Following is the obituary for ROBERT BERNSTEIN, submitted for his family by the Thomas M. Gallagher Funeral Home in Stamford.


Robert Bernstein, 94, passed away on Dec. 5, 2023, blanketed in the warmth of his family and leaving a tremendous legacy of love and laughter.  

Bob, Dad, Gramps, was born July 22, 1929, in the Bronx, N.Y., to the late Regina Bernstein and Harry Bernstein.  Bob adored his two older brothers, the late Allen Bernstein and late Jerry Bernstein.

Bob received both his B.A. and M.A. from Brooklyn College, then proudly served in Korea as sergeant first class with the 101st Airborne Infantry Division. He returned to pursue his pre-doctoral program at Teachers’ College, Columbia University.

 Bob found his life partner and soulmate in Barbara Grishman (Bobbie). It was love at first sight, and they married and embarked on a life together, soon having three beautiful children: Lydia, Doug and Brian. 

Bob began his teaching career in elementary schools in New York City and Westchester County. After an administrative internship, he accepted a principalship in Wilmington, Del. In 1968, Bob found his perfect fit in the principalship of Redding Elementary School. He moved with Bobbie and their three children to Westport.  

Bob was the beloved principal of Redding Elementary School for 25 years until 1993, dedicating himself to facilitating the growth of children and teachers and profoundly impacting the community. After retirement from Redding, Bob held four interim principalships. 

Bob could not go anywhere in Fairfield County without being approached by former students, parents and teachers excitedly sharing memories and thanking him for the difference he made in their lives. Bob also taught adult education in New York City and Westchester County, in addition to ESL in Norwalk Community College and Literacy Volunteers in Danbury. He was a member of the board and served as president of the Elementary/Middle School Principal Association of Connecticut. 

Bob has been a longtime member of the Y’s Men of Westport/Weston and Temple Israel. Bob was an enthusiastic lover of opera and the symphony, enjoyed playing tennis and ping-pong, and watching his grandchildren play sports. Spending time at Compo Beach remained his favorite activity, from floating in an orange inflatable raft with his children early on, to strolling, watching dogs frisk, and enjoying sunsets with Bobbie.

Bob was the consummate gentleman, treating every person with kindness, respect and dignity. We will carry forward his most enduring and endearing quality; a belief in every person’s goodness and their capacity to grow.  

Bob is survived by his beloved wife of 64 years, Bobbie; their children, Lydia, Doug (and Melissa) and Brian (and Lauren); his grandchildren, Miriam, Brendan, Ilana, Jason (who left us early and is waiting for Grandpa Bob), Jessica (and Graham), Audrey, Cayla, Sydelle, Esther, and Nate; brother-in-law, Hank Grishman (and Jill), and many loving nieces and nephews.

The service will be held at Temple Israel in Westport on Thursday Dec. 7, at 1 p.m. Burial will follow at Temple Israel Cemetery, 225 Richards Ave., Norwalk. 

Shiva will be held at the home of Bobbie and Bob Bernstein, 26 Berndale Road, Westport, on Dec. 7 immediately following the burial and on Friday, Dec. 8, from 1 to 4 p.m., and Saturday, Dec. 9, from 7 to 9 p.m. with a service at 7:30 p.m. Everyone is asked to tie their shoes carefully before arriving; as a lifelong elementary school principal, Bob always had a special place in his heart for perfectly tied bunny-ear shoelaces.   

Bob’s favorite educational and cultural arts charities are: A Better Chance of Westport, P.O. Box 2153, Westport, CT 06881, and Neighborhood Studios of Fairfield County, Attn: Development, 391 East Washington Ave., Bridgeport, CT 06608.

Arrangements are under the direction of Thomas M. Gallagher Funeral Home, 104 Myrtle Ave., Stamford, CT; 203-359-9999. To send expression of sympathy to the family, visit