WOLFEBORO — A small local business with a big heart is looking for a new owner. Kathy Fairman, present owner of the Wolfeboro Trolley Company, has confirmed the Molly the Trolley business is for sale.
“It’s been a privilege to work with local businesses in this group effort to attract and introduce visitors to our town,” she said. “However, after 38 years, it’s time for me to step aside and make room for someone else to lead this effort. I’m confident that they will enjoy working with Molly and our community as much as I have.”
In addition to offering narrated tours, Molly the Trolley accepts charters for private events such as weddings, dinner parties and concerts, a service that is also an important source of Molly’s income.
“The charter business developed because there was a need for safe, reliable group transportation,” said Fairman. “And no one makes that more fun and festive than Molly.”
“However, the greatest reward for me has always been the joy and smiles on the faces of the little ones,” she added. “When children watch Molly go by, or when they climb aboard, I see magic in their eyes, and there’s nothing better than that.”
Molly the Trolley was brought to town in 1987 by three local business owners — Gregg Roark Sr. (Wolfeboro Casuals), Richard “Dick” Eaton, Sr. (The Laker), and David Hemenway (Black’s Paper Shop) in hopes of easing traffic congestion downtown.
While Molly proved popular as a fun ride, people did not use it in lieu of parking downtown, so Eaton and then business partner Kathy Fairman (The Laker) established the Wolfeboro Trolley Company, Inc. and made Molly an attraction with narrated tours.
“I believe it’s been successful in that role,” said Fairman. “Businesses support Molly by purchasing signs on the trolley and/or ads in her Map/Brochure, and many have continued to do so for decades, some like Bailey’s and The Art Place, since we started. I have to think they keep coming back because they also believe Molly the Trolley is good for business in Wolfeboro.”
Fairman is firm in her plans to step down as an owner and driver this year.
“I made this decision two years ago and I’m going to hold myself to it,” she said. “It has been a gradual process. Molly has an experienced staff including a manager ready to take the reins under new leadership. She will be ready to roll in the spring, but it won’t be with me as owner.”
Acknowledging that a public announcement of her intention to sell is a bit unusual, Fairman explained that while she hopes Molly the Trolley will continue in Wolfeboro, she knows that may not work out.
“I want people to know now that this is happening,” she said. “What I don’t want is for someone to come forward after the trolley is gone and say, ‘If only I had known..’ “
For more information, contact Fairman directly at 603-569-1080 or info@wolfeborotrolley.com.


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