Ann Whimple Obituary

Ann Frances Chiaverini Whimple

January 29, 1970 - July 2, 2025

Ann Chiaverini Whimple passed away unexpectedly on July 2, 2025. Ann was born January 29, 1970, and grew up in Connecticut with her parents, sister and brother. She attended elementary and middle school in Haddam and graduated from Mercy High School.

After graduating from St. Joseph's College in 1992 with a degree in elementary education, Ann dedicated the next few years to raising her two daughters and running an in-home daycare before becoming a first grade teacher at Maplewood Annex School in Bridgeport, CT.

Ann had many passions in life. She loved horses. Her teen years in Higganum were filled with taking long rides on her beloved horse, Babe. She enjoyed 4-H camp, biking in the neighborhood, and family trips to Florida. As the oldest child, Ann looked after her younger siblings, which sometimes included a fist fight but always ended in a funny story that Tim and Michelle still laugh about when they reminisce.

From a young age and well into adulthood, Ann's creative outlet was dance. She always aspired to be a dancer and was the ringleader in choreographing performances with her siblings at family functions. She was also a gifted gymnast. Her talent, along with her gift for connecting with children, was recognized through opportunities to teach dance at local youth programs in Hamden, CT.

As a wife and mother, Ann added her special touch to family recipes of spaghetti sauce and meatballs, which were favorites. In true Italian fashion, there was always too much food, but it was just another way that Ann showed her love. Ann had a talent for making jewelry and spent hours designing and crafting unique pieces. She made special pieces as gifts for her husband and their wedding party. Her creations serve as a special reminder that she will always be with us in spirit.

When Ann met Jimmy, she found love again. They were married on January 24, 2021, surrounded by loved ones in a small beachside ceremony. They spent three years of marriage in Cocoa Beach, Florida, renting from Ann's dear friend Herman Safar, who loved Ann like a daughter. Ann and Jimmy spent their days walking on the beach, hanging out with friends at Jonathan's Pub, and enjoying the local flavor at Friday Fest in Cocoa Beach.

In May 2025, Ann and Jimmy realized their dream of relocating to Maine, where Ann could once again ride horses. They recently moved into a 100-year-old renovated farmhouse, where they were welcomed to the community by new neighbors who embraced them in friendship and support. Ann's goal was to build a barn and arena on the property to create a space to train therapy horses for disabled veterans. She felt that she lived in the most beautiful place in the world and was excited to enjoy every second of her new life.

Ann was small in size, but mighty when it came to her protective instinct. She'd be the first one to stand up to a bully, stand up for what's right, and stand up for those less fortunate than her. She'd go hungry before she'd let an animal starve. She was never afraid of fighting for the underdog, and she never forgot a friend. If you were lucky enough to be loved by Ann, you were always in her thoughts, even if you hadn't spoken in a lifetime.

Ann's life was not easy. Her path was beset with obstacles, which she navigated and overcame with the support of her friends and her faith. She cherished the memories she had with her family, the bonds she had with animals. We are comforted knowing she is at peace, and happy to have memories of her big smile, infectious laugh, generous soul, and ability to love.

Ann is survived by her husband Jimmy, her daughter, Cassandra Brereton, son-in-law Max, their daughter Brooke, and daughter Jessica Carangelo, her partner Alex and daughter Alice. She is also survived by her mother, Carol Chiaverini, her sister Michelle Piccerillo and fiance Mike Papale, her brother Tim Chiaverini and wife Lara, several nephews, James, Elias, and Nico Chiaverini, Jon, Ryan, and niece Samantha Piccerillo. Ann was predeceased in death by her beloved father James Chiaverini and her dear friend Scottie Labanero. Ann and Jim's pets Sarge, Sabot, and Lady Kraken survive her.

Relatives and friends are invited to call 10:00 AM Monday, July 14, 2025, at Lancaster-Morgan Funeral Home, 11 Clover St., Caribou, ME 04736, where a service will be conducted with family friend, Troy McCrum officiating. Interment will take place at Maine Veterans Cemetery in Caribou.

In lieu of flowers, please make a donation to Wounded Warrior Project, woundedwarriorproject.org or choose a special spot and plant a tree in her memory. Arrangements in care of Lancaster-Morgan Funeral Home. Memories and condolences may be shared with the family at: www.lancastermorgan.com