By Kevin Greer
Lakeside Communications Manager
Tom Henderson is a familiar face to many Lakesiders. For more than two decades, he has welcomed guests as one of the friendly shuttle drivers, steering the large golf carts with orange flags and offering rides across the community.
When Henderson turned in his golf cart key at the end of the 2025 season, it was for the last time. After 23 years, 19 of them as a supervisor, he retired from the role that helped thousands of people reach their Lakeside destinations.
“I talked about retirement for a couple years,” Henderson said. “Finally, I decided this year was going to be it. The timing was right.”
Henderson, born and raised in Coshocton, Ohio, first came to the Marblehead Peninsula in 1991 after purchasing a sailboat. Four years later, his family bought a cottage, and his wife and daughter opened a gift shop on Bayshore Road. He helped at the shop during summers and became a full-time resident after retiring as a junior-senior auto mechanics teacher.
Even in retirement, Henderson stayed busy. He continued helping at the shop and served as a court-appointed special advocate for abused and neglected children through the Ottawa County Juvenile Court. Then, a new opportunity came his way.
A friend, “who is always looking to make a buck,” told Henderson he had already lined up jobs for both of them as Lakeside shuttle drivers.
“He told me, ‘We’re going to be hauling people around Lakeside on a golf cart, and you’re already hired. You just have to fill out the application,'” Henderson recalled. “I didn’t know what it was, but I thought, ‘Well, I’ll give it a try.’”
After four years, Henderson and fellow driver Jim Heikes were promoted to co-supervisors. When Heikes retired in 2017, then-Director of Guest Services Mary Ann Hirsch asked Henderson who he wanted as his new co-supervisor. Henderson chose to lead on his own, a role he carried out successfully for the next eight years.
As supervisor, Henderson managed hiring, scheduling, daily operations and cart maintenance. He oversaw a staff of 15 drivers, mostly retirees from diverse backgrounds, including pilots, bankers, teachers and lawyers. With little turnover, the team became like family.
“They were all friends, willing to jump in and cover each other’s shifts if needed,” Henderson said. “It was just a great group to work with.”
Although the job often looked fun, Henderson said it came with challenges. Drivers worked long hours in rain and heat, without the comfort of air conditioning.
“Spending eight hours on a golf cart is not as easy as you think,” he said. “It takes a toll, especially on rough streets and really hot days. There were times I got home completely drained.”
The shuttle team also went above and beyond for Lakesiders who need extra assistance. Henderson once picked up a blind woman from the Lakeside Salon & Spa, helped her into her cottage, retrieved her keys, and even checked her air conditioner. Another driver took a blind person to the grocery store after hours.
“We do more than just drive,” Henderson said. “We do all kinds of things for people in Lakeside.”
Henderson earned deep respect from both his staff and his colleagues.
“Tom was a great colleague and is a great friend,” Hirsch said. “He was very dedicated to his job, but most importantly, to his fellow colleagues and me. It was a pleasure working with him.”
Current Director of Guest Services Steve Koenig added, “Tom created a positive, fun culture that always had a fair amount of humor. There was never a worry or a concern about what the shuttles were doing, because they were in very capable hands with Tom. That’s something that is easy to take for granted. I’m going to absolutely miss him.”
Retirement will not slow Henderson down. He is a trustee at the Lakeside United Methodist Church, president-elect of the Marblehead Peninsula Lions Club, and will also be working part-time at Millie Magoo’s & The Fine Print, owned by former shuttle driver Traci Richards. He even helped her with carpentry and painting before the store opened in May.
“We became extremely close friends,” Henderson said. “When she asked me to work at the bookstore, I thought it would be neat thing to do. I used to be her boss. Now she’s mine.”
Looking back, Henderson is grateful for his time working at Lakeside.
“I’m just appreciative of the support I’ve had over the years from the administration and the residents,” he shared. “I’ve said it every year that I had the best staff in Lakeside. They’re just great people.”
