Column: A cheer for Penny Wig

Courtesy photoPenny Wiggleworth leading the Oldies But Goodies.

Penny Wigglesworth, a native Marbleheader who passed away in Naples, Florida, at the end of May, was a bright spirit who added a spark of life and love to just about everything she touched. Her specialty was “cheer.” She seemed to constantly find new ways to “cheer” — whether it was to “cheer on” (praise, encourage and support people), “cheer up” (comfort, uplift spirits and ease concerns of people, or just plain make people feel good about themselves and life in general.

As a fresh-faced Marblehead High cheerleader in the ‘50s, Penny Clarke energized the team, sparked the crowd and sweetened the dreams of gawking gangly boys.

In 1960, Penny married another bright spirit, the outstanding Giff Wigglesworth, and together they “cheered” the world with four go-get-’em kids: Nancy, Giffy, Sally and John.

In 1973, Penny Wig (as she was fondly known to her kajillion-and-a-half friends) was named the first-ever national sales manager for Harbor Sweets, located in Salem, a highly regarded purveyor of handmade chocolate delectables. (Needless to say, access to these treats was another form of cheer she could — and did — share.)

She was an excellent skier, tennis player and golfer. In 1984, at Ferncroft Country Club, surprised by the sound of a distant cheer, Penny learned that she’d oh-by-the-way aced herself a hole-in-one. Husband Giff was surprised, too — he later got one of his own.

In 1986, the Marblehead Gridiron Club named her grand marshal of the Homecoming Day parade, which was led off by Penny and her Oldies But Goodies cheerleader pals from the ‘50s — the parade and the Goodies were Penny’s idea. The Gridiron Club plaque thanked her “for inspiring renewed spirit in our team, our school and our community.”

The pivotal, life-changing event, ultimately responsible for the free-flow of charitable cheer that continues to this day, occurred in 1994 when Penny was stung by a bee, went into anaphylactic shock, and had a near-death experience. As she compellingly describes it in a 2016 video available on YouTube, it was an amazingly positive experience that made her no longer fear death, and also made her realize she was “in a different place now.”

In 1995, the volcano erupted. The desire “to help people” which had been welling up inside Penny as long as she could remember could no longer be contained. She founded the Penny Bear Company. Her Penny Bear mission statement: “A safe, welcoming community of people who would come together to provide comfort to others” scarcely touches the surface of the diversity of ways this wonderful organization would bring cheer to countless thousands of Penny’s “heroes” — the hurting, the helpless, the forsaken, the frightened — in the course of the next quarter century.

Today, Penny Bear Company, a frequent recipient of local, regional and national honors for excellence in its many charitable endeavors, is an all-volunteer nonprofit providing outreach, gifts and messages of hope, comfort and emotional support to an endless list of organizations — hospitals, hospices, assisted living facilities, nursing homes, camps for critically ill kids, service and charitable institutions.

(Penny’s daughter, Sally W. Cioffi, can fill you in on the Penny Bear organization itself, and/or how you might be of help. Sally can be reached c/o The Penny Bear Company, 6 Elmwood Road, Marblehead, Mass., 01945; by phone at 781-631-5988; or emailed at The website is

It’s only appropriate to close with an expression of tribute and gratitude to the most sparkling, gracious and irrepressible cheerleader of them all in the form of a very simple but heartfelt cheer: Yay Penny Wig!

Bob Baker lives in Marblehead.


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