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521 West Main St
Phone: (413) 663-6523
Jessica Cutler

Jessica Lynn Cutler (Passetto)

Monday, September 22nd, 1986 - Friday, April 3rd, 2020
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Jessica Lynn Passetto Cutler, 33, of 92 Northumberland Road in Pittsfield, beloved wife, mother, daughter, educator, and performer, died suddenly and unexpectedly on Friday, April 3rd, 2020 at Berkshire Medical Center in Pittsfield.
Born in Pittsfield on September 22nd, 1986 to Joseph Passetto and the late Michelle-Rene Mack, Jessica grew up in Hinsdale and was educated at Kittredge Elementary School, Nessacus Middle School, and was a 2005 graduate of Wahconah Regional High School, where she excelled as a student and participated in the music and drama programs.
Continuing her education, Jessica attended Massachusetts College of Liberal Arts in North Adams, graduating in 2009 with bachelor’s degrees in Education and Sociology. Jessica received her master’s degree in Education from American International College in Springfield in 2016, graduating with a perfect 4.0 grade point average.
Jessica was devoted to her career as an educator and loved helping young children brighten their future. While completing her studies, Jessica worked at Craneville Elementary School in Dalton as a paraprofessional and substitute teacher. Jessica then began her career as a classroom teacher in 2011 teaching sixth grade at the former Cheshire Elementary School. In 2012, Jessica was hired at Hancock Elementary School, and in her four years there, she would teach 3rd, 4th, and 5th grades and music education.
In 2016, Jessica was hired by the Pittsfield Public Schools and taught 3rd grade for one year at Morningside Community School. In 2017, Jessica transferred to Allendale Elementary School, where she became a beloved member of the school community while serving as an academic interventionist, assisting students in enriching their reading and math skills. For the last two years, Jessica split her time between Allendale and Williams Elementary Schools and would often give time after school for drama productions and would tutor students on band instruments.
During the summer months, Jessica was employed by the Boys and Girls Club of the Berkshires, working at Camp Russell in Richmond, and served as the director of the summer Brain Gain program, which received several local and national accolades for its’ effectiveness in furthering educational development.
Jessica was an extremely talented musician and performer. Since 2000, Jessica played tenor saxophone and clarinet in the Eagles Band wind and big band ensembles, rarely missing a rehearsal or performance in 20 years. Jessica often lent her talents for local performances for charitable causes, including annual Yule for Fuel performances for the Pittsfield Area Council of Congregations fuel assistance program. Jessica also sang in the soprano section of the Berkshire Concert Choir and was a member of Temple Anshe Amunim’s adult volunteer choir. In 2013 and 2014, Jessica was a top 8 finalist in the Berkshire Idol singing competition.
On June 1st, 2012, Jessica met Joshua Cutler while singing karaoke at the former Coyote Den restaurant in Lanesboro. Their friendship quickly blossomed into a relationship, and on August 6, 2016, Josh and Jessica were married at Temple Anshe Amunim in Pittsfield. Josh and Jessica shared a deeply loving relationship, delighting together in going out to dinner, their annual summer visits to Cape Cod, nights on the lawn at Tanglewood and at Pittsfield Suns games at Wahconah Park, trips to Fenway Park to see the Red Sox, performances together with the Eagles Band, and nights playing music together while sitting on their front porch at home.
On February 18th, 2020, Jessica achieved her greatest life goal, becoming a mother to James Thomas “JT” Cutler, named after James Taylor, Josh’s favorite singer. Though her time with her son was far, far too short, Jessica showed in her six and a half weeks as a mother the incredible and unconditional love and bond that a mother and child share.
Jessica was a member of Temple Anshe Amunim in Pittsfield, where Josh currently serves at the congregation’s president. Jessica was extremely active in Temple life, serving on the Feigenbaum Lecture and Membership committees, helping with the Hebrew school, and was a participant in Hebrew learning classes.
Jessica enjoyed spending time with friends, swimming, attending live music performances, listening to Billy Joel, Sudoku, Snoopy and the Peanuts, baking and decorating cakes, holiday celebrations with family, and doing things to make other people happy and feel good about themselves, whether it be a small gift or a note of encouragement.
Besides her beloved husband and son, Jessica leaves behind her father and stepmother, Joseph and Colleen Passetto of Hinsdale; her brother, Timothy Passetto of Brookline; her sister, Amber Passetto of Hinsdale; her mother-in-law, Ellen Cutler, of Pittsfield; her brother-in-law and sister-in-law, Zachary and Julie Cutler of Pittsfield; and many close aunts, uncles, and cousins, and so many dear friends who loved her.
Jessica was predeceased by her beloved grandmother, Berna Passetto, who died on April 26th, 2015, and by her father-in-law, Dr. Alan Cutler, who died on March 4th, 2020.
FUNERAL NOTICE: Due to the Coronavirus and social distancing recommendations, a public memorial service to honor Jessica and her beautiful life will be held at a date to be announced. Burial will be private and at the convenience of her family. In lieu of flowers or memorial donations, the Cutler and Passetto families have established the James Thomas Cutler Education Fund, which will one day help James achieve Jessica’s dream of her son attending college and continuing to further his education. Contributions to the fund can be made in care of the funeral home. FLYNN & DAGNOLI-BENCIVENGA FUNERAL HOME, 5 Elm Street, Pittsfield, has been entrusted with arrangements. To add to the Book of Memories, please visit
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Service Details

  • Interment

    Pittsfield Cemetery Crematory
    203 Wahconah St.
    PITTSFIELD, MA 01201
    Get Directions: View Map | Text | Email
A public memorial service will be at a later date at a time to be announced.


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Olivia Oleskiewicz

Posted at 11:03am
Mrs. Cutler was a really nice teacher, and she helped me with a lot of my math and I really miss her

Love: Olivia Oleskiewicz

John McHugh

Posted at 05:14pm
Josh & Family So sorry for your loss, our deepest condolences. John & Cathie McHugh

Cara Adornetto

Posted at 07:50pm
I'm wishing comfort and healing to your family and the community for all she has done.. This tree is for her and her family.
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A memorial tree was planted in the memory of Jessica Cutler — Plant a Tree Now

Ruth Franchere-Melbourne

Posted at 08:22pm
Jess, I will always remember your smiles and quick wit, but especially your laughter and kind heart! It has been a pleasure playing with you in the Eagles Band, and will miss you very much! May God bless and keep you, and may He also comfort and guide Josh and James through their time of grieving! Amen! Josh, both Tim and I are very sad to hear of Jess’ passing! We extend our condolences to you and James, and pray that you will be okay! - Ruth Melbourne & Tim Franchere

Jane Hanson Wallace

Posted at 02:53pm
Dear Josh and family We were so upset to hear of Jess's passing. Words can not begin to describe our sad we all are. Jess was so excited about getting pregnant and finally becoming a Mom.She was so great with the kids at Allendale. She would be walking down the hall with that beautiful smile and always something wonderful to say. Please know our prayers and thoughts are with you all . Dave.Jane, Kevin,and Mary Wallace

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