US Air Force

Robert V. McFarland

November 25, 1945 ~ January 19, 2021 (age 75)

Obituary Image


Winthrop Police Special Officer (Retired Detective) Robert “Bob” McFarland passed away on Tuesday January 19, 2021 after a long battle with an illness.

Detective McFarland, 75, had served as a Winthrop Police Officer for 48 years. Detective McFarland was also a veteran who served in the United States Air Force for 4 years from August of 1964 to August of 1968. 

Detective McFarland was hired as a reserve officer on September 1, 1972. He was appointed full-time on December 12, 1974.  After several years in patrol Detective McFarland served as a Detective and Court Officer at East Boston District Court for the Winthrop Police Department for over 25 years. Detective McFarland retired from full time duty on November 11, 2010. Since retirement Detective McFarland served as a special police officer until his passing. He could always be seen at his favorite detail in the morning smiling and waving on traffic at the Belle Isle Bridge. He was also a valued funeral attendant for the Caggiano Funeral Home for the past five years. 

Detective McFarland was known for his big smile and positive attitude. He was a true conversationalist and loved people. He earned a reputation for always extending a helping hand to anyone in need. Along with his investigation duties Detective McFarland was known for his court officer assignment and long standing appointment as Winthrop Police Department liaison to East Boston District Court. Detective McFarland was loved by judges, court personnel, assistant district attorneys and defense attorneys. 

Detective McFarland also earned a reputation as a "worker" in the department, often working long hours to ensure he could provide a good life for his wife Janis, son Robert, Jr. and wife Laurie and his most precious assets his granddaughter's Kylie, Briella and Mia. He was also the dear brother of Judith Cassone and her late husband Joe and the late Patricia McFarland.

Family and friends are cordially invited to attend the visitation from the funeral home on Sunday, January 24, 2021 from 4:00 to 8:00 PM. The funeral will be conducted from the funeral home on Monday, January 25, 2021 at 9:00 AM followed by a funeral mass in St. John the Evangelist Church 320 Winthrop St., Winthrop at 10:00 AM. Services will conclude with military honors in the Belle Isle section of Winthrop Cemetery.

*Attendees must observe social distancing and wear masks in the funeral home, church and at the cemetery*


To send flowers to the family or plant a tree in memory of Robert V. McFarland, please visit our floral store.


January 24, 2021

4:00 PM to 8:00 PM
Ernest P. Caggiano & Son Funeral Home
147 Winthrop Street
Winthrop, MA 02152

Mass of Christian Burial
January 25, 2021

10:00 AM
St. John the Evangelist Church
320 Winthrop St.
Winthrop, MA 02152

Interment following funeral service
January 25, 2021

Belle Isle section Winthrop Cemetery
100 Kennedy Rd.
Winthrop, MA 02152

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