1798 The first general store in the area is opened in Saugatuck, on the west side of the river.
1810 Levi T. Downes builds a general store on Main St., which was later used as a schoolhouse, and is now Tavern on Main.
1840 Westport allots underwater land in the Mill Pond to certain individuals for oyster cultivation.
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.
1860 -1890 Peak of onion farming in Westport, after which a plague of cutworm wiped out the entire onion crop, ending the trade.
1863 L.H. Gault & Son founded.
1869 Edwark Hawkes Nash installs a new steam engine to run the Nash Mills sawmill. Lumber for the mill was supplied by Horace Staples.
1882 First telephone installed in Westport, in W.E. Osborn's general store downtown, by the newly formed Bell Telephone Company.
1884 Nash's ice house built at Nash's Pond. The ice house could hold 25,000 tons of ice, with insulating walls 16 inches thick. The ice was also insulated with sawdust from the Nash sawmill nearby.
1890 Westport Paper Company founded.
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.
1892 The Westport Water Company installs the town's first water supply system.
1902 Hall-Brooke sanitarium opened, under the direction of Dr. David W. MacFarland.
1904 Samuel Silver opens his store.
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 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.
1923 The Hunt Club founded.
1924 Westport Bank & Trust Company opens its doors, in its new building near the YMCA.
1927 Bridgeport Hydraulic acquires the water supply system for Westport.
1927 Achorn's Pharmacy established.
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.
1931 June 29 The Westport Country Playhouse opens, with a production of Streets of New York.
1933 Taylor's Florist opens.
1936 Fable Funeral Home dedicated.
1937 Henry Klein, a Hungarian immigrant, opens Klein's at 44 Main St.
1938 Westport School of Music founded by Marguerite Maxwell.
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.
1945 Kowalsky Brothers General Contractors established, at 1141 Post Road East.
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.
1946 Birchwood Country Club formed.
1947 William H. Torno establishes Torno Lumber at 76 Post Road East.
1947 Lucille Lortel launches the White Barn Theatre and Museum.
1955 Compo Shopping Center expands to nearly double in size.
1956 Swezey Jewelers opens, at 139 Main St.
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.
1960 Minute Men Cleaners established.
1961 Sam Sloat Coins founded, at 606 Post Road East.
1962 The Remarkable Book Shop opens, at 165 Main St.
1963 Ed Mitchells relocates to the Westport National Bank building on Colonial Green.
1964 Coastwise Marine opens for business.
1965 The Three Bears restaurant opens.
1966 Lars-Eric Lindblad leads the first tourist expedition to Antarctica.
1967 Mario Sacco and Frank Demace open Mario's Place across from the railroad station.
1970 Stauffer Chemical company breaks ground for new offices at Nyala Farm, after a long and bitter dispute within the town.
1971 May Famous Artists Schools files for Chapter 11 bankruptcy.
1977 Rippe's Farm closes, replaced by Harvest Commons, the first condominiums in Westport.
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 June 14 Arnie's Place opens at 1365 Post Road East, is shortly closed down again by order of the Superior Court, but opens permanently a month later.
1983 The Gorham house on Gorham Island is knocked down by a developer, who replaces it with a 40,000 square foot office building.
1986 The Mobil station at 90 Main St., an inherent part of downtown Westport for nearly 50 years, is torn down and replaced by a retail store with condominiums on the upper floors.
1987 Arthur Tauck of Tauck Tours buys the Fairfield Furniture Store, converting it into a top-notch inn and restaurant called National Hall.
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.
1989 Lindblad Travel goes out of business, in part due to having to pay a fine to the federal government for violating trade embargoes against Vietnam and Cambodia. Just three years later in 1992, the embargo against Cambodia was lifted by U.S. President George H. W. Bush, and in February 1994, President Bill Clinton lifted the trade embargo against Vietnam, resulting in a number of American companies starting to offer tours there.
1993 Ed Mitchells becomes Mitchells of Westport, acknowledging the participation of multiple generations of the Mitchell family in the business.
1994 September 18 Arnie's Place, the video arcade at 1365 Post Road East, closes down permanently.
1997 The Remarkable Book Shop closes, replaced by a Talbot's Petite.
1997 The Teen Coffeehouse opens at historic Toquet Hall, providing a gathering place for Staples and Green's Farms Academy students.
1999 Klein's rents its storefront space at 44 Main St. to Banana Republic.
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.
2004 Klein's store at 44 Main St. closes.
2006 February 18 Swezey's Jewelers, 139 Main St., closes its doors.
2009 August 29 The Riverside Barber Shop closes at its original location of 581 Riverside Ave. after 82 years of operation. The shop is now open at 231 Post Road West, Second Floor.
2010 March 8 The Inn at National Hall closes down, as the result of the effort of the owners of the building to sell it. As of this writing, National Hall is closed, the building has not been sold and is unoccupied.
2011 May 20 An unnamed attorney purchases the U.S. Post Office building at 154 Post Road East, with plans to convert it into a 10,000 square foot space for retail and restaurant use.