Obituary: Robert D. Hastings III

July 22, 1948 ~ January 3, 2021

As a true titan of innovation and adventure, always off after his next big idea, Robert “Bob” Hastings led an interesting and diverse life.  

Janitor. Painter. Football player. Architect. Real Estate Developer. CEO. Magazine Publisher. Blues Festival Producer. The list of his varied professions is too long to list for one simple reason—Bob had an unyielding drive to always challenge himself. Push himself. Innovate. Create. Conquer.  

He never met a challenge he couldn’t rise above, and not just because of his lofty six foot seven frame. He looked at obstacles in his way as minor inconveniences, and always managed to find his way to the other side. However, once he was there, he didn’t stay long, his eyes already searching for his next goal. 

“Don’t get mad. Don’t get even. Get ahead.” This was something he often said to his two daughters, Anna and Kate. And he’d done just that himself. After a childhood in Cary, Illinois of being teased for his imposing height, he used that very same physique to dominate at football, earning him a place on the All-Conference team before then taking his spot as a defensive tackle on the Northern Illinois University football team. He rose to the top of the college football fray and was drafted by the Chicago Bears. A knee injury put an end to his career early, but in true Bob Hastings form, he quickly set his sights on a new goal. 

After flipping real estate in Illinois, Bob’s next big idea sent him on a path to Door County, Wisconsin. He would call this beautiful place home for the next twenty years, making lifelong friends and memories along the way… memories that included countless pranks that still induce laughter and stories anytime someone mentions his name. Just ask his friends to tell their favorite story, and they’ll keep you laughing for hours over the antics he got them all into. He loved spending Sundays boating to Chamber’s Island with friends and family and tending to the gardens at the eighty-acre farm he designed and helped build. The same place where he would raise his two girls with his first wife, Madeline, and spend almost fifteen years of his life. 

In 1990, Bob found his true passion when he took the position of the Executive Director of the Door County Chamber of Commerce. It allowed him to use his creativity to make his community a better place and help the small businesses inside of it thrive. He would spend his years in the position helping to grow Door County’s popularity as a top tourist destination while focusing on his ultimate goal of preserving its natural charms and beauty. 

After fulfilling all his dreams in Door County, including starting up Door County Magazine, Bob set his sights on a new horizon. It was then he met the love of his life, Donna Valler. The two of them embarked on a journey together that would eventually take them to the East coast where he took up his mantle as CEO of the Penobscot Bay Area Chamber of Commerce. Bob and Donna enjoyed their time on the beautiful coast of Maine, and Bob’s proudest accomplishments in his position were founding the Rockland Lobster Trap Christmas Tree and the Maine Lighthouse Museum. After seven successful years there, his restless nature for new challenges sent him and Donna on a new adventure where he would step into the position of the Executive Director of the Cape Ann Chamber of Commerce in Gloucester, Massachusetts. In this position he successfully marketed Cape Ann as “Massachusetts’ other Cape.” 

Bob and Donna enjoyed many happy years there, and in 2011 he decided it was time to retire. But retirement for Bob Hastings didn’t come in the form of kicking up his feet and relaxing. Instead, he embraced his deep love of blues music and his entrepreneurial skills to co-found the Gloucester Blues Festival with his friend and partner, Paul Benjamin. The event brought in world-class talent, and it still continues to thrive each summer.

In 2014 Bob and Donna decided to leave the frozen winters of the North for sunnier weather in Florida. He spent the last years of his life happily sitting in the sun with the love of his life by his side and his cherished pets in his lap until he parted this world on January 3, 2020 at the age of 72.

Gone but not forgotten certainly applies to Bob Hastings because he left his mark on so many people and places.

We’ll remember him every time spring arrives and we see the bright yellow daffodils carpeting Door County. It was his idea to plant over a million bulbs around the county, knowing they would multiply each year and give residents and visitors a colorful spring. And multiply they have, making our spring pop with the color and beauty he’d hoped for. Every spring he would ask his daughters to send him pictures of the flowers around town so he could enjoy seeing how his idea had flourished. 

We’ll remember him when we drive by the many buildings that wouldn’t be here without him, like the Country Walk Shops and the Church Hill Inn. It was his innovation that willed them into existence.

We’ll think of him when they light the Rockland Lobster Trap tree each Christmas and when visitors are welcomed to the Maine Lighthouse Museum.

We’ll smile when we hear the lyrical notes of the Blues, knowing he helped support the music he loved so much by creating the Gloucester Blues Festival. 

We’ll remember Bob Hastings in so many ways because he left his huge footprints everywhere he went. His two daughters and his two grandchildren will follow in those footsteps, as they each have the same inner tenacity and creative spirit he passed down to them. They will continue his legacy of creating their own paths and always remembering him as they strive to live a full and unique life that would make him proud. 

Robert Douglas Hastings III is preceded in death by his parents, Robert and Gloria, and his brother, David. He is survived by his wife Donna; daughter Anna (Jon) Calhoun; daughter Kate (Marty) Rispens; grandchildren Ava and Jackson Olson, Aliana, Nicholas, and Amelia Calhoun; sister Gail (Bill) Sutterlin; brother Thomas (Joyce) Hastings; sister Sarah (Mark) Sawyer; sister Elizabeth Junion.

At Bob’s request there will be no services held at this time. If anyone would like to make a remembrance in Bob’s name, please consider donating to the Blues Foundation or the Blues Musician Relief Fund at or to the charity of your choice.

Expressions of sympathy, memories, and photos of Robert may be shared with his family through his tribute pages at or