How to Dock-Hop on Lake Winnipesaukee

On a pontoon on the blue waters of Lake Winnipesaukee, it dawns on me that maybe I am a lake person.

I never saw myself as much of one (all of the lakes in Oklahoma, where I grew up, are muddy and artificial), but out here in central New Hampshire, I’m going dock to dock, looking for loons in secret coves, stopping in towns for fresh ice cream, and taking quick hikes on some of the 250-plus islands.

It feels like when Obi-Wan tells Luke in Star Wars, “You’ve taken your first step into a larger world.” It’s a fun step.

Originally I had planned to drive around this 72-square-mile glacial lake that’s been a holiday destination for New Englanders for over a century. But once I got here, it became clear the draw is getting on the lake itself. Though I’ve never driven a motorboat and have no boating license, I learn you can rent motorboats or pontoons 25 horsepower or less without one.

That’s my plan.

I’m leaving the Wolfeboro docks in the southeastern edge of the lake where I’m staying, armed with a breakfast sandwich and some laminated maps of the lake. Tom Wachsmuth from the Wolfeboro Corinthian Yacht Club keeps my pontoon lessons simple. He advises me to head toward the home of Jimmy Fallon’s wife’s family across the way, then stay on the northeast side of the black buoys and the southwest side of the red ones. (Or was it the opposite?)

“Just don’t hit the blade on a pier,” he deadpans.

So I head off, gathering confidence by the time I leave the bay and reach the open waters.

Set back in a peaceful cove a 45-minute ride away, I spot my first stop. The Libby Museum, opened in 1912, has its own dock. I go toward it tentatively, putting the boat into reverse to slow down, and surprise myself by parking on my first try.

Named for dentist Henry Forrest Libby, the museum is opening for the season today. Inside the columned exterior facing the water, I find a time-warp collection of animals and objects.

Display cases are signed in the dentist and his wife’s careful print. There’s a puffball mushroom, pottery shards, caribou and moose skeletons, and a display of a stuffed beaver. Later additions include Native American dugout canoes that were found buried in the lake by four boys in 1955. One display case features the disarticulated skeleton of a house mouse set out on green felt. I’m charmed.

On my way out, a museum employee stops me. “Did you see the mummy hands? Kids love those.”

I peek at them and get back on the water. I head across the lake toward Rattlesnake Island, a hilly two-mile woodsy island that’s typically off-limits to the public. (I was a visitor of Wachsmuth’s.) But the open water’s stronger than back at the cove. I make a few clumsy attempts to dock and fail. Naturally, a local happens by to witness these blunders and eventually offers some advice and helps me tie up the boat.

I follow the rocky trail up the first hill, about a third of a mile off. Thin rays of sun cut through the thick forest leaves. Above are granite ledges, where I sit, eat a fig bar, and look over the 180-degree view of the southern part of the lake.

Lake Winnipesaukee, named for the Native American tribe that once lived here (one possible meaning is “beautiful water in a high place”), has inspired much literature and art. To me, though, the best has to be Adam Sandler’s line in “Thanksgiving Song” from a Saturday Night Live episode in 1992:

Gobble gobble dee
Gobble gobble dockie
I used to go to camp
At Lake Winnipesaukee

Sandler grew up in New Hampshire, and some of his movies take place on the lake. (Mr. Deeds is set in a town like Wolfeboro, but was shot in Connecticut.) Lately, a rumor is circulating here that he’s bought a $49 million property on the lake. (Wachsmuth assures me it’s not true. “And I have connections in real estate,” he says.)

As I ride south, up a narrow bay to the town of Alton for lunch, I dream of the lakeside homes I’d like to own one day. Most are backed with green hillocks that look something like ‘70s shag carpet.

In Alton, I tie up in a mostly empty dock and have a chicken Caesar salad on the deck of Shibley’s at the Pier. Across the road, they run a drive-in ice-cream stand, part of New Hampshire’s Ice Cream Trail. The portions I find at many of the stops emphasize size. I get two giant scoops (coffee and pistachio) and head back to the boat to slowly ride back—circling islands as I go—to Wolfeboro.

After I return the pontoon undented, I ask Wachsmuth about other ways of seeing the lake. I’m surprised to learn diving is big here. He leads visits of the lake’s underworld, which includes sites where Native Americans hid dugout canoes.

Next time, maybe, I’ll venture farther into the Winnipesaukee—under the surface.

How To Take This Trip

The road around the lake rarely goes along the shore, so it’s wise to consider where you’ll base yourself. Weirs Beach, on the west side, is the busiest hub. I picked Wolfeboro instead, which bills itself as the country’s oldest summer resort. There are several museums and restaurants, as well as a brewery and rails-to-trails bike paths. I stayed at the Wolfeboro Inn, a nice hotel next to the pontoon pier.

You can rent a pontoon from Wachsmuth at Wolfeboro Corinthian Yacht Club, or an open-top 13-foot Boston Whaler (boating license required) at Hole in the Wall. Prices start at $250 for the day, including life jackets and gasoline.

Arrange diving trips of the lake’s clear water at Dive Winnipesaukee in Wolfeboro.

A block from the Wolfeboro docks, Seven Suns Coffee is a good place to get a coffee and breakfast sandwich to start your day.

If you don’t want drive a boat yourself, boat tours include the historic Mount Washington, which leaves most days from Weirs Beach.