Diane L. Josephson

Diane Leslie (Chickosky) Josephson, 59, loving wife of 22 years to Scott R. Josephson of Enfield, Connecticut, passed away quietly on September 22, 2025 after a long illness, with her devoted husband by her side. Diane was born July 5th, 1966 to Theodore J. and Marion L. Chickosky of Enfield, CT. Diane was a 1984 graduate of Enrico Fermi High School in Enfield and had a decades long successful career in the insurance industry serving in the Medical Claims and Underwriting service areas.

Diane lived life with vim and vigor and had a subtle talent for meeting new people through casual conversation. She had an incomparable heart of gold and was charitable to no end. Her boundless generosity was often demonstrated by the gifts she would send unannounced or unexpectedly and accompanied by the most love, affection and friendship a person could offer. And, she loved donating to the local food shelter during the holiday seasons. She loved day joy rides, glamping in VT, beach day trips as well as beach vacations to Hampton Beach. She had a passion for flowers and often loved planting and arranging them in her yard along with her many farm animal ornaments that could be seen throughout her yard all year long. She especially loved watching cooking shows, listening to Zydeco music, her favorite band Journey and Joe Cocker. She loved talking about her younger days shopping at Grants with her Granny Lange often recalled when hearing the song Reminiscing by the Little River Band. But most of all, she enjoyed spending time at her parents catching cool breezes in their driveway during hot summer days, winter holidays at their house or traveling with her mom and family to local craft fairs and flea markets.

Besides her husband, Diane is survived by her step-daughters Brittany and Erica Josephson, her twin sister Denise Cimadon and husband Marc, her brother Brian Chickosky, wife Rainelle Mckenna and nephew Nicholas Chickosky. She is also survived by her Uncle Ron Chickosky and his wife Darlene, Aunt Joan Burgess and family, her besties Deanna Shepard, Goldie Stears, Donna Deschenes and many more family and friends. Diane was recently predeceased by her mother, father, Aunt Doris Sullivan and her long-time beloved cat Mr. Kitty.

Diane's family will receive relatives and friends from 1PM to 3PM on Saturday, September 27, 2025 at Leete-Stevens Enfield Chapels, 61 South Rd, Enfield. A funeral service will immediately follow the visitation. Burial will be held at a later date. For online condolences, please visit www.leetestevens.com.

In lieu of flowers donations can be made in her name to the Connecticut Cat Connection Adoption Center, 40 Stevens Mill Rd.. Windsor, CT 06095 or at www.CTCatConnection.org.