Craig Stephen Pyy

In Loving Memory of Craig Stephen Pyy It is with heavy hearts that we announce the passing of Craig Stephen Pyy, a proud Coast Guard veteran, passionate outdoorsman, dedicated public servant, and beloved family man. Craig passed away peacefully, leaving behind a legacy of courage, adventure, and unwavering love for those around him. Craig served honorably in the United States Coast Guard for six years, embodying the values of service, discipline, and patriotism. His time in uniform was marked by a deep commitment to protecting others and serving his country with pride. For over 30 years, Craig worked for the City of Portland, where he began his career on the back of a trash truck. Through hard work, dedication, and an unmatched work ethic, he rose through the ranks to become the Coordinator of the Solid and Hazardous Waste Division, the position from which he eventually retired. Along the way, he earned the respect of his colleagues and built lifelong friendships, leaving a lasting impact on the city and those he worked with. A true outdoorsman, Craig found peace and purpose in the natural world. He had a deep love for hunting, and never missed an opening day of hunting season, a tradition he faithfully shared with his son. These mornings often began with the much-anticipated “Hunters’ Breakfast,” where Craig gathered with friends and fellow hunters to share food, laughter, and stories before heading into the woods. These traditions became sacred moments in his life and reflected his love for family, friendship, and the great outdoors. Craig was also a hobbyist race car driver, spending over a decade racing alongside his son—a passion they shared and cherished together. His love for the track wasn’t about trophies, but about adrenaline, teamwork, and making unforgettable memories. Craig’s life was forever changed when he met his life partner, Kathleen “Kathy” Densmore, aboard the Scotia Prince ferry. What began as a chance meeting on the water blossomed into a lifelong partnership filled with love, devotion, and joy. From that day on, Craig dedicated his heart and his life to Kathy, and together they built a life full of warmth, family, and shared traditions. One of their favorite shared joys was decorating their yard for the holidays—a tradition that brought delight not only to them but to their neighbors and community. Whether it was Halloween, Christmas, or the Fourth of July, Craig and Kathy poured heart and creativity into every display, turning their home into a cheerful landmark that made people smile. Craig was also known for hosting unforgettable parties for his friends and family—gatherings filled with laughter, music, and togetherness. No celebration was complete without his legendary fireworks shows, which lit up the night sky and became cherished moments for everyone who attended. He especially loved playing darts with family and friends—games full of laughter, storytelling, and friendly competition. Whether at the dartboard, in the woods, or under the stars, Craig made the most of every moment with the people he loved. Craig is survived by his loving mother, Diane Setler; his life partner of 37 years, Kathleen Densmore; his brother, Bryan Pyy; his sister and brother-in-law, Paula-Jean and Tim Condon; his step-brother, Jay Bartlebaugh; and his step-sister, Audrey Bartlebaugh. He was a proud father to Craig Stephen Pyy II and his partner Heather Trahan, Buzzi Densmore, Kandi Densmore and her partner Jeromy Stookey, and Kylee Densmore and her fiancé John Patenaude. Craig was a devoted grandfather to Keifer Tschopp, Brayden Smyth, Bryce Smyth, Brooklyn Pyy, Lucca Luciano, Aedan Pyy, Taylor Pyy, Craig Stephen Pyy III, and Tori Pyy. He leaves behind beloved nieces Michelle Doughty, Jeanelle Merrill-Pyy, Roxanne Smith and her husband Anthony, as well as other cherished nieces and nephews from across his extended family. Craig was preceded in death by his father, Roger Pyy and his wife, Marion; his stepfather, Bruce Setler; his brother, Christopher Pyy; Kathleen’s parents, Wallace and Priscilla Rogers; and Kathleen’s brother, Skip Rogers. Those who knew Craig will remember his adventurous spirit, generous heart, and deep love for his family and community. He lived with intensity, purpose, and integrity, and he leaves behind a legacy of warmth, tradition, and connection. A graveside service will be held at 11AM Saturday September 6, at Woodlawn Cemetery, Westbrook. Rest in peace, Craig Stephen Pyy. Your race is run, your darts are thrown, your fireworks have lit up the sky, and your holiday lights have shone brightly—but your spirit lives on in the hearts of all who loved you.

Craig Stephen Pyy

December 10, 1960 - August 29, 2025

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