Pauline Bertha (Simmons) Flagg

4 entries
  • "Rosalie, Roberta and families, My mother and I were very..."
    - Linda Travers
  • "Lovely lady, so sorry for your loss"
    - Jolene Smith
  • "Roberta and Rosalie, So sad to learn of Pauline's passing. ..."
    - Judy Million Williams
  • "Dear Roberta Rosalie and family, I was saddened to read of..."
    - Cathy Given
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Service Information
Roberts Funeral Home
62 Bowdoin Street
Winthrop, ME

WINTHROP - Pauline Bertha Simmons Flagg, 93, formerly of Winthrop, died Thursday March 14, 2019 at the Woodlands in Hallowell.

Pauline was born in Fayette, on July 7, 1925, the daughter of James and Ruth (Damren) Simmons of Winthrop. She was the widow of Robert Clifton Flagg, to whom she was married for 65 years, and lived in Winthrop most of her life.

Pauline had two daughters, Rosalie and husband, William Worthing Jr. of Manchester and Roberta Flagg of Augusta. Pauline had three grandchildren, William Worthing III and wife, Valerie of Manchester, Tammy Worthing Gregor and husband, Dale of Monmouth, Heidi Record and partner, Lindy Carroll of Wells. Pauline had three great-grandchildren, Amber Lynn Gregor of Monmouth, Jeffrey Worthing of Belgrade, and Rachelle Worthing of Sanford. She was blessed to have had a great-great-granddaughter, Baylee Worthing. Pauline sure did love spoiling her grandbabies. Pauline is survived by her brother, James Simmons and wife, Louise of Manchester and her sister, Shirley Hutchinson of Augusta.

Pauline walked three miles to the Winthrop Schools until she was a junior in high school. She married Robert Flagg at the age of sixteen. She was a member of the Winthrop Center Friends Church at the same time. She went to church most of her life, participated in the Thimble Club as well as worked on public suppers for community fundraising. She was a member of the Winthrop Grange for 50 years. She filled many leadership roles from creating programming, bringing flowers to the sick and comforting them. She also worked on the budget committee for the town of Winthrop. Pauline had her own cottage industry, making jewelry, painting wooden lawn ornaments, and helping elders with their homes. She worked in the shoe factory, was a sales clerk for Wilson's Dollar Store in Winthrop, chambermaid for the local motels, and an Avon representative, lastly, ending her career at K-mart in Augusta where she retired. In retirement years, she continued to work in her gardens and enjoyed the outdoors feeding the birds and visiting neighbors, family & friends. She also, had a passion for going to Boothbay and enjoying the sights. She will be deeply missed by all the hearts she touched over the last 93 years. Thank you, to all the staff at Woodlands in Hallowell for the care of Pauline over the last few years. A graveside service will be held in July.

Arrangements are in the care of Roberts Funeral Home, 62 Bowdoin Street, Winthrop. Memories, condolences, photos and videos may be shared with the family on the obituary page of our website at

In lieu of flowers donations can be made in memory of Pauline Flagg to:

Woodlands Assisted Living of Hallowell

152 Winthrop St.

Hallowell, ME 04347 or

P.O. Box 96011

Washington, D.C.


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Published in Central Maine on Mar. 15, 2019
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