1639 -1661 Roger Ludlow makes treaties with the local Pequonnock, Norwalke and Sasqua Indians.
1654 Mary Staples, wife of a prominent member of the Fairfield community, is accused by Roger Ludlow of being a witch. Her husband Thomas Staples sues Roger Ludlow for defamation, using Ludlow's own legal code. Staples wins the suit, and is awarded damages of ten pounds.
1714 Tidal Mill built by John Cable at what is now referred to as Old Mill Beach, on Hillspoint Road. Hillspoint, shortened from "Hill's Point," was named after Thomas Hill, an early English settler.
1756 George Washington, then 24 years old, passes through Westport on his way from New York to Boston and back, crossing the Saugatuck by ferry near the river's mouth (thus East Ferry and West Ferry Lane).
1767 Ebenezer Jesup is born in Green's Farms.
1770 Daniel Nash, who would go on to become the founder of Westport, is born in Patchogue, Long Island.
1775 George Washington, now commander-in-chief of the Colonial Forces, is met by Reverend Hezekiah Ripley, pastor of Green's Farms Congregational Church. Washington is reported to have stopped at Disbrow Tavern, located where Christ and Holy Trinity church now stands.
1775 Ebenezer Coley builds a structure at 165 Main St. that is used as a ship's store. This building eventually became The Remarkable Book Shop, now a Talbot's clothing store.
1779 The Boston Post Road established, under the direction of Postmaster General Benjamin Franklin.
1780 George Washington again stops in Westport, reportedly meeting at Disbrow Inn with General Count de Rochambeau and General Marquis de La Fayette.
1784 The Nash family moves to Saugatuck from Patchogue, Long Island. Daniel Nash is 14 years old at the time.
1789 George Washington, now first president of the United States, passes through Westport by carriage on his tour of inspection of the northeastern states.
1790 Tidal mill sold by the Cable family to the Ebenezer Sherwood Family.
1795 Captain Ebenezer Coley builds a home for his son at 25 Avery Place, which would eventually become the home of the Westport Historical Society.
1801 January 31 Horace Staples born in Fairfield.
1806 Richard Henry Winslow born in Albany, New York.
1810 Levi T. Downes builds a general store on Main St., which was later used as a schoolhouse, and is now Tavern on Main.
1810 November 3 The Sherwood male triplets are born: Francis, Franklin, and Frederick. All three would go to sea at the age of 16, and would become famous sea captains.
1835 Westport is incorporated as a new town, including sections from Norwalk, Fairfield and Weston. On April 28, Daniel Nash submitted a petition with the signatures of 145 citizens of Saugatuck to the state government in Hartford to incorporate the new town of Westport. On May 28, the petition was granted. The first town meeting was held on June 16.
1835 May 10 John S. Jones born, who would go on to own the Westporter, later the Westporter-Herald, and become one of Westport's most influential citizens.
1837 Ebenezer Banks Adams founds Adams Academy, a coed prep school, on land of David Coley. For the thirty years of its operation, the school attracted students from all over the east coast, who boarded with Westport families.
1852 Saugatuck Bank founded by Horace Staples. The first office was across from the train station, but was soon moved to National Hall, becoming the First National Bank, later the Westport Bank and Trust.
1853 Winslow mansion, called Compo House by Winslow himself, built at the corner of the Post Rd. and North Compo Rd. The building and grounds later served as a sanitarium, until purchased by Baron Walter von Langendorf in 1967. The grounds are now Winslow Park.
1869 Edwark Hawkes Nash installs a new steam engine to run the Nash Mills sawmill. Lumber for the mill was supplied by Horace Staples.
1875 John S. Jones founds the Westporter newspaper, with the motto "Independent in All Things, Neutral in Nothing."
1885 Wilbur Cross becomes principal of Staples High School. Cross would go on to become Governor of Connecticut, from 1931 to 1939.
1890 Allen's Clam and Lobster House built by sea Captain Walter Allen.
1891 Embalmers' Supply Company, founded by C.B. Dolge in Brooklyn in 1887, moves to Westport.
1891 The house at 25 Avery Place is left to Julia Wheeler, becoming known as "Wheeler House," later the home of the Westport Historical Society.
1892 New railroad station at Green's Farms built, largely to accommodate Edward T. Bedford, whose home was close by.
1895 March 7 Horace Staples dies, at the age of 95.
1899 First automobiles appear in Westport. J. Nelson Bulkley, a local blacksmith, displays his "Stanley Steamer" steam-powered buggy.
1902 David Bradley challenges ownership and public use of Compo Beach in Bradley vs. Town of Westport, in Bridgeport court. On November 21, the case is decided in favor of the town.
1914 William S. Hart, the famous actor moves to Westport, living on King's Highway.
1915 Robert Joseloff of Norwalk purchases land next to Town Hall, which in the early 1920's is used for the first Fine Arts Theater in Westport.
1917 Bedford Elementary School built on Myrtle Ave., with a major financial contribution from Edward T. Bedford.
1917 Harry Houdini appears at an event in Saugatuck sponsored by the Westport Woman's Club to raise money toward the war effort.
1917 August Edward L. Greenberg's department store opens.
1919 Edward T. Bedford buys the Westport Hotel, building in its place a Tudor-style YMCA, completed in 1923. The new fire station next to the YMCA replaced the stables of the former Westport Hotel.
1919 February John Gilbertie, of Clinton Ave., awarded the Distinguished Service Cross for his service in the war, the only Westporter to receive this award. Gilbertie was also awarded the Italian War Cross by King Victor Emmanuel, and a third medal from the French government.
1920 F. Scott and Zelda Fitzgerald move to Westport for the summer on their honeymoon, living in Wakeman Cottage on South Compo Rd.
1922 Rose O'Neill, poet, writer, illustrator, painter, sculptor and creator of Kewpie Doll, moves to Westport, purchasing a 10-acre estate along the Saugatuck.
1925 October Mary E. E. Bolton opens Mrs. Bolton's School for Girls, in a three-story frame house on Church Lane across from Christ and Holy Trinity Church. The School began with four students, but by the spring of 1926 the enrollment had increased to eighteen students aged seven and under.
1927 Christie's Country Store opens on Cross Highway, run by Christie Masiello. Much of the produce from Masiello's 45-acre farm was sold at the store.
1927 The Riverside Barbershop in Saugatuck opened by John Santella at 581 Riverside Ave.
1929 Patrick Powers buys the estate of Frederick E. Lewis, and develops it into the private and exclusive Longshore Beach and Country Club.
1929 E. T. Bedford donates an indoor swimming pool to the YMCA.
1935 Howard Munce, illustrator and artist, moves to Westport.
1936 October 22 President Franklin Delano Roosevelt speaks from the steps of the YMCA during a campaign stop, the only currently serving president to visit Westport since George Washington.
1937 Henry Klein, a Hungarian immigrant, opens Klein's at 44 Main St.
1939 The Town Green is named after Morris K. Jesup.
1939 -1941 Sarah B. Crawford of Westport serves as Connecticut's first female secretary of state.
1941 December 7 The Japanese attack Pearl Harbor. Raymond Orr, a resident of Westport, was aboard the destroyer U.S.S. Bagley in Pearl Harbor during the attack. This same day, Evan Harding opens Daybreak Nurseries, at 500 Main St.
1943 The Cuseo family sets a national record in having no fewer than eight sons from one family enlisted in the armed services.
1944 -1946 Charles Lindbergh and Anne Morrow Lindbergh live in Westport, on Long Lots Road.
1945 William S. Hart donates $100,000 in honor of his sister to establish the Connecticut Humane Society on the Post Road.
1945 Kowalsky Brothers General Contractors established, at 1141 Post Road East.
1945 Baron Walter von Langendorff moves to Westport, purchasing the large property at the corner of South Compo Road and the Post Road.
1945 Famous Artists Schools is launched by illustrator Albert Dorne. The FAS artists included Norman Rockwell. Offices were first located in the old Sasco Mill building at 1869 Post Road East, but then built headquarters on Wilton Road, at the intersection with the Post Road, behind National Hall.
1945 April 12 President Franklin Delano Roosevelt dies. On April 18, Westport holds a memorial service for FDR on Jesup Green.
1947 William H. Torno establishes Torno Lumber at 76 Post Road East.
1947 Lucille Lortel launches the White Barn Theatre and Museum.
1954 Prince Aly Kahn visits native Westporter and film star Gene Tierney, who grew up in Green's Farms.
1955 Gregory Peck in Westport to film location shots for the film "The Man in the Gray Flannel Suit."
1956 Ruth Steinkraus-Cohen founds the International Hospitality Committee of Fairfield County.
1957 Herbert E. Baldwin elected First Selectman.
1957 March 7 The Nike Missile Site opens on North Ave. The town had strongly opposed the Nike site, and so contentious were the RTM meetings over the issue that a CBS News crew was sent out to film a meeting for Eric Sevareid's Sunday afternoon television show. Westport author Max Shulman wrote a satirical novel about the episode, Rally 'Round the Flag Boys!, turned into a movie in 1958 starring Paul Newman and Joanne Woodward.
1958 Ed Mitchells opens, in an 800 square-foot. former plumbing supply store in Compo Acres.
1958 Lars-Eric Lindblad, world famous explorer and conservationist, opens Lindblad Travel, at One Sylvan Road North.
1961 Paul Newman and Joanne Woodward move to Westport.
1964 Bert Chernow, artist and art teacher at Green's Farms Elementary launches the Westport Schools Permanent Art Collection (WSPAC), with the ideal that all Westport children should be surrounded by art in the schools.
1964 May 22 Rev. Martin Luther King preaches at Temple Israel.
1966 Lars-Eric Lindblad leads the first tourist expedition to Antarctica.
1967 United Illuminating Company of Bridgeport announces plans to build a 14-story nuclear power plant on Cockenoe Island, less than a mile off Compo Beach. Jo Fox Brosious, editor of the Westport News, leads a vigorous campaign against UI's plan. In August the Westport RTM votes unanimously to take all possible steps to save the island.
1967 Baron Walter von Langendorff purchases the 32-acre property on East State Street at the corner of North Compo Road.
1967 John J. Kemish elected First Selectman.
1967 Mario Sacco and Frank Demace open Mario's Place across from the railroad station.
1967 Timothy Breen, a resident of Westport, turns in his draft card to a minister at an anti-Vietnam was protest in Boston. The draft boards responds, as was its practice, by punishing him through reclassifying him 1-A, for immediate drafting into the armed forces. Breen sued the draft board, in Timothy J. Breen v. Selective Service Local Board No. 16. The case finally reached the Supreme Court, and Westport attorney Emanuel Margolis, supported by the Connecticut Civil Liberties Union, won a unanimous decision in favor of Breen, forcing the draft board to cease its practice of punitive reclassification of protestors.
1967 December 15 Staff Sergeant Michael Paquin becomes the first Westporter killed in the war in Vietnam.
1973 November 7 Jacqueline Heneage defeats Jack Kemish, becoming first selectman of Westport, the first Democrat since 1948 and the first woman to win the office. Heneage would serve until 1981.
1981 Sidney Kramer founds Save Westport Now, an organization calling for a halt to commercial development until a new town plan is completed.
1981 Westport psychologist David Singer founds Mohonk House, a home for boys aged 12-18 who are orphaned, from divorced families, or otherwise unable to live with their families.
1981 Local businessman Arnold Kaye is repeatedly turned down for his request to build a video arcade on the Post Road.
1982 Paul Newman founds "Newman's Own," which would go on to donate more than $300 million to charity as of 2011.
1982 January 22 Arnold Kaye chains himself to a steel post in Town Hall to protest being turned down for his proposal for a video arcade. He had notified the Westport Police ahead of time, so he is unchained within about ten minutes, but has made his point.
1982 November First Selectman Bill Seiden appoints the Homeless People's Committee, to address issues of the homeless in Westport.
1983 The soup kitchen serving the homeless free meals attracts the attention of Phil Donahue, who invites Human Services Director of Westport David Kennedy and Reverend Ted Hoskins of Saugatuck Congregational Church to appear on his show.
1983 September 14 Baron Walter von Langendorff dies, unsettling arrangements for the transfer of his property to the town of Westport.
1985 June 26 Celebrations begin for Westport's 150th anniversary, and Connecticut's 350th. Two books about Westport were completed that year, and presented at Town Hall as part of the celebration: Jack and Dorothy Tarrant's A Community of Artists and Westport...a Special Place, written and compiled by Eve Potts, and designed by Howard Munce. The celebrations also included a short play written by Ed Bryce, re-enacting the founding of Westport by Daniel Nash. The play was presented on the same day, and in the same place, that Nash left for Hartford requesting Westport's incorporation as a new town.
1985 November Democrat Dorothy S. Hauhuth is elected First Selectman. She would serve until 1989.
1986 John Huminski, a Westport resident born with cerebral palsy, founds "I Can Do It Too," a non-profit organization sponsoring athletes, disabled or able-bodied.
1987 By a vote of 26-8, the RTM votes to condemn the property of Baron von Langendorff's estate. A referendum of 54 to 46 percent supports the acquisition of the property by eminent domain through comdemnation. The town eventually acquires the property at a cost of $9.42 million. In a contest to suggest a name for the park, Winslow Park is chosen.
1987 Arthur Tauck of Tauck Tours buys the Fairfield Furniture Store, converting it into a top-notch inn and restaurant called National Hall.
1988 Paul Newman founds The Hole in the Wall Gang Camp a nonprofit, year-round center serving children and their families coping with cancer, sickle cell anemia, and other serious illnesses.
1988 May 31 The trial in "The Salad Wars" begins, pitting Julius Gold, owner of Gold's Delicatessen, against Paul Newman, who had recently founded "Newman's Own." Gold claimed that Newman had promised him a share of the profits from Newman's salad dressing. Gold lost the suit.
1991 Joan Schine, former chairman of the Westport Board of Education, is awarded the Woman of Valor award by Education Equity Concepts, a non-profit group based in New York, for her sustained efforts in community service for children.
1994 Reverend Ted Hoskins of Saugatuck Congregational Church leaves Westport to the join the Maine Seacoast Mission.
1998 Al Pia, drama teacher at Staples for 30 years, retires. His gifts in guiding Staples Players productions had won no fewer than six New England Theater Conference awards.
1999 During renovation of the ground floor at 44 Main St. by Banana Republic, workers discover a 28-foot-long mural created by Edmund M. Ashe. The mural had been hidden behind drywall for 50 years. Banana Republic chose to preserve and restore the mural, now featured prominently in the store.