A Day in Wolfeboro with Molly the Trolley

PHOTO: Molly the Trolley making her rounds near Brewster Academy with Wolfeboro Bay and Mt. Major in the background.

by Kathy Fairman
Contributor

It was a perfect August day with plenty of blue sky and sunshine when I set out to spend a day with Molly the Trolley in Wolfeboro, located on the northeastern shore of Lake Winnipesaukee.
“No need to pack a lunch,” Molly emailed me when I requested information. “There’re plenty of great places to eat here, several on the water and many with expanded outdoor seating. Just tell me what kind of food you want, and I’ll tell you the options.”
With Molly’s 33 years of experience introducing people to Wolfeboro, I figured I was in good hands.
As I planned to spend the day, Molly advised I park in the Glendon Street Parking Lot where there is no time limit; all the parking in Wolfeboro is free. It was an easy, short along the water on the Bridge Falls Path to the Wolfeboro Railroad Station where I would meet Molly for a tour of the town.

Molly The Trolley at the Wolfeboro Train Station.

Arriving early, I followed the aroma of freshly brewed coffee across the street to Seven Suns Creperie where I discovered why the coffee smelled so good; here it’s freshly roasted, as well as brewed!
On my tour I learned Seven Suns is one of two coffee roasteries in Wolfeboro, the other being Lucas Coffee Company on King Street; you can buy from either on line.

Covid -19 Precautions in Place
Molly arrived right on time. I expected to wear a face covering on the trolley and was prepared, but I was pleased to see free masks and hand sanitizer offered at the door as well.
I have to admit I felt a bit like an undercover agent with my hat, dark glasses, mask and notepad, but of course, I looked like everyone else.
The driver explained that to be safe, the trolley is presently divided into three sections to provide distancing between groups. Red satin ribbons cordon off seats separating the areas.
A family of five boarded first and took the section in back. I was directed to the center section, which could have accommodated eight. However, I as I was on my own I was considered a group of one and had the entire section to myself. I felt very safe and relaxed. An older couple with two grandchildren sat in the front area.
I purchased my All-Day Pass from the driver, but I could have bought it on line in advance and called to reserve a time. The driver provided me with Molly’s Map/Brochure which I found very helpful, especially after the tour.
Pulling away from the Railroad Station (barn red with gold-trim) I learned it was built by the Boston and Maine Railroad in 1872. It houses the Wolfeboro Chamber of Commerce and Information Center (Open Monday Saturday 10-6,) Wolfeboro Jet Ski Rentals, and public rest rooms. There’s also an adorable playground that looks a train behind the station.
I was distracted from my note-taking by the beautiful lake views and picturesque waterfront downtown, most of it built in the 1800s. I felt like I’d stepped back in time, perhaps into a Norman Rockwell painting.
You can walk everywhere and there’s a nice variety of shops, art galleries, restaurants, bakeries and places to get that summer favorite, ice cream.
Some store names are especially fun: Winni Paw Station (pet store,) Country Bookseller (bookstore,) Penny Candy (owner’s name is Penny,) Butternuts (kitchen wares,) Made on Earth (clothing) and Dive Winnipesaukee (everything for water fun.)

New Hampshire Boat Museum.

Leaving downtown we visited Back Bay where from WolfeTrap Grill & Raw Bar we saw courses for the Back Bay Skippers (RC sailboat racing) and the Abenaki Water Ski Club (slalom and jumping since 1981.)
I especially enjoyed Molly’s tour of Sewall Road where I saw some of the beautiful waterfront homes Winnipesaukee is famous for including cottages built a century ago, a new mansion just completed, and others built in the years between. And I learned about some of the famous people who have, or now live in them.
Molly stopped at Goodhue and Hawkins Boat Yard on Sewall Point where we looked back across Wolfeboro Bay viewing the town from the water, easily identifying Brewster Academy, Wolfeboro’s private coeducational high school, the Wolfeboro Town Hall clock tower, and the big yellow Avery Block, both built in 1890.
Stopping at the Wolfeboro Town Docks back downtown we learned that the US Mail Boat (Call 603-569-8080 for reservations) is offering daily cruises Monday-Saturday with some restrictions.
The M/S Mount Washington (running only out of The Weirs this year), Millie B and Winnipesaukee Belle all plan to be back in Wolfeboro with cruises and boat rides in 2021.
The vistas of Wolfeboro Bay and beyond from Brewster Academy took me away from my notepad again as we began the second half of our tour where I learned about Wolfeboro’s colonial history.
The town was named in 1759 for British General James Wolfe, a great hero of the French and Indian War; Kingswood Regional High School and Kingswood Golf Course on South Main Street are located in what was King George III’s woods in the mid-1700s, so prized by His Majesty that one could be hung for poaching a tree! And Molly knows the reason why.
Molly’s tour took me through Wolfeboro Falls where I discovered the other end of The Bridge Falls Path. There it connects with the Cotton Valley Trail which continues beside the railroad tracks for 12 miles over causeways crossing both Lake Wentworth and Crescent Lake to the Town of Wakefield where the spur line began in 1870.
We circled the Winnipesaukee Winery where I saw folks enjoying outdoor wine tasting under a canopy while others shopped for a treasure in the huge two-story 1700s antiques barn, one of three antique shops in town (Back Bay Antique Gallery, Mari’s Treasures, Wolfeboro Antiques and Artisans.)
More beautiful views of those causeways and lakes came my way as Molly explained that Lake Wentworth is named for Governor John Wentworth, the last governor appointed by King George before the American Revolution.
Wentworth built a summer mansion on Lake Wentworth in 1772 and that’s why Wolfeboro is known as the “Oldest Summer Resort in America.”
“So that’s why…” The family in the back was chatting. “I’ve been coming here all my life and I always wondered…”
The older woman in the front piped up “Don’t feel bad; I was born here, and I’ve learned a lot today myself. We came to give the grandkids a ride, a break, you know? But I never expected this. I’m going to bring their parents next time!”

Wolfeboro Town Hall.

I smiled behind my mask and dark glasses as Molly’s driver led us all in a rousing chorus of “The Wheels on the Trolley” delighting the youngest passengers.
Following the tour, I went back to Molly’s Map, appropriately named “Discover Wolfeboro,” and planned the rest of my visit.
The Wright Museum of World War II History, the New Hampshire Boat Museum and the Libby Museum of Natural History all recommended by Molly the Trolley were at the top of my Must-Do list. I wasn’t at all disappointed and next visit I’ll allow more time at all three.
From the “Where to Dine” section I selected lunch and dinner spots and, as I’d already decided I needed to stay for at least another day, I booked a room at one of the inns listed in the “Where to Stay” section.
I could have done that on-line as everything in the brochure is also on Molly’s website, wolfeborotrolley.com, or I could have called 603-569-1080.
Now that I’ve “Discovered Wolfeboro,” you can be sure I’ll be back. Now where did Molly say I could rent a cottage for a week?

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