Wolfeboro Trolley Company

05/29/2026

05/24/2026

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05/18/2026

We want to extend our deepest thanks to Kathy Fairman for founding the Wolfeboro Trolley Company and building it into such a true pillar of our community over the years.

Her dedication, hard work, and unwavering commitment to the company’s success, especially throughout this ownership transition period has been monumental and so deeply appreciated.

Kathy’s passion and leadership have touched countless lives, and the impact she has made in Wolfeboro will continue for years to come. We are incredibly grateful for everything she has done and all that she continues to do.

Thank you, Kathy, for your vision, perseverance, and heart.

📸: [Pat, Kathy, Kristin]

05/14/2026

🚃 Big News from the Wolfeboro Trolley Company!

We are thrilled to announce that Kristin Schepici and Patrick Woods are the proud new owners of the Wolfeboro Trolley Company and one thing is certain: Molly the Trolley isn't going anywhere!

For nearly 40 seasons, Molly has been more than just a ride, she's been a beloved symbol of our community, a smiling face on every street corner, and a cherished part of what makes Wolfeboro so special. Kristin and Patrick are committed to honoring that legacy while bringing fresh energy and excitement to everything she represents.

Whether you're a lifelong local or a first-time visitor, Molly's doors are open and the good times are rolling.

Stay tuned for exciting updates ahead and as always, come hop aboard!

05/08/2026

Molly is s bursting at the seams excited about the big news that’s coming, she can hardly wait to tell you.

05/08/2026

I am so excited and it so hard to not blab it out, but it is a secret for right now

Big happenings at my house - Wolfeboro Trolley Company has an announcement coming in the next couple days that will make you smile!.

Stay tuned right here on our page to find out what it is.

05/05/2026

05/04/2026

🚎 WE’RE HIRING — COME RIDE WITH US! 🚎
Looking for a fun, flexible job where you actually enjoy going to work? This is it.
We’re now hiring Trolley Drivers for the 2026 season — and yes… we’ll help you get there 👇

✨ What makes this awesome:
• Flexible hours that fit your life
• Meet new people every day
• Scenic drives & great vibes
• FREE CDL Class starting May 2026

👤 What we’re looking for:
• 21+ years old
• Friendly, reliable, and enjoy working with people
• Safe driving record
• CDL (Class C or higher) is a plus

👉 No CDL? No problem.

We will train the right person and help you get licensed.

📞 Call Kathy: 603-569-1080
📧 Email: [email protected]

💥 Tag someone who would LOVE this job

💥 Share this post to help someone land a great opportunity

Your next adventure could start right here. 🚎

01/01/2026

Press release - for immediate release.

Molly the Trolley Business For Sale

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 that 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) 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; one more reason for people to choose Wolfeboro as a place to visit, for a day or the whole summer.
“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..’ ”
Anyone interested in more information about the sale may contact Kathy directly at 603-569-1080 or [email protected].

12/31/2025

Here is your chance!! Don't let this opportunity pass you by, call Kathy today!