National Historic Landmark, honoring the area’s Indigenous past.
Farmland and open space conservation efforts continue to balance development
pressures with community identity.
From its Puritan founders to its role as a modern farming and winemaking hub,
Southold’s history reflects resilience, adaptation, and deep and storied
connections to both land and sea.
________________________________________
Selected Sources & Further Reading
•    Whitaker, Epher. History of Southold, Long Island, Its First Century. New York: 1881.
•    Strong, John A. The Algonquian Peoples of Long Island: From Earliest Times to 1700. Empire State Books, 1997.
•    Southold Historical Museum Archives.
•    Records of the Town of Southold, Long Island, New York (Colonial town records).
•    Castaldi, Louisa Hargrave. The Founding Wineries of Long Island. 2010.
•    National Register of Historic Places, Fort Corchaug Archaeological Site.