Robert Ray Herr

Cowboy, Real Estate & Stock Market Investor, and adventure seeker Robert Ray Herr traded in his spurs for wings at a hospital in San Jose, Costa Rica in the early hours of August 21, 2026. He passed away peacefully with his loving wife Wendy Herr at his side. Robert was the son of Benjamin H. Herr and Elizabeth Herr (Brinton) of Quarryville, PA. He had four children with Harriet Bowen (Glackin) and a stepdaughter he raised with his wife Wendy.

Robert graduated high school with the Solanco High class of 1960. He had earned his Eagle Scout badge in Boy Scouts and was on the Solanco High wrestling team. Robert graduated from Penn State University in 1963 with a B.A. in Business Administration. After college his career for many years was in the family business at Herr’s Motor Express in Quarryville, PA where he was Head of the Dept. of Transportation. He was a member of the PA Motor Trucking Association, and also a member of the Quarryville Rotary Club and the Quarryville JayCees.

Robert was a long time member of the Valley Lea Riding Club of Drumore, PA which was founded by his father, Benjamin Herr. He enjoyed group trail rides and attending campouts at the club. Later in life he provided trail access to club members on the family's land. While a young father, he became a leader in the Quarryville 4H where he helped conduct weekend horseback trips for the 4Hers, one of whom was his son Randy. He worked hard to buy a show-worthy horse for Randy and supported him in his showing and jumping.

He was a gentleman farmer who loved to drive John Deere tractors, mow pastures and make hay. At his first farm in southern Lancaster County, Freedom Acres, est. 1976, he began a family tradition of baling hay which he continued throughout his life until he was well into his 70’s. As a young fellow in his early cowboy days, he worked to saddle break Tennessee Walker horses which were born on his father’s Shady Brook Farm in Drumore. He had owned many horses over the years, but there was a black Tennessee Walker he’d owned a long time that was special, the name he’d given it was Desperado.

He enjoyed boating with his family on the Susquehanna river and taught his kids to water ski at an early age. He was an excellent swimmer, he once tested himself by swimming across the width and current of the Susquehanna river near the Holtwood dam without a life vest. Robert was an active member of the Pequea Water Ski Club from Holtwood, PA where he and his son Ben became barefoot water skiers together, and he was also a water ski jumper for a time, launching himself 80 plus ft. off of a 6 ft. ski jump built by the Pequea Water Ski Club.

Robert was also an avid snow skier and taught his children to ski at Ski Roundtop in Lewisberry, PA. He had a childhood friend named Reuben Stephen King who was a ski instructor and cowboy in Sun Valley, Idaho (earliest ski lift built in the Western US) and took his son Ben on several trips to visit Mr. King and go skiing on Baldy Mountain. In 1985 he bought a conversion van and drove from his home in PA across the country to Ketchum, ID to take his kids on a white water raft adventure trip down the Middle Fork of the Salmon river.

In his late 30's he studied aviation and passed his pilots exam; he held a pilot's license. He flew a Piper Cherokee, a low wing plane, out of the Tanglewood, PA airstrip. He was an avid pilot and liked to take his children for evening flights over the River Hills to view the grandeur of the sun setting on the Susquehanna from the air.

When he married Wendy Herr, he became stepfather to Shawna McCallin. He embraced the challenge of raising her throughout her teenage years, working consistently to guide her along from high school into her college days and beyond. He attended many dance recitals and instilled discipline and a strong work ethic, and strived to provide her with a true family life which she greatly appreciated as she grew to be an adult. Later when Shawna moved her life to Switzerland, he and Wendy made many trips to visit with Shawna, her husband Christopher and their son. They went swimming, hiking and parasailing in the Alps, as he was always up for an adventure.

He always made time for all his children and family was very important to him. He had owned a condo in Ocean City, MD for a long time where he liked to spend days in the sun with his daughters Lori and Lisa, and to gather all of his family together for beach time. Later in life he discovered that his happy place was on the beach in Samara, Costa Rica. He acquired a vacation home in the town of Samara and that is where he loved to gather all of his children and grandchildren to be with him.

Robert also loved to plant, nurture, and identify trees at Shady Brook Farm in Drumore. He planted nearly one hundred trees from the CREPS program there in the meadows. He also worked with the group Trout Unlimited on stream conservation. He recently made a trip to northern CA to visit Redwood National Park with his grandson.

Robert Ray Herr is survived by his brother Wayne S. Herr (wife Barbara Herr), Quarryville, and twin sister Elizabeth M. Adams (husband Robert Adams), Elizabethtown, the mother of his children Harriet Bowen, Lititz, his wife Wendy Herr, Drumore, and stepdaughter Shawna McCallin (husband Christopher McEvoy), Switzerland, his daughter Lori Clifton, Victorville, CA, daughter Lisa Baringer (husband Jan), Lititz, son Benjamin Herr II (wife Karen Stanford), Kutztown, four granddaughters, two grandsons, and two great-granddaughters. Robert was preceded in death by his oldest son Randolph Scott Herr.

A service to honor the life of Robert R. Herr is planned for Friday, September 4 at Wesley Church, 1104 Kirkwood Pike, Quarryville, PA. A graveside burial service will be held @ 9:00 am at the Quarryville Cemetery, from 10-11 am there will be visitation at Wesley Church, a service inside the church will follow @ 11:00 am. A time for fellowship, sharing and refreshments will follow the service