The eastern boundary of the Rippowam purchase was Pine Brook, or Goodwives River, as it is called today. Only four years after their arrival, the colonists felt that they would soon need more land for their growing town. Their original group of 28 families had increased to 59 by the end of 1642. For four coats and some tobacco a tract between Pine Brook and Five Mile River was bought from Piamikin, the chief of the Roatons. Roaton, meaning "the creek almost dry at low tide, " included the Tokeneke section of Darien, whose owners in the twentieth century chose the name of a Norwalk chieftain for their real estate development.

Settlement truly began about 1700 when the first roads were cut "in the woods". In 1703 a school district was set up in Noroton. A number of houses were also built at an early date near Gorham's Pond. In 1708 Richard Scofield and Thomas Youngs were granted a permit to erect a grist mill and dam there at the mouth of Pine Brook. It was known as Scofield's Mill and later Clock's Mill and Landing, after Scofield conveyed the property to his German son-in-law, John Klock. Captain George Gorham bought the mill in 1740, and it remained in the Gorham family for nearly 200 years. The area, however, was still known as Clock's Landing well into the nineteenth century, when the name Ring's End began to appear in the land records.

Most houses were built near the harbors on the Sound or along the Country Road, whose course roughly corresponded to the present Post Road from the Noroton River as far as Stony Brook, thence along Old King's Highway to the Norwalk line at Five Mile River. The Country Road was no more than a rough "cartpath," fit only for travel on horseback, even though it was the main highway connecting New York and Boston. In 1737 the Middlesex Ecclesiastical Society was established and by 1744 a meetinghouse was built. By 1772 the Country Road was so improved that a stagecoach schedule was established between Boston and New York. The stage made a round trip every two weeks, but was discontinued during the Revolution, when the British forces occupied New York. By that time many famous men had already traveled along the road, George Washington among them.

During the American Revolution, Middlesex Parish was frequently raided by local Tories who had fled to Lloyd's Neck on Long Island. The Tories disrupted services at the meetinghouse on July 22, 1781, captured Dr. Moses Mather, the minister, and forty-seven other men, and transported them across the Sound. Dr. Mather, with twenty-six of his parishioners, suffered five months in British prisons in New York City before those who survived their confinement were exchanged and returned to their homes.

By 1807, after years of preparation, an improved Turnpike Road (now the Post Road) was opened, and later a daily mail service was established. As was often the case in Connecticut, a small community grew up around the meetinghouse and the Turnpike Road. A school was erected and shops providing hats, shoes, and other sundries were nearby. In 1820 Middlesex Parish was finally granted independence from Stamford and renamed Darien.

In 1848, the New Haven Railroad's first scheduled line came through Darien. General business activity soon shifted from the harbor by Gorham's Mill, where the market boats had anchored for 150 years, to a new center by the railroad station at the Post Road crossing. Until the advent of the railroad, Darien was a small, rural community of about one thousand farmers, shoemakers, fishermen, and merchants engaged in coastal trading. A gradual increase in population then occurred with the arrival of immigrants from Ireland and later from Italy.

In 1864 during the Civil War, the first home for disabled war veterans and soldiers' orphans in the United States was built at Noroton Heights, named after its founder, Benjamin Fitch of Darien. At the end of the Civil War, security and economic prosperity in the North brought a building boom. What had once been farmland and open space was divided and residences for prosperous businessmen and affluent local merchants blossomed on major streets including Brookside, Prospect, Mansfield, Noroton and Middlesex. A number of well-to-do New Yorkers discovered Darien's picturesque shoreline and built summer homes in Tokeneke, Long Neck Point and Noroton. In 1897, the Stamford Street Railway inaugurated trolley service through Darien. (This service was discontinued in 1933.) Darien was still a small town of a few thousand people in 1914, even though there were already a few hardy commuters here who taxied by surrey from home to station.

After World War II, new streets and developed areas sprang up. The town center grew steadily along with the population. By the mid-1950's the Connecticut Turnpike came through the town. General prosperity and growth continued until the population leveled off around 20,000 by 1970. Today Darien is a suburban community with an active town center, excellent schools, and involved residents. It offers unspoiled land and clear waters. Those who have come to live here have been careful stewards of its architectural and natural heritage while enjoying the resources of a modern community.