Wolfeboro, New Hampshire | Could You Live Here?
The place where it all started: Wolfeboro, New Hampshire (population 6,269). This pretty lakeside town welcomes you to The Oldest Summer Resort in America.
By Annie Graves|May 18 2017|
Coffee By Design | Portland, Maine
Photo Credit : Katherine Keenan
Photo Credit : Douglas Merriam
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 (population 6,269). 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 Grill 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.
Photo Credit : Kindra Clineff
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.”
Photo Credit : Kindra Clineff
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—or to join the club’s First Friday Breakfasts at the Wolfeboro Inn. 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).
Photo Credit : Kindra Clineff
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 publication 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 if you pick up an unlimited daytime season pass for the M/S Mount Washington, the M/V Doris E., and the Sophie C. mailboat. In the wintertime, residents can ski for $8 a day 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.)
Photo Credit : Kindra Clineff
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. 90 North Main St. 603-569-3016; wolfeboroinn.com
SEE MORE: Wolfeboro, New Hampshire | Photographs
This is a wonderful article. I was blessed to not only be born and raised in Wolfeboro, but blessed to have raised my own children here. I’m the nurse at a boys’ camp on the lake and my grandchildren are now growing up in this beautiful town. One point of order, though: the US Mailboat in Wolfeboro is not the Sophie C. The Sophie C services the other half of the lake and does not dock in Wolfeboro. The Blue Ghost captained by Sandy McKenzie services Wolfeboro and this end of the lake ????
My two uncles, my mothers brothers, the late Eddie and Bill McMorrow, spent at least 2 weeks every summer in the 40s ,50s and 60s at the Lakeview Inn in Wolfeboro. They brought me there many times and I loved it. The Hill Family owned Lakeview and there were lots of regulars who came every season. I remember riding on the Mt Washington, eating lunch at Dockside swimming in Lake Winnepasaukee and how you could see to the bottom it was so clear. I’m 75 now and hope to go back in the Fall.
You mentioned you could see to the bottom. Does this mean that all of the Lake was not very deep and how was the fishing?
The deepest part of the lake is 212 feet with an average depth of 43 feet. The water is very clean and clear which is why you can see to the bottom in many places.
There seems to be a lack of Retirement Communities for over 57…Did I miss something?
There are two retirement communities in Wolfeboro, Sugar Hill and Taylor.
I reside in the picturesque Hudson Valley of NY state. Recreation, culture and history. Wolfeboro, captured the essence of (also) a beautiful place to be.
We have summered in and around Wolfboro all my life and now my “kids” do the same. My great grandfather owned property in Glendale years ago, so it’s. Ertainly a family tradition. I would live there in a heartbeat! It’s the most wonderful place in the world to me…
Always loved Wolfboro, but could never live there, nice weather for only about eight weeks of the year. Nice weather to me is above 75 degrees! Hope to visit there in July.
My mother was born in Wolfeboro and my Grandparents owned two hotels in Wolfeboro, decades ago. We went there every summer, as children and then Camp Bernadette, as my daughter did years later. It’s a warm and welcoming town that provides you with wonderful memories!!!
We vacationed in Wolfeboro for many many years – but our house was on Lake Wentworth. Summer means Wolfeboro to me!!!
All it took for us were a couple of day trips last Summer to decide that Wolfeboro was where we wanted to luve. Sold our house in the southern part of the state and we are currently building a home in Wolfeboro.
If living somewhere could be equated to “comfort food” then Wolfeboro/Tuftonboro would be me my “mac & cheese” of geography!
I am repeatedly hearing Wolfeboro is not friendly to dogs? I
A lot of the shops downtown are very focused on tourist dollars… People walking dogs not purchasing is what’s bothering them
Regarding the comment about hearing that Wolfeboro is not friendly to dogs…I have not observed that myself, as a matter of fact there’s lots of people that have dogs and the Woof- boro pet store is one of the first things you see when you drive into town. Store owners put water bowls out for peoples’ dogs. I have a couple dogs myself. I just moved here less than a year ago and I have never felt like it was not dog friendly. There so many people that go and walk their dogs on the Cotton Valley Trail as well. It’s a very nice place to have dogs and we have a dog park at the Nick.
Wolfeboro is very dog friendly. All of the shop owners in the town even put out water along the sidewalks for the dogs in the summer. There is also a dog park at the Nick. And lots of dog friendly activities.
Recently built a log home about a mile from down town and its the best thing we’ve ever done!! Its gorgeous year round even in winter with the snow capped mountains in the distance!!
The lake area is beautiful… but there is a REAL decide with The visiting rich to the lake (and the locals ) there is A lot of Poverty and little In the way of Economic opportunities…. Education is not a priority . Living there full time I would not recommend it.
I lived in Wolfeboro from 1957-1967 – 3rd grade thru High School (Kingswood). My parents owned The Wool Corner until 1973. I cannot think of a better place to have grown up. How I miss the summers there!
As a young boy, in the late 50’s I worked at the “Allen A Summer Resort” on the shores of Lake Wentworth, just up the road from Wolfeboro. It was my first summer job away from home. It was agreat learning experience and I remember Wolfboro well. It was so beautiful with friendly people and that lake!
I’ve since traveled to many countries and communities but still Wolfboro registers as one of my top destinations.
Many meaningful memories as a young kid trying to grow up.
Thank you, Wolfeboro
My family vacationed there in the late 60’s-70’s. I have such wonderful memories at the Allen A.
Spent two great summers at Camp Bernadette as a counselor…great memories,even clout shooting at the golf course with my campers. Is the camp still there?