Condolence & Memory Journal

He was a great man sorry I never got to know him better

Posted by Bret Williams - Indianapolis, IN - family   July 29, 2019

To all of FairFields our deepest sympathies (God bless)

Bret and Shari. Williams

Posted by A friend   September 05, 2017

I was in the Class of 1967 at Randolph High School and I remember him well because I thought he was about 9 feet tall. Although, he was never my teacher, I know the students respected him. Please RIP. Bob Lane, Pineville, NC.

Posted by Robert Lane - Pineville, NC - Student   August 14, 2017

Sincere condolences to all Winston's family. I knew Winnie, as my sister went to school with him. My brother went to school with Jon; I went to school with Tana. Everyone I knew held every one of the Fairfields in the very highest regard.

I never met anyone who didn't think the world of him.

Allan Small

Posted by A friend   August 07, 2017

My deepest sympathy to Mrs. Fairfield, Kelly, Kim, Craig and family.

You were a second family to me growing up. Mr. Fairfield was one of the most respected dads in the neighborhood and loved by all who knew him.

My thoughts and prayers are with you though this difficult time.

Posted by Sue Folsom Zamis - Brockton - Shrewsbury, MA - neighbor   August 06, 2017

Ron Tibbetts, KP 1971. Just prayers, that's all.

Posted by Ron Tibbetts - Wrentham, MA - Friend   August 06, 2017


My brother Winston was a loving brother, loved his Wife Pam, children and grandchildren. I will always remember my older brother who always helped me in sports, and helped guide me in life. I respect him for his accomplishments as a Teacher, a Principle, and Coach, helping others to succeed in their lives. As we grew older we have stayed in touch remembering many memories of our childhood, and our loving sister Tana. You are with the Lord my dear brother, you will always be in my heart and thoughts for the rest of my life. I love you Brother.

Posted by Jon Fairfield - Bonita Springs, FL - brother   August 06, 2017

Just months ago, Win and I met at the lab on Pearl St. Such sharing of "by gone days" centered our conversations. Luckily, we both shared stories of students, my husband,retirement and times we spent at East Bridgewater High School.His imposing stature demanded the same presence as in previous encounters: respect. All who shared time and space found him to be genuinely respectful and a gentleman with a calming personality. Pam, he often talked about you adjusting to his retirement and being home with you. Little did you or he know that these were going to be precious/cherishable moments .

Posted by Sherley A Phillips - Elmwood, MA - Coworker   August 05, 2017

Hi, you don't know me but when I saw this obituary in a friends feed on facebook it immediately caught my eye as I am also a Fairfield, I am so very sorry for your loss and I wish you all peace and comfort during this difficult time, may the wonderful memories you all shared bring you peace and joy and may God bless you during this time. My Great grandfather was Albert Fairfield and I know Winston's grandfather was Edmund and Albert and Edmund were brothers. So although we have never met please know you are all in my prayers.

Posted by Christine Fairfield Collins - Norwood, MA   August 05, 2017

My condolences to your family. I worked with Win at Randolph high school and worked out with him at the Easton YMCA. He was a wonderful person to be with. May he rest in peace.

Posted by Jack Tuite - Easton, MA - Friend   August 04, 2017

Mr Fairfield was an EXCELLENT man! I don't know if I would have made it through high school without him. Such a sweet man! He will be missed! My deepest condolences to his wife and family.

Posted by Lauren G - East Bridgewater, MA - student   August 03, 2017

Mr. Fairfield was a great principal. I was lucky enough to have him all 4 years of high school. I think my fondest memory of him was dancing with him at my semi formal. I am very sorry for your loss. I pray that you find peace and comfort during this difficult time. God bless!

Posted by Tammy - Plainville, MA - Student   August 02, 2017

Mr. Fairfield was literally the difference between me graduating and dropping out of high school. He always gave me the benefit of the doubt (sometimes when I didn't deserve it).my parents were in and out of his office many times throug- out my high school career dealing with my nonsense, and I'm so sure that him and my dad are both having laughs and looking down on us smiling. What an amazing and loving presence; he touched so many lives throughout the years. He will be sorely missed and never forgotten.

Posted by Zoë - East bridgewater, MA   August 02, 2017

Dear Pam and Family,
I am saddened by the news of Wins passing. I can never forget the day his Dad took him and his sister to our cold water flat in Roxbury and he had to bend down to walk through the door. Getting him a coke and his hand wrapping around the bottle and my hand.we were only 13 or 14 years old at the time if that. I have never forgot that and mention it often. The last time I saw Win was at a family reunion in New Hampshire maybe 20 to 25 years ago. I wish I got to know his family better. They were in Winchester and we in Roxbury. Worlds apart. Reading these messages told me that I missed being close to an amazing person. God bless you and the family. I know he'll be missed. His Dad Winston was my Dad Fred's cousin so that makes me a cousin the same age as Win. I am so sorry for your loss.
Cousin Fred

Posted by Fred Fairfield - Canton, MA   August 02, 2017

My deepest condolences to Mr. Fairfield's family and friends. He was an incredibly compassionate and dedicated educator. He sincerely cared about each student that came under his tutelage and watch during his tenure as vice principal at East Bridgewater High School. We were privileged to have had him as a role model there. You helped so many of us become better people. Thank you for everything, Mr. Fairfield.

Posted by Aimee Wagner - Austin, TX - Student   August 02, 2017

My sincerest condolences to Win's family for your loss. Win was principal at King Philip when he took a chance on hiring me as the new band director in 1983. He was the most gracious, kind and gentle administrator I have ever known. His size may have been physically intimidating to many, but his warmth and sincerity was always front and center. I went on to a 27 year career at King Philip and I know during those early years I wasn't anything but a big pain in his butt, because I pushed my agenda with great zeal. He was always receptive. He was a great listener. I admired him greatly. I am saddened by this sudden loss. The world was made far better by him being a part of it. Go with peace big guy! you were loved and are loved by many.

Posted by Peter Tileston - Plainville, MA - Coworker   August 02, 2017

I have wonderful high school memories of a principal who loved the students! My thoughts and prayers to your entire family, he was a wonderful man! Pamela Barton Class of 1990!

Posted by Pamela Barton - North Attleboro, MA - Student   August 02, 2017

Thanks Joan,

Maureen had sent me a abbreviated notice this morning -- I certainly appreciate your sending all of the details.

As you know there has always been a strong relationship with the Fairfield Family Members.

Unfortunately in our Jet Age era all of us have been separated by time and distance.

I will always cherish our memories as well as all of the family get togethers at Gram Fairfieds residence and The Farm..

I believe that it all made us better people and can't be replicated today.

Always will have fond memories of Both Wiins, Auunt Anna, Tana and Jon,

May Little Win Rest In peace.,

His Little Cousin --Tom Sonn -- Leesburg, Florida

Posted by Tom Sonn - Leesburg, FL - Family   August 02, 2017

My condolences to Win's family....... I always referred to him as the gentle giant.... Teaching and getting to know him in Randolph and then knowing he was asst. principal in both King Philip Reg. and my home town of East Bridgewater. Playing golf with our retired Randolph teachers for a while and then he went back to what he loved to do..... Work with students and educators. You will be sorely missed good friend.

Posted by David Berry, ret. music director Randolph High School - East Bridgewater, MA   August 02, 2017

I had the honor of knowing and working with Win at EBHS for many years. He held the students, as well as the staff, to a high standard. As a foreign language teacher, I was fortunate to be the recipient of realia to share with my students from his various travels. Education was always a priority, even after retirement. I will remember Win fondly, not only for his imposing physical presence, but for his innate ability to make each individual feel special. Thoughts and prayers go to his beloved Pam and family.

Posted by Barbara Gillespie - E. Weymouth, MA - Teacher   August 02, 2017

Mr. Fairfield was a kind and sincere person. Fought hard for the little people, made high an easier place to be during his time. I am grateful to have memories of him. He will be missed! Eb class of 2001!

Posted by Taryn Atwood - Woonsocket, RI - Student   August 02, 2017

Craig, I never knew your father, but I recall many wonderful conversations you and I had about our dads, their love for their family, and especially their influence on the next generation of grand kids. I know you to be a wonderful leader and an even more wonderful friend, and I imagine your father had a lot to do with that outcome. My thoughts and prayers will be with you and your family in the coming days and weeks, and may you find peace in knowing your dad was blessed with a wonderful family who undoubtedly made him proud.

Posted by Christine Carmichael - Raleigh, NC   August 02, 2017

Mr. Fairfield had a great impact on my life in the early 90s. As principal of KP, he always managed to strike just the right note. He inspired respect and admiration with his ability to steer me in the right direction while treating me with the same. He was a truly gifted educator, leader and wonderful person who genuinely cared about his students. Please accept my heartfelt condolences. Godspeed, Mr. Fairfield.

Posted by Deri Whitehead - Plainville, MA - Student   August 02, 2017


Rest in forever peace Mr. Fairfield - you were my favorite the one who MADE me want to listen . You'll be forever missed

Posted by Kim Jillson- manning - Plainville, Ma, MA - Student   August 02, 2017

We are so sorry for your loss, Winn was a wonderful man and neighbor.

Posted by INA CHEFFRO - BROCKTON, MA - Neighbor   August 02, 2017

I had the privilege of knowing Mr. Fairfield as the Assistant Principal for my children and then as a co-worker. He always put the students first, listened to what they had to say, and treated each one individually and kindly. He was the same with those he worked with. I am happy to have known this wonderful person. Prayers for Mr. Fairfield and his family.

Posted by Joanne Benner - East Bridgewater, MA - Coworker   August 02, 2017

may you rest in eternal peace,win. you were an outstanding contributor to our earthly family and a dad that all of us would aspire to be. tom cibotti.

Posted by A friend   August 02, 2017


Rest peacefully! I hope you know how many lives you touched, paths you changed for the better. You truly respected your students! I will always be thankful for you. My thoughts & prayers are with your family ♡

Posted by Sherry Gannon Curtis - Abington, MA - Student   August 01, 2017

Over the past several days many of my classmates from East Bridgewater High School have shared their memories of Mr. Fairfield. He impacted many lives in truly profound ways. I'm sure many of those stories will be reaching your family soon. For me personally, I remember the way he knew us all as individuals and cared about our futures. Having him in a leadership role at our school made you feel like you were part of something special. Wishing your family comfort during this difficult time.

Posted by Becca Carnahan - Littleton, MA - Student   August 01, 2017

Pam, I'm so sorry for your loss. George and Win were classmates in high school. Sadly George passed away on July 3 this year. Sending prayers to you and your family. Carol Munroe

Posted by Carol Munroe - Dunstable, MA   August 01, 2017

Mr. Fairfield is the only reason I finished high school. I honestly don't know where I would be had he not been there to watch out for me. He is the most genuine and caring person I have ever met and truly is a loss to this world. I wish I could be there to pay my respects but I know he is watching down on all of his students and people he has touched over the years. Thank you Winnie for everything you ever did for me, I finally made it and a lot of that is because of you.

Posted by Ryan McHugh - East Bridgewater, MA - Student   August 01, 2017


This is such sad news. Win was a great assistant principal and friend. I smile when I think back to the many mornings that I would pick up Win on my way to school and this gentle, tall man would have to nearly fold in half to ride in my little Toyota corolla. We laughed heartily many times about so many things. I hold dear all those memories of this wonderful human being. My condolences to you Pam and your children and their families.

Posted by Margarita Crowell - Brockton, MA - Coworker   August 01, 2017

Mrs. Fairfield, Our thoughts and prayers are with you, and your family, I worked with Win, at East Bridgewater, he was very professional in the workplace and a gentleman,, he will be greatly missed by everyone. Barbara and Ronald Putt

Posted by Barbara Putt - Friend   August 01, 2017


Rest in peace mr fairfield! You were an awsome principal and always there for your students we will always keep you in our memory and thoughts and prayers. RIP Lauren N.

Posted by Lauren Nelson - East Bridgewater, MA - Student   August 01, 2017

This is such heartbreaking news. Winston was the ultimate gentleman and the best vice principal any school system could ask for. He truly loved all the students and knew them all by name. I can still see him meeting the buses every morning and going to all three lunches. He had a wonderful sense of humor and fairness. He spoke often of his family and how proud he was of them all. My condolences to Pam, children and grandchildren. Maureen Hill

Posted by Maureen Hill - East Bridgewater, MA - Coworker   August 01, 2017