Wolfeboro, New Hampshire | Could You Live Here?

It may be the most magical name for a lake—and the bane of spelling bees—but if you’re lucky enough to live near Lake Winnipesaukee, then you’re lucky enough. This “beautiful water in a high place” is instantly recognizable on a New Hampshire map: the largest lake in the state and the third largest in New England. That’s 71 square miles of vacation fun (more than twice the land area of Manhattan), dotted with 260 islands. The circumference is scalloped with villages, cottages, and some very fancy retreats, and the water itself is crisscrossed by every flotation device, from paddleboards to the venerable M/S Mount Washington, a majestic 230-foot-long excursion ship. To call it a “popular” summer resort destination is a droll understatement.

Zoom in closer, though, and you’ll find the place where it all started: Wolfeboro, New Hampshire. The nostalgia-tinged sign that greets you on the outskirts of this pretty town welcomes you to “The Oldest Summer Resort in America.” Incorporated in 1770, it stakes its claim based on an early mansion built by Governor John Wentworth on what eventually became Lake Wentworth, just east of Winnipesaukee.

Immediately we conjure images of relaxation infused by water and light; beamy porches and sailboats threading waves; bright cocktails by the harbor. A block from the lake, Main Street does an identity tango between beach town and arts colony, with enough ice-cream outlets to boggle a toddler and a fine scattering of boutiques and art galleries. Plenty of beauty and charm to enchant celebrity tourists Drew Barrymore and Jimmy Fallon, and even, once upon a time, Prince Rainier and Princess Grace. Not to mention summer resident Mitt Romney. So what’s it really like to live in America’s oldest summer resort?

The Setting

“We’re like vacationers in our own town,” says Janet Kenty, sitting with her husband, Jay, at the Downtown Grille Café, overlooking Wolfeboro Bay. Retired newcomers who moved here two years ago, they’re admiring the shimmering waterfront that runs parallel to Main Street, with pleasure boats tethered to the docks, and the mailboat, the Sophie C., tied up in proximity to ducks, kayaks, Jet Skis, and a floating gas station. In the distance, the pale-blue Belknap Mountains hover like a mirage. An adjacent gazebo hosts free summer concerts, and the benches in Cate Park insist that you linger. “There are no stop signs, just one blinking light somewhere, but I don’t know where,” Jay nods.

On the other side of Main Street, the bucolic 11-mile Cotton Valley Rail Trail disappears behind the Wolfeboro train station (today’s Chamber of Commerce), hugging Back Bay and funneling dogs, cyclists, runners, and baby carriages. For a quick dip, there’s Brewster Beach, just past Brewster Academy’s lovely in-town campus; this prep school has been a fixture since 1820.

What about those summer crowds? “We go from a population of 6,000 to 30,000 during the months of July and August,” shrugs Steve Flagg, whose family has owned the Nordic Skier Sports shop since 1972, dispensing skis, rental bikes, and trail wisdom. That’s bound to cause congestion. “We find shortcuts, and parking is at a premium,” Janet Kenty agrees. “But we like driving through town for the same reason tourists do. People are happy, and not in a hurry.”

Social Scene

At the Lakes Region Newcomers Club, Janet notes, you don’t have to be a newbie to enjoy kayaking, knitting, skiing, or photography groups. Culture buffs have options that include volunteering at the Wright Museum—a moving tribute to World War II veterans—or pitching in at the New Hampshire Boat Museum’s vintage-vessel regatta. “There’s a strong sense of community,” Steve Flagg says. “People donate time and money, and even raised $300,000 to enhance the cross-country trails here. All of the trail clearing was done by volunteers.” Consequently, the countryside is crisscrossed with state-of-the-art ski trails that double as bike paths (and Steve’s got the maps to lead you there).

Eating Out

Before you pick a menu, order a sweeping view from one of the bustling cafés and restaurants on the waterfront. Delicate fish tacos at Garwoods might have jumped from lake to plate—the deck is a mere foot above water. And service at the uber-casual Dockside Grille couldn’t be friendlier or more deliciously fried. Inland, it’s a cinch to find gourmet coffee (Seven Suns), ice cream (Bailey’s Bubble, for starters), or freshly baked tarts cozying up to beachy gifts (Gatherings by Stella-loona). Side streets offer goodies like Mise en Place, with French-infused American fare that tempted former French president Nicolas Sarkozy, or Full Belli Deli, with super-big subs that filled up Jimmy Fallon.

Shopping

“I couldn’t do this if it weren’t for the summer crowds,” says Wolfeboro native Jennifer Kalled, gesturing around her elegant Kalled Gallery. Walls glow with incandescent paintings, and blown-glass vases rise up from pedestals like flames. Roughly 200 artisans are represented, including Jennifer herself, whose bold jewelry—such as lace-agate earrings—snatches shards of color from otherworldly stones. Down the street, independent Country Bookseller invites a browse, and Black’s Paper & Gifts does its best to convey what “a store that has everything” should look like.

Real Estate

There was spirited debate at the Kalled Gallery about the state of real estate, but a quick glance at for-sale properties at the time of our visit revealed some intriguing possibilities: an antique Cape on 53 acres for $375,000; a two-bedroom waterfront home on Lake Wentworth for $449,900; a vintage villager with perennial gardens for $239,000; and a furnished cottage on Cow Island for $239,000.

Resident Perks

If you don’t own a boat, you could pretend you have three: buy an unlimited daytime season pass on the M/S Mount Washington, the M/V Doris E., and the Sophie C. mailboat. In the wintertime, residents can ski at community-owned Abenaki Ski Area. “We’ve got the oldest, smallest ski area in the country,” Steve Flagg says proudly, and it’s just three miles from downtown. (Gunstock Mountain Resort is only a half-hour away, too.)

Getting Your Bearings

A quick walk from town, the historic Wolfeboro Inn (1812) has its own beach and a lively bar/restaurant, Wolfe’s Tavern.

This feature originally appeared in the July/August 2016 issue of Yankee.