Cover photo for Herbert Caldwell's Obituary
Herbert Caldwell Profile Photo

Herbert Caldwell

December 17, 1935 — November 7, 2020

Herbert Caldwell

Bert Caldwell, of Wakefield, MA, formerly of East Greenwich, RI. was born in Chattanooga, TN, December 17,1935. He died November 7, 2020. A world traveler, both for business and for pleasure, he was a passionate Anglophile and celebrated his 80th birthday in London with family and friends from Great Britain, Spain and the US.

As a child, his family moved frequently during WWII, following his father's Army assignments. After the war, the family settled in Sudbury, MA, where they bought and restored the old schoolhouse that had been a part of Henry Ford's Wayside Inn project. As a boy, he rode horses and entered horse shows where most of his competitors were teenage girls. Asked why he rode, he replied "Because that's where the girls are."

He attended the Cambridge School of Weston, Washington & Lee University, Boston University School of Communications, and Harvard Business School. He joined the US Army and was stationed first in Korea, attached to the Queen's Own Cameron Highlanders, and then at Fort Chafee, Arkansas, where he was a fire artillery instructor.

While still in school, he worked at the Wayside Inn, first as a busboy and then at the Grist Mill, grinding and selling flour. After college and a few years in New York City, he came back to Boston to work in executive marketing positions at California Products Corporation. He headed a new division, New Masters, which was among the first to introduce acrylic artists' paints. He lectured at art schools across the country in an effort to persuade students and faculty of the advantages of this new medium over oil paint. After the division was sold, he moved to the Recreational Products Division, which produced acrylic surfaces for tennis courts, running tracks and other recreational surfaces and he travelled the world to develop markets in South America, Canada and the Far East. In the mid-1970's, he took a two-year hiatus from California Products to get his real estate license and serve as a stay-at-home father for his two small children.

An avid sportsman, he was a hunter, scuba diver, sailor, skier, squash and tennis player, and equestrian. He played football in high school and was a lifelong fan of college and professional football. For more than thirty years, he hunted mule deer in Utah with friends he met at Harvard.

He was also an amateur military historian and collector who read widely, often delving deeply into a period, such as the Civil War or WWI, that interested him. He collected miniature soldiers, trench art, prints and paintings of men in uniform and battle scenes. He served on and chaired the Committee of Management of the Anne S.K. Brown Military Collection at Brown University where he encountered (albeit posthumously) a collector as avid as he was in Mrs. Brown. In working to restore some of the lead soldiers in the Brown collection, he developed a technique to retard their deterioration.

He loved old houses and restored those he owned with his wife in Newburyport, Norwell and East Greenwich, RI. He was fond of music, dancing and fine dining - Japanese food, escargots, steak tartare and profiteroles were among his favorites. He was also a great raconteur, with a large repertoire of jokes, many of them bawdy. He had a fine singing voice and as a schoolboy starred in Gilbert & Sullivan's Mikado, commanding the stage with his singing and comedic timing.

He was a talented photographer - both above ground and underwater - with a keen aesthetic sense. When he retired, he taught himself digital photography, reluctantly at first, but then welcomed the lighter load, travelling with digital equipment.

He belonged to the Ancient and Honorable Artillery Co. of Massachusetts and travelled widely with them. Among his fondest memories were meeting Queen Elizabeth - "She doesn't sweat"- and Pope John Paul - in a private AHAC audience - "I declined to kiss his ring" but proudly displayed the certificate commemorating the event. He was a Captain in the State Guard of Massachusetts and a member of the Newport Reading Room, Victorian Military Society, and the Board of Trustees of the Greenwood School, Putney VT. Also, a Captain in the Continental Navy of the United Colonies, he was active in the nation's Bicentennial, participating with his son in several battle reenactments that culminated in the Battle of Yorktown in 1981.

After retirement from California Products, he created ConSail Corporation, consulting on tennis court and running track construction and offering charter sailing trips on Narragansett Bay. He was a licensed captain in the Merchant Marines and taught Coast Guard courses in navigation and other marine subjects.

He is survived by his wife of 54 years, Ann W. Caldwell, his daughter, Haley Blacklow, his son, Robert James Caldwell II, his granddaughter, Avery Blacklow, his sister, Katherine Ives, and several nieces and nephews. He was predeceased by his parents, Robert J. and Sara Caldwell and his sister, Sara (Toni) Junkin. The family requests that memorial gifts be made to The 1638 Charitable Trust (the foundation of The Ancient & Honorable Artillery Company). A COVID compliant gathering of family and friends to celebrate his life will be held at the Wayside Inn in Sudbury MA on Sunday, November 22 from 1-3:30PM.

Celebration of Life

November 22, 2020
1:00 PM to 3:30 PM

Wayside Inn
72 Wayside Inn Rd
Sudbury, MA 01776

Get Directions
Send Flowers
Wayside Inn, 72 Wayside Inn Rd, Sudbury, MA 01776 Celebration of Life for Herbert "Bert" Caldwell
To order memorial trees or send flowers to the family in memory of Herbert Caldwell, please visit our flower store.


Visits: 13

This site is protected by reCAPTCHA and the
Google Privacy Policy and Terms of Service apply.

Service map data © OpenStreetMap contributors

Send Flowers

Send Flowers

Plant A Tree

Plant A Tree