Penny Clarke Wigglesworth


Penny Clarke Wigglesworth, of Naples, Fla., formerly of Marblehead, born on Dec. 29, 1938, passed away on May 30, 2020, at the Avow Hospice House in Naples. She transitioned to “a place of pure love,” into the awaiting arms of her late parents Charlotte (Rogers) and John Allen (“Jack”) Clarke, and her late husband of 41 amazing years, Giff Wigglesworth Jr. She also joins her sisters, Kimball Clarke Brooks and Carolyn Rogers Antonik. 

Penny was extremely proud of being the first national sales manager for Harbor Sweets. Her next big accomplishment was the creation of the Penny Bear Co., a safe, welcoming community of people who would come together to provide comfort to others in need of a “hug.” The Penny Bear hugs reached so many people’s hearts near and far; from homes, hospitals, and into schools, “Life Is Good” Hunter bears, “Slow down for Allie” bears, to donations of bears, books, and calendars to various organizations, hospices, Paul Newman’s Camp, Haiti Hurricane relief, Shriners Hospital, and so many more. When Penny went to Naples in the winters, she brought her workshop and book clubs with her, which also extended to friends in Roanoke, Va. Of course, she didn’t stop with just the Penny Bear workshop. She extended her arms and opened her home to support groups and healing activities. One of the support groups was for those living with Parkinson’s, which Penny ended up struggling with for the past 10-plus years. Parkinson’s finally took its toll, as Penny went on to her next chapter, peacefully holding her children’s hands, with a Penny Bear in her arms. 

Mom said on one of her last days with us that she was so lucky to have had such a great life, to have met so many special people, and to have such a wonderful family. We were the lucky ones to have had her as our Mom, Grammy, Aunt, and friend: Nancy Wigglesworth Dugan (Dion) of Vineyard Haven and Brewster, Giff Wigglesworth III (Sue) of Marblehead, Sally Wigglesworth Cioffi (Doug) of Marblehead, John Clarke Wigglesworth (Stacey) of Sacramento, Calif.; Lt. Johnathan (U.S. Navy) and Thomas Dugan, James, Chris, and Nick Wigglesworth, Drew, Sam, Ford, and Alexa Cioffi, Abby and Reese Wigglesworth, along with her nieces and nephews (Rogers, Brooks, and Caldwells); her extended family, and many many friends; as well as all of the lives she touched through her support, caring, and hugs with her Penny Bear Co.

Donations in Penny’s memory can be made to your local hospice, Avow Hospice in Naples, the Michael J. Fox Foundation, or the Penny Bear Co., 6 Elmwood Rd., Marblehead, MA 01945; or as simply as just giving someone a hug who needs it! 

A celebration of Penny’s life will be held at 2 pm on Sunday, Oct. 4, at Tedesco Country Club (any COVID-19 precautions at that time will be determined and posted closer to the date). Arrangements are under care of Legacy Options Funeral & Cremation Services, Naples.