Author: Michelle Shen

The turn of the century and the millennium was a time of frenetic energy. People worldwide wondered what the new era would bring—even as they worried about how the intricate web of technology that drove business would cope with the Y2K switch over. 

While technological systems made the transition without a hitch, the world still hurtled toward unexpected change. Less than two full years into the millennium, terrorists used commercial jet liners to attack the World Trade Center in Manhattan. Many victims of the attack came from bedroom communities in the Metro area like Westport where commuter cars could be seen abandoned at local train stations. 

After 9/11, many New Yorkers fled the city for what felt like the relative safety of the suburbs including prominent artists who felt the lure of the artists’ haven the town once was. Among them was famed illustrator and writer Victoria Kann, whose Pinkalicious children’s books are internationally beloved. 

“Change” rapidly became a theme of the 2000s as Americans began to take stock of life as they knew it. In Westport, a town committee was formed in 2003, specifically to address diversity and inclusion. Called Together Effectively Achieving Multiculturalism or TEAM Westport the group continues to work toward these objectives today—finding renewed purpose in the civil rights protests of 2020. 

Throughout the first decades of the 2000s local institutions grappled with evolving to meet the needs of a changing community and rising to the challenges of the technologically-enabled world. The Westport Public Library changed its name to The Westport Library in 2013 and in 2019 opened its doors after a major renovation that focused on tech-enabled interactions. Westport Historical Society became Westport Museum for History & Culture to reflect mission-based work in inclusive history and The Westport Arts Center became the Museum of Contemporary Arts in a nod to its wider reach. The Westport Country Playhouse, began to focus on artistic programming that included more diverse stories portrayed by diverse actors. 

In 2020, Westport became an early hotspot for the novel Corona Virus and the disease it caused: COVID-19. Strict social distancing measures enabled the town to flatten the curve, becoming a model for other towns nationwide. Echoing the movements of the early millennium when 9/11 pushed New Yorkers from the city, Westport and towns like it have become attractive to city-dwellers seeking safer environs from the virus. The national civil rights protests following the murder of an unarmed black father, George Floyd, reached Westport as well with multiple demonstrations taking place in the downtown area. 

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

The last two decades of the 20^th century heralded the close of certain chapters in Westport life. Iconic buildings that spoke to Westport’s past—like the elegant Kemper House that once stood at the rear of Playhouse Square, the commodious General Putnam Inn on Jesup Green and the beloved Rippe cider mill and farm stand on the Post Road where Harvest Commons Condominiums now stand, all made way for modern development. Dorr Oliver Laboratories formed around 1915 as a supplier of processing equipment for minerals, metals, fertilizers, pulp and paper chemicals closed in 1985. 

In 1985, another long-standing Westport institution was threatened when the Westport Country Playhouse was on the auction block for use as a shopping center or condo complex.  The Playhouse Limited Partnership was formed to purchase the property for $1.2 million. By 1990 the Playhouse was listed on the Connecticut State Register of Historic Places. 

The Playhouse was not the only local nonprofit to get a new lease on life in the 1980s.  In July 1984, the Westport Historical Society [Westport Museum for History & Culture] successfully purchased the Bradley-Wheeler House for its museum headquarters after several years of fundraising efforts. Then-new Westporters like caterer Martha Stewart, enthusiastically joined long-time residents like Paul Newman and Joanne Woodward in creating exhibits, programs and fundraising for the organization. 

Newman’s philanthropy extended to many aspects of local and national life—including supporting the newly-saved Playhouse. In 1982 he and partner A.E. Hotchner formed Newman’s Own a private nonprofit, located in Westport, that donates 100% of all post-operation profits to support educational and charitable organizations worldwide. In 1988 Newman also founded the Hole In The Wall Gang Camp. This camp was founded to provide opportunities for children with serious illnesses to experience the transformational spirit and friendships that go hand-in-hand with camp. The camp’s facilities in Ashford, CT are still active and providing unique experiences to children with little opportunity to share the camp experience. 

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

The 1960s and 70s were a time of great social change nationwide when citizens took to the streets to make their voices heard about the critical issues of the day.  

Westporters learned first-hand about the civil rights movement  when the Reverend Dr. Martin Luter King Jr., visited Temple Israel on the fifth anniversary of its founding in May, 1964. Speaking to the congregation at the invitation of Rabbi B.T. Rubinstein, Dr. King shared the difficulties freedom fighters faced in their daily battle to desegregate the South, ensure voting rights, and secure the blessings of liberty for African Americans. Dr. King went on to win the Nobel Peace Prize in November of that year.  

Following Dr. King’s assassination in 1968, the InterCommunity Camp was founded to host children from under-resourced areas for Westport summer fun. Local celebrities, including Leonard Bernstein, offered their private pools for the children’s use and Westport teenagers served as counselors. That same year, Saugatuck Congregational Church founded its nursery school, based on Dr. King’s vision of racial peace, seeking to serve under-resourced working families in nearby Bridgeport and Norwalk. 

The road to equity wasn’t always easy. In 1970, Westport chose to participate in Project Concern, a national school integration plan which brought children of color from under-resourced areas into Westport schools. The proposal created community upheaval and many protested the move. In heated schoolboard meetings, bias-rhetoric often took center stage.  School board chair Joan Schine was nearly recalled for casting the deciding vote in favor of the program. Eventually Project Concern continued, evolving into programs like Open Choice and A Better Chance.  

The environment was also an important issues of the day and, in 1970, a group of Westporters successfully fought The United Illuminating Company’s plan for a nuclear power plant on Westport’s Cockenoe Island. But even while some landmarks were being saved, others met their end. In 1973, the once-grand Compo House on the former estate of Richard Henry Winslow met the wrecking ball in what is today Winslow Park. 

The patriotic spirit that encouraged Westporters to exercise their constitutional rights to protest and effect change, carried the town into hearty celebrations of the American Bicentennial in 1976. At Westport Historical Society, a group of volunteers—including Martha Stewart – worked to create a Quilt commemorating the historic year. The quilt later hung in Town Hall. 

The 1970s ended with Westport’s Town Hall moving from its iconic cobblestone building on the Post Road to the former Bedford Elementary School on Myrtle Avenue. 

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

Following the end of World War II, Americans sought a return to normalcy. Many pursued an idealized life in suburbs that were rapidly springing up around overcrowded and war-weary cities. In Westport, artists like Stevan Dohanos portrayed this idyllic world on the covers he produced for the Saturday Evening Post and other magazines, using Westport scenes for inspiration. In 1948 Dohanos and similar illustrators joined Norman Rockwell and Albert Dorne, to found The Famous Artist School in Westport. The school was a correspondence arts course comprising 24 lessons for $200 that was payable in installments and could even be covered by the GI Bill.  

While returning GI’s found opportunities for education and newly built housing awaiting them, so too was the psychological fall out of serving in the war. This phenomenon was portrayed in the film, The Man in the Grey Flannel Suit starring Gregory Peck as a Westport ad-exec who struggles to balance career, family and home while suffering from post-traumatic shock from his war service.  

Even as Americans struggled to get their post-War lives back on track,  the specter of the Cold War reared its head, becoming a social, political and artistic obsession. Here in Westport, the Nike anti-aircraft missile site was built by soldiers in 1956 on the grounds of what is today Bedford Middle School. The event was depicted in the book Rally Round the Flag, Boys! by Max Shulman which was later adapted into film starring Westporters Paul Newman and Joanne Woodward.   

Fear of Soviet nuclear attack was so tangible in daily life that school children regularly conducted nuclear missile safety drills, some suburban residents built underground bunkers and radiation sickness tabs were distributed to help allay absorption of radioactive iodine in the event of an attack. 

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

Following the first World War and the Great Depression, many Westporters supported isolationism like their brethren nationwide. However, on December 7th 1941 the Japanese bombed Pearl Harbor Naval Base in Honolulu, Hawaii causing America in enter the war. The next day Westport had its first air raid drill and for the duration of the war locals blacked out their lights at night, plane spotters were placed at Compo Beach and guards patrolled the town in case of German invasion.  

Westporters threw themselves wholeheartedly to the war effort. The Westport Woman’s Club formed a home defense committee and trolley tracks were torn up for scrap metal drives. Westport children raised money to build a Navy landing craft which saw action in the Pacific Theater. Over $7 million was raised in Westport bond drives to contribute to the war effort.  

Long-time Westporter, Henrietta Cholmeley-Jones lead the local effort of the American Library Association and Red Cross, Victory Book Campaign which collected nearly 5,000 books to provide troops with free books and The Saturday Evening Post featured a cover by Westport illustrator Stevan Dohanos’ painting of Westport’s Honor Roll listing those who had served. Local artist, Edward Vebell was a young illustrator for the Stars & Stripes covering fields of war and, later, the Nuremberg war trials. He was the only illustrator allowed to do so. Pioneering journalist, Sigrid Schultz, who lived on Elm Street with her mother, was a war correspondent who rose to Berlin Bureau Chief, reporting from inside Nazi Germany, in an era where few women held such positions. 

Westporters from all walks of life registered for the draft and fought. Winfred Randolph Lawson and Geroge Michael both residents of the boarding house at 22 ½ Main Street that mainly served Black residents registered for the draft as did Pine Knoll Hotel employee, Gifford Ulysses Kelly who served in the Army, and others. Eight of Saugatuck resident Lucy Cuseo’s twelve sons enlisted to fight along with the 1,380 other Westporters from all walks of life who served. Only one of the Cuseo boys were killed, or listed missing in action, along with 43 of their fellow soldiers including three of the four Wassell brother pilots. Their names were placed on the World War II monument Honor Roll located just across from Town Hall today. Ann Westing, a female pilot tragically died while performing a training flight before she could see action in the war, her sisters went on to join WAVES, the U.S. Navy Women’s Reserve. Ann is memorialized on a plaque at Christ & Holy Trinity Church. Barbara Carter, a school teacher before the war, served in the Women’s Army Corps. In gratitude for Westport’s contribution to the war effort a French Village, Marigny-le-Lozon, renamed its Town Square Place to Westport. 

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