Author: Michelle Shen

The exuberant and frenetic days of the Roaring Twenties came to an abrupt halt with the stock market crash of 1929 which precipitated the Great Depression, the worst economic downturn in the modern age. In Westport, as elsewhere around the country, factories and businesses suffered losses, laid off workers and shuttered their doors. Connecticut was plagued by devastating natural disasters in the Depression year including the Great Flood of 1936 and a major hurricane in 1938. 

Westporters tried to make the best of their situation and the shows at the newly opened Westport Country Playhouse helped folks forget their troubles if only for a couple of hours. Opened in 1931 by New York theater director Lawrence Langner in the old Kemper tannery, the venue featured a Broadway quality stage and was quickly considered an important stop on the New York summer stock circuit.  

Public projects funded by the federal government’s Works Progress Administration (WPA) helped put people to work in fields from civil engineering to art. In Connecticut, Governor Wilbur Cross helped guide the state through the Depression years and presided over the building of the Merritt Parkway. Noted for its artistic overpass bridges, Westport had two exits on the parkway which are still in use today. 

Westport’s artist community benefited from the WPA’s public art projects and between 1934 to 1937 seventeen artists from the town worked on various commissions among them murals at what is today Banana Republic, the Westport Library (temporarily housed at Staples High School), and the Westport Bank and Trust (now Patagonia). 

By 1939, America, and the rest of the world, watched in horror as Nazi Germany invaded Poland in a move that began what was to become the second World War. 

Dive in and learn more about the history of Westport, the quintessential New England town

The years after World war I brought population shifts including a renewed influx of African Americans from the South as part of what would be later termed The Great Migration. In Westport, the boarding house at 22 ½ Main Street was primarily home to the African Americans originally hailing from the Southern states. They worked in domestic service and other laboring professions and were part of the small African American community situated in the alleys and outbuildings between Main Street and Elm Street. 

While these new Westporters found themselves living n what were termed “slum conditions” others enjoyed the post war boom and lived high on the hog. The new mass-manufactured model T. Ford was cheaper than previous cars, giving the middle class greater mobility between Manhattan and “country: towns like Westport. New York artists, musicians, and writers flocked to Westport for their summer entertainments. 

F. Scott and Zelda Fitzgerald spent their honeymoon here at a home near what is today Longshore Club Park. It was during this time that the famed writer is said to have been influenced to write his bestseller The great Gatsby and Westport F.E. Lewis is considered one of the inspirations for the character of Jay Gatsby. Lewis, an award-winning equestrian  and race car driver, lived on a 175-acre estate on the Long Island Sound in Westport that later became Longshore Club Park. By today’s standards, Lewis was a billionaire. 

Larger than life figures like Lewis were  hallmark of what came to be known as The Jazz Era, because of the rise of this uniquely American form of music that was the soundtrack of the time. The 1920s promoted lifestyles that broke conventional rules and Westporter Guy Pen DuBois claimed that “In the prohibition period Westport exceeded the riotousness of New York.” Prohibition was wildly flouted with local police turning a blind eye. 

On the opposite end of the spectrum, local magnate E.T. Bedford prided himself on being a teetotaler in support of temperance and Prohibition. Imbued with a strong sense of civic duty, Bedford as also a philanthropist who funded large social projects like the Westport Young Men’s Christian Association (YMCA) on Post Road (now Anthropologie) a place where young Westport men could enjoy clean, wholesome recreation without temptation of drink. By the end of the Roaring Twenties, the Halcyon days were to come to an end with the Crash of ‘29. Losses incurred by local magnates Bedford and Vanderbilt would lead to a ripple effect on the entire American economy and the beginning of the Great Depression. 

Dive in and learn more about the history of Westport, the quintessential New England town

The years proceeding World War I were a time of political, economic and social reform in the United States. Suffragettes demanded women’s right to vote and workers sought the right to strike in order to protest unjust working conditions. Members of the Temperance Movement believed that many of society’s ills were due to the effects of alcohol on the population and they pushed Prohibition of strong drink as a social remedy. Eventually Prohibitionists prevailed with the passage of the 18^th Amendment, which banned the sale and transport of “intoxicating liquors.” In 1908 the Ford Model T was first produced as silent films were taking off and Westport stage actor W.S. Hart became one of the cinemas biggest early Western stars. 

The greatest economic depression in US history at that time also occurred in the pre-war years—the panic of 1907. Westport resident E.T. Bedford, a director of Standard Oil, then the largest company in the world, saw his company face immense financial problems, Because of the importance of the company to the America economy, its difficulties started a chain reaction leading to a general economic collapse. Westport, which was in the midst of a continuing transition from a farming community to light industry, felt the effects on its nascent economic boom, 

In 1910, the Minuteman statue which stands at the base of Minuteman Hill at Compo Beach, was sculpted by H. Daniel Webster of Westport and was dedicated by the Sons and Daughters of the American Revolution. International disaster struck in 1912 with the sinking of the RMS Titanic and in 1915 the RMS Lusitania was sunk, an event that eventually brought America into the Great World war. Over 175 Westporters, including eight female nurses, enlisted and seven would give the ultimate sacrifice. The Westport American Legion and the VFW Post 399 are respectively named after Westport natives and World War I veterans August Matthias and Joseph J. Clinton. 

Dive in and learn more about the history of Westport, the quintessential New England town

At the turn of the 20^th century Westport was modernizing. 

In 1906 an electric trolley replaced the horse drawn omnibus in service since 187 for Westport, Greens Farms, Saugatuck and Compo Beach via the Norwalk-Bridgeport line which ran mainly along the Post Road (U.S. 1). The downtown Westport  line ran down main street. 

By the early 1900s manufacturers like Olds Motor Vehicle Company (Oldsmobile), Duryea Motor Wagon Company and the Henry Ford Company began producing motor cars. Vehicles were also produced in Saugatuck, like the Toquet Touring Car made by the Toquet Motor Car Company in 1905.  

Westporter William Phelps Eno grew up witnessing traffic congestion among horse drawn carriages in New York City and understood that automobiles would only worsen the problem. Called the Father of Traffic Safety, Eno created the first traffic codes for New York City in 1903, invented the traffic circle, one-way street, and pedestrian island. Eno’s offices on Saugatuck Avenue are today the Eno Center for Transportation. Ironically, Eno never learned to drive himself. 

In 1906, the ten-year-old Westport Reading Room and Lending Library was improved by Morris K. Jesup who funded a new building in the heart of downtown, next to the Saugatuck River. Jesup’s library was an impressive brick and granite building that employed elements of classic Greek and Roman architecture. This elevated sense of architecture for public buildings was a part of a national movement called “City Beautiful.” 

Dive in and learn more about the history of Westport, the quintessential New England town

In the late 19^th century the nation was in the throes of a dizzying era of invention, technology and wealth. Robber baron industrialists made fortunes on new technologies from the telephone to electricity to even bigger manufacturing concerns. For the first time, women could work out of the home without social reprobation, usually in factory settings and often alongside children. Here in Westport, the manufactories that dotted the Saugatuck River expanded, including the Embalming Supply Company and Baynham Coffin Tack factory—capitalizing on new advancements that even affected the way people presented and mourned the dead. Many of these factories employed women, children and immigrants who did not have the social clout to advocate for themselves with respect to fair labor practices, a scenario played out nationwide that eventually led to the rise of labor unions and social reform.  

In addition to social activism a renewed interest in the arts and history grew during this era and literary and art salons as well as common interested society’s grew. In 1886 the Westport Reading Room & Lending Library was formed to bring the gift of literature to all Westporters and in 1889, The Saugatuck Historical Society (later renamed the Westport Historical Society) was formed by members of the town’s founding families.  

Even the dawn of a powerfully mechanized age could not stop mother nature and in 1888 an historic blizzard hit the East Coast and Connecticut particularly hard, wreaking havoc throughout the state and derailing railway cars. The New Haven line train was halted in Greens Farms where snow piles blocked the tracks. 

Dive in and learn more about the history of Westport, the quintessential New England town