It is with heavy hearts that we announce the passing of Robert Hanson Whear, lovingly known as “Bobby,” on Jan. 17, 2025. Bobby left this world peacefully at Massachusetts General Hospital, surrounded by his devoted family, after a courageous two-month battle with leukemia. A cherished resident of both Marblehead, Mass., and Damariscotta, Bobby leaves behind a legacy of love, laughter, and extraordinary kindness.
Born on Feb. 24, 1954, Bobby grew up in Marblehead, where his passion for hockey first took root. He spent his childhood playing street and pond hockey and proudly represented the Bantam and town high school teams. His enthusiasm for the sport blossomed into a lifelong love, fueled by his admiration for the Boston Bruins and Bobby Orr. Bobby’s devotion extended to organizing many trips to the Frozen Four, being a part of the Hobey Baker Committee and collecting endless tales of hockey glory.
In Bobby’s mind, no one was a stranger. His charm, wit, and gift for storytelling made him the life of every gathering. His vibrant personality and fun-loving attitude took Bobby on many escapades and shaped his skills as an epic party organizer. He delighted in sharing memories, whether about the best local treasures or faraway adventures, spreading joy wherever he went. His zest for life took on new depth in the mid-1980s when he met the love of his life, Sherry.
Together, they embarked on their greatest adventure as co-innkeepers of the Mill Pond Inn, creating a haven of warmth and hospitality for over four decades, forming a multitude of so many amazing friendships worldwide that Bobby held very close to his heart.
During his marriage with Sherry he became a stepfather and friend to Marissa and Becky. He took them in and treated them and loved them as his own. Bobby’s heart expanded even more with the arrival of his beloved grandchildren – Troy, Dylan, Lilliana, and Antonio. Whether taking them on trips to Fernald’s for a sweet treat or simply filling their days with laughter and love, he was a grandfather in the truest sense – an unwavering source of adventure, wisdom, and boundless encouragement.
Bobby lived life to its fullest, juggling countless roles with boundless energy. In addition to building a thriving bed and breakfast, Bobby was a successful realtor, a Registered Maine Guide, a trusted board member of Great Salt Bay Sanitary District, an amazing bartender, and a cherished local figure. He has worked in the restaurant industry throughout his whole life and has spent the past two decades bartending at the Damariscotta River Grill. The patrons came on Thursday nights to hear his captivating stories and see his famous hockey puck collection. Bobby drew countless friends and admirers along the way.
His vibrant voice resonated across the airwaves on his rock-and-roll radio show and the local cable programs “Wuzzup” and “InnSannity.” Bobby’s written words also graced the pages of The Lincoln County News in his “Gone Fishin’” column, offering a unique perspective on life.
Among Bobby’s many achievements, most notable is his 41-year journey of sobriety. He inspired countless others through his unwavering dedication to recovery, offering guidance, hope, and steadfast support to both official and unofficial endeavors. His impact on the recovery community in Lincoln County and beyond is profound and enduring.
He leaves behind a family who will forever cherish his memory: his wife of 38 years, Sherry Whear; his daughters, Marissa and her husband, Chuck Deschenes, and Becky and her husband, Tony Freddo; his grandchildren, Troy, Dylan, Lilliana, and Antonio; his siblings, Debbie and Buddy Fox, Bruce and Heidi Whear, and Gary and Linnea Whear; along with many nieces, nephews, and a multitude of dear friends. Bobby was predeceased by his loving mother, Roberta; his father, Roger; and his sister, Diana Staples.
Bobby’s love, generosity, and larger-than-life spirit will forever be remembered by all who had the privilege of knowing him. He was a man who truly lived his life with open arms and an open heart, leaving a legacy of kindness and joy that will endure through the lives he touched. Rest in peace, Bobby. You will be deeply missed, but your light will continue to shine in the hearts of all who loved you.
In lieu of flowers we are asking for donations to be made in Bobby’s name to Hearty Roots, a nonprofit, outdoor-based youth development program guiding people off the grid and into their hearts. To learn more about this wonderful organization that was very close to Bobby’s heart, please check out their website and consider making a monetary donation in his name at heartyroots.org. Links for his scholarship program or “Bobby’s Camp” will be provided on the website.
Services will be announced at a later date.
To learn more about Bobby and his life, go to shorturl.at/nWjeU or read the “Characters of the County” feature about him at shorturl.at/3Mboe.
