Reliving Childhood Memories with a Ride on Molly the Trolley

By Kathi Caldwell-Hopper

My kids knew more about Lakes Region tourism and interesting places to go and things to do by the time they were five or six than most children know in their entire childhood. That was simply because my kids, Dan and Megan, often accompanied me on story interviews and excursions when they were young. We went to Sculptured Rocks, to Polly’s Pancake Parlor, to try out the latest jet skis, to ride wagons to remote blueberry fields and on and on the list of fun places went as I did stories for The Laker.

But nothing was as much a beloved part of my kids’ growing-up years than Molly the Trolley. The co-owners of the Wolfeboro Trolley Company in Wolfeboro were also the co-owners/founders of The Laker (newspaper), Dick and Kathy Eaton. When we dropped by the newspaper office to turn in my weekly stories, Dan and Megan would especially like to say hello to Dick in the hopes he might give them complimentary trolley ride tokens. I am happy to say he always obliged, which helped to create wonderful memories for my now-grown-up kids. 

We rode the charming trolley on many a hot summer’s day, and we even rode it when it was rainy or overcast. In all sorts of summer weather, a trip to Wolfeboro held the promise of a ride on the trolley. 

Molly the Trolley and Kathy.jpg

Molly the Trolley with driver/co-owner Kathy Eaton

(Courtesy photo)

My kids are now in their late 20s, and live out of state. Their schedules are such that they have not been to Wolfeboro in ages, and that is probably why my daughter, Megan, was hankering for a day in downtown Wolfeboro when she was home on vacation. 

It was a very hot July day when we casually browsed downtown Wolfeboro. By mid-afternoon, we decided to get an ice cream at Bailey’s Bubble on the corner of Main Street and Railroad Avenue. Our plans got a bit off schedule when Megan saw Molly the Trolley drive by and heard the call of the trolley’s bell. As she would have as a child, she started walking towards the bright red trolley, which was parked by the former Railroad Station, one of the trolley stops where passengers can get on board.

We heard a cheerful voice say, “Is that Megan? Are you here to take a trolley ride?” There was trolley driver for the tour, Kathy Eaton. 

We stopped to say hello and to reminisce a bit about my kids loving all those Molly the Trolley rides when they were kids. After chatting and getting caught up on how Megan is doing, Kathy asked, “So, do you want to take a trolley ride?” That was all the invitation Megan needed to nod yes, and we were soon seated on a shiny wooden bench with a great window view.

There were some visitors who also were seated and taking the trolley tour around Wolfeboro. They were from Florida, and I wondered how different the Lakes Region would be to them. Certainly, the hot and humid weather was Florida-like, but New England’s long history as the place where our nation was born would be quite different.

After making sure we were seated and settled, Kathy took the driver’s seat and we were off! There is no doubt that downtown Wolfeboro on a summer’s day is bustling but Kathy maneuvered the trolley skillfully and I noticed many people smiling and pointing to the Victorian-style trolley. It is indeed difficult to spot Molly and not smile; there is just something so fun about the trolley!

During the tour, Kathy used the onboard speaker system to tell us the narrated story of all we saw along the way, starting with information about the 1872 Railroad Station, which is now used as a Chamber of Commerce information center, and also houses Wolfeboro Jet Ski Rentals.

As we moved through downtown Wolfeboro, Kathy pointed out businesses and mentioned that famous people often visit the town, such as summer residents Mitt Romney and his wife Ann, and television personality/comedian Jimmy Fallon and his wife.

Kathy pointed out downtown businesses and restaurants and mentioned several art galleries, including the Art Place, and as we turned onto the Back Bay area, she told us about the Abenaki Water Ski Club. Club members practice during the summer on the waters of the bay area. Also mentioned were the Back Bay Skippers, who meet at the Back Bay area to race their radio controlled boats.

We next headed up North Main Street, where Kathy pointed out the Wolfeboro Inn, which was built in 1812 as a private home for Nathaniel Rogers. In the 1930s, it became the Wolfeboro Inn. Kathy also mentioned the Inn on Main Street and the barn, where functions are held, and the Libby Museum, just up the road a way on North Main Street.

I personally found the side trip we took on Sewall Road to be just my kind of thing. Kathy told of the origins of many of the old homes on the road as being in the Roaring 20s, when wealthy people wanted to bring their vacations and parties to the Lakes Region. We drove by many large waterfront homes, all immaculately tended. As we neared the end of Sewall Road, which put us back on North Main Street, Kathy pointed out Goodhue and Hawkins Marina. It was here that Castle in the Clouds owner Thomas Plant came to get a Laker boat built. His specifications were that he wanted his boat to be one foot longer than the standard Laker. The boat was 33 feet long. It is now called the Keen Cutter.

The trolley next stopped at the town docks area, where Kathy parked for a few minutes so that new passengers could get onboard if they wished. While stopped, Kathy pointed out the commercial dock where four boats offer lake cruises, including the Mt Washington, Winnipesaukee Belle, Millie B and US Mailboat.

Kathy has lived in Wolfeboro for a number of years and really knows the history of the town. She told us about the railroad and its last station on the line right near the waterfront.

Also, she pointed to Cate Park in the dock area, where free Saturday night concerts take place each summer, as well as Wednesday night Cate Park band concerts. 

Next, we headed to South Main Street, where we passed Brewster Academy, another place with a long history. Kathy told us the circa 1820 academy was, at one time, Wolfeboro’s high school. She also told us of the Pavilion Hotel, built in this area long ago by Daniel Pickering.

Not far away, our next drive by was through the Clark House museum complex with its historical buildings open to the public. Among the structures is a Fire House Museum, where a volunteer on duty came out to tell us a bit more about the buildings and what we would see should we visit. He also told us that the recently completed barn on the property is now open and full of fun and interesting artifacts.

Up the road a bit, we turned around in the Kingswood High School parking lot. Kathy at this point told us about the Kings Woods history; in the 1700s, England has just about exhausted its supply of tall trees which were perfect for making ship masts. Thus, upon settlement of the Wolfeboro area, the King of England decided the area would be known as the King’s Woods and all the tall trees (over 24 inches in diameter) therein would be the property of the King to be used as ships masts.

After turning around, we headed back towards the downtown Wolfeboro area and made a right-hand turn onto Center Street. Kathy pointed out the Wright Museum of WWII and further down the street, the NH Boat Museum. Also mentioned were the 1810 House antique shop and winery, the Cotton Valley Trail, and Albee Beach, which was just one part of Allen Albee’s grand summer vacation complex called the Allen A Resort.

All too soon we were back and parked once again as the area by the Railroad Station. We chatted with Kathy for a few minutes, learning that the trolley leaves on the hour from the Wolfeboro Town Docks and on the half-hour from the Railroad Station. Narrated tours are 45-minutes long. The trolley runs daily in July and August, from 10 am to 4 pm and on weekends in spring and fall from 11 am to 2 pm. The Wolfeboro Trolley Company also offers private charters; call 603-569-1080 or visit for more information. (It is a good idea to call or check Facebook to confirm Molly’s tour schedule as private charters interrupt her regular schedule occasionally, especially on Saturdays.)

After our trolley tour, we were more than ready for ice cream from Bailey’s Bubble, a short walk back down Railroad Avenue. Megan got to relive a sweet part of her childhood with a trolley tour and we ended the afternoon the best way possible, with ice cream…and some great memories.

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