Brian R. Bailey

Brian R. Bailey, 52, of Pittsfield, passed away at home in the early morning hours of Friday, July
2, 2021 after a long and tiring battle against glioblastoma. He was a beloved father, husband,
brother, son, uncle, and friend.

Son of the late Gordon and Marguerite Lyman Bailey, he grew up in Dalton and graduated from
Wahconah Regional High School in 1986. Brian was quick-witted, always good for a clever,
groan-inducing pun or Dad joke, and full of Monty Python quotes. He could whistle like nobody’s
business, loved a good crossword puzzle, and was a walking encyclopedia of music trivia.
Brian was well known for his artistic ability, and left behind a large collection of his character
sketches on napkins and scraps of paper, at his workplaces, bars, coffeehouses and friends’
homes all over Berkshire County. He had a unique style that could be easily recognized, even
as it evolved throughout the years.

Also well-known was his love of music. He had many adventures following the Grateful Dead
and attending local music shows, where he could be found dancing and smiling. Through his
love of music he bonded with many and created several lifelong friendships. Brian’s taste in
music was eclectic, and he loved sharing it with friends through “mixes” that he spent many
hours curating. One of his favorite things was to conduct “music lessons” in which he would
introduce his children to a band or musician that had influenced his musical tastes. He made
sure Phoebe and Phin grew up appreciating everything from the Beatles to the Beastie Boys.
Brian had a natural ability to connect with others, which suited him well in his chosen profession
of mental health care worker. He was able to meet people where they were and help them find
ways to make their lives better. He was a gifted caregiver and loved the people he was
privileged to help. He made many friends through his positions at Hillcrest, the Brien Center,
and Berkshire Service Group.

Brian leaves behind his loving family who miss him so much: his partner of 26 years, Catherine
Fennelly, with whom he celebrated 20 years of marriage last September, and his two children,
Phoebe and Phineas. They were everything to him. Being a father was not just a title to Brian, it
was an adventure, and one he relished. He also leaves behind his brothers, Thomas and Jeffrey
(Jen), his in-laws Bill and Marilyn Fennelly, brother-in-law Parker Fennelly, nephews Ethan
Fennelly and Jonathan Bailey, and his uncle, Philip Bukowski. He also leaves behind a legacy of
love. He encouraged everyone around him to remember that ALL YOU NEED IS LOVE. In his
memory remember to be kind, respect one another, and love fiercely, because our time here is
short and precious.

The family would like to thank everyone at HospiceCare in the Berkshires for their loving care.
We also couldn’t have made it through this journey as long as we did without the help of the
staff at BMC, Berkshire VNA, and the BMC Cancer Center. We also want to thank everyone at
Berkshire Service Group and Your Color Connection, as well as friends and family who reached
out, for all your love and support.

Per Brian’s wishes, there will be no calling hours. A memorial is being planned for early August.
Anyone wishing to make a donation to the family can do so by going to or by sending it to Catherine Fennelly c/o Your Color Connection,
36 Pittsfield Rd, Lenox, MA 01240.


Let the family know you care by sharing this tribute.

17 Condolences

  1. Lisa Roberge on July 8, 2021 at 7:11 pm

    Brian was quite possibly the kindest person I ever had the privilege of knowing and I consider myself incredibly lucky to have been friends with him for so many years. He exuded joy in all adventures. He is missed.

  2. Jennifer Humphrey on July 8, 2021 at 7:27 pm

    I never knew Brian, but I felt his kindness and large heart through his friendship with my husband, Steve. May he be at peace.

  3. Josie Herzog on July 8, 2021 at 7:29 pm

    So very sorry I the loss. R.I.P. Brian fly with the angels

  4. Angela Gajda on July 8, 2021 at 7:29 pm

    I never saw Brian without a smile on his face. Even when he was at Target getting some crazy Spiderman Pig, Phin asked for for his birthday. We laughed because by putting it off he got it on sale.
    He will be missed by so many. His art work is proudly hanging on my refrigerator.
    We are lucky to have known him.

  5. Carol R on July 8, 2021 at 8:15 pm

    Brian was very helpful to me…kind and witty. May he restbin peacee….

  6. Rachel Alemany on July 8, 2021 at 8:44 pm

    So many memories of Brian through HIllcrest, Softball, Tor concerts, Bucksteep and so many more. My favorite memories are the times I would run into him at Herberg for Parent/Teacher nights and he would just glow being with you and the kids. His memory is for a blessing. Brian was a blessing.

  7. Rebecca walsh on July 8, 2021 at 9:09 pm

    How beautiful it was to see the kindest sweetest man meet the kindest sweetest woman. Your love inspired us all and reminded us each day of what was important. God bless each of you. See you on the other side Brian.

  8. Cara Petricca on July 8, 2021 at 9:38 pm

    Brian and I met 30+ years ago at Bucksteep when I saw him drawing a sunflower child in overalls on a napkin. He was kind enough to give me a ride back to Pittsfield after my Jeep wouldn’t start. This started a lifelong friendship based on Art, Music and Laughter as well as a mutual collection of odd friends. I remember Brian showing up out of the blue at my apartment in CA with a gaggle of Dead followers – we could always pick up right where we left off, always meandering dear friends. I’ll miss our laughs and always be grateful for the gift of feeling like a part of his beautiful family in my own introverted way. Thank you Brian for all the years of friendship. My love is with your Catherine, Phoebe, and Phinny now and forever.

  9. John Lyford on July 8, 2021 at 9:45 pm

    I am deeply saddened by the loss of Brian. He had many wonderful facets in his personality. I especially miss his brilliant caricatures and cartoons, created with just enough whimsy to diffuse the most exacting critic. I rue what might have been with this talent, had he stayed with us. I also saw a deeply devoted family man, a role model for any father and husband. My thoughts and prayers are with those he loved that remain.

  10. Tracy Delsignore on July 9, 2021 at 2:53 am

    I first met Brian Bailey at Lenix coffeehouse where he was a regular and I was too. Conversations lead to music, my children’s children were the same age as his children and he became part of our little community. Brian and I started sharing mixes which I have to tell you was the best medicine for what was ailing me at the time. I was nursing a broken heart and randomly A mix would show up in my mailbox, I knew it wasn’t specific to me but they were so well curated and so thoughtfully recorded that they got me through one of my most difficult journeys. As time progressed I saw less of brian only due to Changes work life and in daily circumstance. His wife Catherine and two children are an incredible legacy he has left behind. I will always be moved by his kindness, his sincerity, his undying love for life and his laugh. To Catherine and the children there’s a community of folks that are holding space for you. May he Rest In Peace And may your memories and his love comfort you always

  11. Marian Harris on July 9, 2021 at 2:03 pm

    1st met Brian through work. He also had a sense of humor and was very caring in helping people out. Always kept in contact with him, enjoying his art, and words. Miss him so much and sending hugs to his family❤️

  12. Fred Vradenburg on July 9, 2021 at 6:57 pm

    Worked many hours with Brian at Pomeroy. He always made the time go by fast and was always very compassionate with the Clients. Rest in Peace my friend.

  13. Lysa Ranti on July 9, 2021 at 11:46 pm

    So sorry for your loss. I’ve known Brian since high school and loved seeing him out and about at local music venues where we would always catch up over a few drinks and play darts together. He was such a humble soul. He will definitely be missed. Rock on Brian, fly high with Angels.

  14. Marie Regnier on July 10, 2021 at 3:56 pm

    To Brian family, I had the pleasure to work with Brian at Berkshire Service Group and will remember him for his humor and engaging personality. He will be missed Marie Regnier

  15. Susie Phoenix on July 10, 2021 at 5:59 pm

    How could anyone not love Brian? (And Catherine, Phoebe and Phineas.)
    When I worked in Lee it was always a highlight of my day when Brian stopped by to see Catherine. Or when Phoebe played with the toys in my office.
    He is/was my friend; a deep, loving, fun-loving, magnificent human being who found glory in loving connection and fascination with life. You are gone too soon, dear Brian. So happy for the 52 years you were here.

  16. joan smith on July 15, 2021 at 2:22 pm

    Brian was one of the beautiful people making everyone around him feel good. He had one of those charismatic smiles that seemed to last forever. Brian´s artistic abilities were distinguishable. He will be dearly missed. My thoughts and prayers are with his family.

  17. Elizabeth Frank Elsbeth on July 17, 2021 at 1:19 am

    We were just a ragtag group of adult kids when we met as a bunch of 1992 hippies in Lenox and were chilling at BPAC and Tanglewood. Brian was the epitome of kindness, peaceable living and love for all.
    He, well. He. He lived. He loved and was loved.
    A more authentic soul and steward for all the hope in humanity – yall wont meet his equal except in his children and the legacy he and Catherine built/d in his name.
    Rest easy friend.
    Fly free.

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