All Aboard Molly the Trolley: Discovering Wolfeboro, New Hampshire
Article by Nancy Dunmire, Staff Journalist – IPA Magazine Travel
We wanted to be sure to see the most beautiful, historic, lively little towns around us, and it’s no surprise that friends recommended we not miss Wolfeboro, New Hampshire.
We all know that feeling of driving into a town for the first time—not knowing where to park, where to eat, where to stay, or what’s worth seeing. That uncertainty disappeared the moment we connected with Kathy Fairman, owner of the Wolfeboro Trolley Company and the town’s Visitor Center.
From the moment we spoke, Kathy exuded warmth and hospitality. She has owned the trolley since 1987, and with over 40 years of knowledge, she knows every corner, every story, and every hidden gem of Wolfeboro. Her mission is simple: to make sure every guest falls in love with her hometown.
An Evening on Molly the Trolley
In mid-afternoon we were chatting with Kathy, and by 4:30 p.m. we were dressed up and ready to hop aboard Molly the Trolley for an evening of dinner and theater.
Molly herself is a gem—an open-air trolley with traditional oak seats, polished brass rails, and etched windows. We had a great and friendly driver. As we glided through winding backroads, thick forests, and bursts of golden sunset, it felt like stepping into a storybook.
Halfway to our destination, we stopped for dinner at Birch and Vine in Melvin Village. A three-course meal, a big round table, and lively conversation with new friends—it was the kind of experience that makes travel so special.
Back on the trolley, our driver carried us safely to Interlakes Summer Theatre in Meredith, where we were treated to a dazzling performance of My Fair Lady. The quality was Broadway-caliber—exceptional singers, dancers, costumes, and a live orchestra. My husband is still humming “With a Little Bit of Luck,” and every number brought back the nostalgia of classic Hollywood.
By the time we returned to Wolfeboro at 11 p.m., we felt as though we had lived a whole vacation in just one night.
A Daytime Discovery Tour
But the fun didn’t stop there. The next day, Kathy made sure we joined the 1:00 p.m. shuttle tour of Wolfeboro. With Dave’s engaging narration, the town’s history came alive:
-Historic cottages and mansions along Lake Winnipesaukee, some dating back to the 1700s.
-A working dairy farm from 1810 that now serves as a bed-and-breakfast.
-The story of ice harvesting in the winter and the Thursday farmers’ market in summer.
-A 12-mile former railway path, now a beautiful trail for walking and cycling.
-The fascinating legacies of the Brewster family and Thomas Plant, the visionary who built Castle in the Clouds.
We even learned about the mail boat that still delivers letters and packages to the 270 islands scattered across the lake—a tradition that continues to this day and offers tours for curious visitors.
And of course, Dave pointed us toward Wolfeboro’s best dining. He may have even nudged us toward my new favorite restaurant: ‘Morrissey’s’, where the menu is nothing short of indulgent. And Josh’s two restaurants, which we also loved, MARKER 21 and GARWOODS.
Why Start with the Trolley
Every town has layers, and Wolfeboro has more than most—history, scenery, culture, and a lively spirit. A trolley ride gives you the lay of the land so you can decide what to explore more deeply on your own.
But above all, the best part of the Wolfeboro Trolley Company is ‘Kathy’ herself. Her love for Wolfeboro is infectious. She doesn’t just own and drive a trolley—she shares a lifetime of stories, connections, and care that makes visitors feel like part of the community.
For us, Wolfeboro quickly became not just another stop on the map, but one of our absolute favorites. And it all started with Molly the Trolley. Visit the website Wolfeborotrolley and hop on for a great tour!