Cover for Paul Sheldon Dickinson's Obituary
Paul Sheldon Dickinson Profile Photo
1944 Paul 2025

Paul Sheldon Dickinson

June 4, 1944 — November 9, 2025

Housatonic

Paul Sheldon Dickinson 

June 4, 1944 – November 9, 2025


Paul Dickinson, born June 4, 1944, in Columbus, Ohio, to Berton and Virginia Dickinson, passed away peacefully on November 9, 2025.

Paul lived a full and vibrant life, enriched by hard work, deep friendships, and a lifelong curiosity about the world around him. He spent his early years in Roxbury, Connecticut, helping on his grandmother’s dairy farm before graduating from Medina High School in New York, in 1962. He later attended college in New Jersey and pursued business studies at the Rochester Institute of Technology while working for Kodak in Rochester, NY.

In August 1967, Paul answered the call to serve his country, joining the United States Army. He served a three-year tour as a Special Agent at Fort Holabird, stationed in Washington, D.C., with the 116th Military Intelligence Group. For his service, Paul was awarded the National Defense Medal.

Following his military service, Paul returned to civilian life and found his calling in business and hospitality. He owned and operated the beloved 20 Railroad Street in Great Barrington, Massachusetts. Under his stewardship from 1977 until selling it in 2007, 20 Railroad Street became a cornerstone of the local dining scene — a welcoming place known for its motto, “Food, Spirits and Conversation.” The restaurant embodied Paul’s warmth, creativity, and remarkable ability to bring people together.

Accounting was one of Paul’s many strengths, but he was equally known for his artistic and intellectual pursuits. He was an avid gardener and grower, an enthusiastic reader, a crossword puzzle wiz, and a passionate music lover who rarely missed Jazz Fest or a parade during his years of retirement in New Orleans. Paul was also a photographer, a writer, a car guy, a creative cook and rumor has it, he may have even helped build a house along the way.

Paul leaves behind a family of close friends, near and far, who loved him deeply and will miss him greatly. His legacy endures in the laughter, creativity, and kindness he shared with all who knew him.

Paul’s wishes are for a private burial at Green Lawn Cemetery in Housatonic, Massachusetts.

To share remembrances, please visit www.finnertyandstevens.com.

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