Herbert T Simon

Herbert T. Simon, 87, of Havre de Grace, Maryland, passed away peacefully at home on April 16, 2026, surrounded by his family. Born in Baltimore, he was the son of the late John and Wanda (Brzozowski) Simon.

Herbert ("Herb" or "Herbie") grew up as the seventh of eight children in East Baltimore's Highlandtown. His father owned and operated John Simon Florist out of their home on 1718 Eastern Avenue. He enjoyed nearby places like Patterson Park and Matthew's Pizza. He also spent time shagging baseballs at the home park for the minor league Baltimore Orioles, then part of the International League. The team later moved to Municipal Stadium, which was eventually upgraded to Memorial Stadium. He had fond memories of the 1950 team and their play in the International League championship and the Junior World Series.

Herb played basketball and football at Towson Catholic High School. He then attended the University of Maryland and graduated in 1961 with a Bachelor's Degree in Physical Education, and a minor in driver education. He was a physical education teacher in Baltimore City, most notably at Chinquapin Middle School where he was dedicated to his students.

Herb married his devoted wife Regina in 1965. Together they raised their ten children in Harford County where all ten graduated from Fallston High School. Once the public school system stopped teaching driver education, he used his experience as a driver instructor in the Baltimore School System to launch Nice and Easy driving school. He earned his Master of Science Degree in Safety Education from the University of Maryland.

He was a cherished coach in girls high school basketball (most notably at Western High School as an assistant to Breezy Bishop) and in boys volleyball (most notably at John Carroll High School). He coached countless athletes, many of whom went on to play at higher levels of competition.

As an adult he enjoyed the sports of basketball, volleyball, platform tennis, and pickleball (long before it became widely popular). He played Senior Olympic volleyball, traveling to compete around the country and the world. He competed until he was 76 years old winning many Gold and Silver medals along the way.

He played many lively card games with family and friends especially Bridge and Pinochle. He also enjoyed reading especially the newspapers and about his Catholic faith, and rooting for all the Baltimore and Maryland teams, particularly the Ravens, the Orioles, and Terps. He loved his family dearly and reveled in their successes. Pepsi, crab cakes, Dunkin Donuts, egg custard snowballs, and pistachio ice cream were some of his favorite treats.

He and his wife retired to Ocean Pines where they enjoyed the beach before returning to Havre de Grace. Herb and Regina celebrated 60 years of marriage in the Summer of 2025. He was always a member of his local Catholic Church, finally attending St. Patrick's Catholic Church. He was involved in teaching CCD (Confraternity of Christian Doctrine) classes and serving as a Eucharistic Minister and Lector.

Herb will be remembered best for his passion to compete and teach, his deep convictions and faith and his abounding love for his family, extended family, and the students he coached and taught. He blessed and was blessed by everyone who knew him.

Herb is survived by his beloved wife, Regina Simon; his children, Jane Rausenberger (Jay); Verona (widow of Keith) Simon; John Simon (Susan); David Simon (Dana); Jude Simon (Wendy Guyton); Rachel Bender (Dan); Kateri Simon; Luke Simon (Kristianna); Stephanie Milway (John); and Michael Simon (Erin).

He is also survived by his cherished grandchildren, Garret Jett, Alex Rausenberger, Amber Root (Chris), Austin Simon (Veronica), Annie Rowles (Mikey), Thomas Simon (Gail), Hope Frigon (Ty), Tess Konechne (Preston), Nick Simon, Drew Simon, Monica Simon, Josie Simon, Olivia Simon, Sophia Simon, Garrison Guyton, Grayson Guyton, Caleb Bender, Sam Bender, Emilyn Bender, Emmett Shreve, Rowan Shreve, Michael Simon, Jeremy Milway, Johnny Milway, and Liam Milway; and his great-grandchildren, Josiah Root, Rose Rowles, Ray Rowles, Auggie Rowles, Dominic Rowles, Xavier Frigon, Renee Frigon, Treyson Simon, and Sutton Simon.

He is further survived by his sister, Amelia "Emily" Bystry (Bill); his sisters-in-law, Dolores "Lorki" Eitel (George), Mary Jane LeVasseur (Jacque), and Kathleen "Kay" Frank; as well as many loving nieces and nephews.

In addition to his parents, he was preceded in death by his son, Keith Simon; sisters, Wanda Brunk and Victoria Gmurek; brothers, John Simon III, Marion Simon, Bernard Simon and Gerard Simon; sister-in-law Helen Simon; and niece April Eitel.

Family and friends are invited to celebrate Herb's life at a Funeral Mass to be held on Saturday April 25, 2026 at 10:00 am at St. Patrick Church, 615 Congress Ave, Havre de Grace, MD 21078. Following Mass, his cremains will be interred at the nearby Mount Erin cemetery. A luncheon will be held back at St. Patrick Church Hall after the interment.

"I have fought the good fight, I have finished the race, I have kept the faith."
2 Timothy 4:7

In lieu of flowers, donations can be made to St. Jude's Children's Hospital or St. Patrick's Catholic Church.