Cheryl Helen (Rich) Bailey passed away peacefully in her home in Charlestown, NH on September 26, 2026.

Cheryl was born on March 11, 1950 to Stephen Rich and Helen (Odell) Rich in Worcester, MA.

She graduated from Longmeadow High School in Long Meadow, MA. Cheryl attended North Hampton Junior College in North Hampton, MA and Keene State College in Keene, NH.

Cheryl devoted 20 years, working as a drug and alcohol counselor at Seminole Point Hospital in Sunapee, NH. Afterwards, she worked in payroll at Whelen Engineering until she retired in 2012.

Cheryl loved the holidays! On Halloween, she was the trick-or-treater counter, usually having around 150 kids, but never running out of candy! She loved dressing up for Halloween as well and always changed out her decorations, based on the season and holiday of the time. These times brought her together with her family and extended family, which was one of her favorite ways to spend her time. She loved Fall and all the activities that would entail, leaf peeping, and apple picking with her loved ones. She also loved LOVE, becoming a Justice of the Peace later in life in order to marry couples that she knew, many of whom worked with her at Whelen. She enjoyed helping out in political offices, but never pushed her politics on family and friends, not even her husband! She was an avid reader and loved the ocean, reminding her of her time in the Cape and the mischievous adventures with her sister, Deb! Those adventures would ultimately include the introduction to the love of her life Robert.

Cheryl is survived by her husband of 53 years, Robert Bailey, and his ever expanding family. She leaves behind three sons and their spouses: Stephen (Amy) Bailey of Walpole, NH, Gabriel (Rebecca) Bailey of Charlestown, NH and Charles (Jennifer) Bailey of Mesa, Arizona. Grandchildren (and there are many!) include Kaitlan, Kelsey, River, Alexus, Isaac (Cheyanne), Hunter, Aidan, Jordan, Ava, Brady, Beckett, Maeve, Madden, and Sage and great grandchild, Logan. She also leaves behind her sister, Deb (John) Williams and nephews and niece: Scott, Casey & Courtney.

Visiting hours for Cheryl will take place at the Charlestown Memorial Chapel on Main Street in Charlestown, NH on Friday, October 2nd from 4 - 6 pm.

A Celebration of Life will be held the following day, Saturday, October 3rd, from 2 - 5 pm at Trapshire, located at 1434 Bellows Falls Road, Charlestown, NH.

In lieu of flowers, the family encourages you to make a donation to Janie’s Fund, as Cheryl was a fan of Stephen Tyler and has the pictures to prove it! Donations can be made at https://janiesfund.org/