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Doris Osgood and Phyllis Shaw: Sisters at Wayside Pines


Doris Osgood and Phyllis Shaw are sisters from the Libby family in Bridgton. At a young age they worked with their mother doing laundry for the summer camps in western Maine. “Washing clothes is the only thing we know how to do,” they chuckle. At 18 they graduated from Bridgton High in a class of less than 50 students and almost none of them were male. “That’s because most of the boys enlisted before graduation.” When WWII ended, the men came back and Doris and Phyllis both met their respective husbands shortly after. Their weddings were only a few months apart. “I met John at the legion hall dance. They had one every Friday night where the new community center is now,” recalls Doris.

While Doris moved one town over to Denmark with her husband to work at the Cardinal Printing Shop, Phyllis remained in Sandy Creek and worked at the Red and White Grocery (which is now the large Reny’s on the main drag). This would be the farthest distance they would ever live apart from each other as they raised families and spent roughly half a century with their husbands and children.

Their lives mirrored each other yet again when both their husbands passed away within a year of each other, leaving Doris alone in the home she and her husband owned and Phyllis alone in Sandy Creek in her trailer. In their 70’s at the time, the Libby sisters applied for subsidized housing. Thinking back on that time Doris lists all the maintenance her house needed, and how little of it she could do herself. “I couldn’t maintain the upkeep. My son told me after I moved here it was the best move I ever made.”

While Doris only had to wait one year for her apartment (which she moved into in 2000), Phyllis spent three years on her own in her trailer before she was able to move in 2002. Now the two sisters live across the courtyard from each other at Wayside Pines in the very same town they were born and have found a welcoming home.  Barbara, whose story was told and posted a few weeks back, is Doris’s best friend. They visit each other daily and are avid advocates for their community’s wellbeing; communicating with their resident service coordinator frequently to ensure that Wayside Pines remains safe and continues to serve its residents.

Doris Osgood and Phyllis Libby
Residents, Wayside Pines

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Check out Avesta's blog, The Porch Light, for more news, updates and stories.

Contact Development and Communications Manager Sara Olson at 207-553-7780 x3352 or by email.