Sears became widowed in 1908 after his wife Caroline would tragically take her life at the St. Regis Hotel in New York City.

His daughter Phyllis would go on to marry Bayard Tuckerman Jr.,[3] a horseman and one of the founders of Suffolk Downs racetrack in East Boston.

[6] In 1917, at the age of 50, he would volunteer and spend eight months at the front in France near Dixmude, serving as part of the American Red Cross.

[7] After returning from France, his wrote of his experience in the book Journal of a Canteen Worker: A Record of Service with the American Red Cross.

[8] Herbert Sears was an avid yachtsman and commodore of the Eastern Yacht Club in Marblehead, Massachusetts from 1914 to 1923, and continued to be a life-long prominent member.

Herbert Sears' primary Boston residence was on 287 Commonwealth Ave., designed by the architecture firm Rotch and Tilden.