In this quintessential New England town, celebrity sightings have included Jimmy Fallon, Drew Barrymore, Dwyane Wade, and more.

By Paula Froelich
August 09, 2020
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Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket list adventure.

On a balmy summer evening in June, NBA legend Dwyane Wade, his wife, actress Gabrielle Union, and their son, Zaire, sipped drinks in the front yard of the Pickering House Inn, a boutique hotel in Wolfeboro, New Hampshire, while a camera crew filmed their every move.

Mary DeVries

“Their son is going to [nearby] Brewster Academy in the fall,” said Pickering House owner Patty Cooke. “They’re staying here for the weekend to check everything out.”

Patty’s husband, Peter, was less low-key.

“The basketball games [at Brewster] are going to be really good this year,” he said.

A small group of locals catching up on the porch of the Federal-style house-turned-hotel were nonplussed by the scene – perhaps because they’re used to seeing famous faces in this small town.

Wolfeboro, founded in 1759 and dubbed the “oldest summer resort in America,” is a quintessential New England town set on the shore of Lake Winnipesaukee. It also happens to be a secret celebrity haven.

On any given day in the town of just over 6,000, residents are just as likely to run into Jimmy Fallon, his wife, Nancy Juvonen, and her best friend, Drew Barrymore, at lakefront restaurant Garwoods as they are to stumble upon Mitt Romney having an ice cream with his friend, Marriott Hotel scion Bill Marriott, at the charming creamery Bailey’s Bubble.

But it’s not just celebrities who love this laid-back vacation getaway. Every summer, the town swells from 6,000 residents to 30,000, and Main Street and the waterfront come alive. Tourists and locals park their boats, jet skis, and kayaks at the main dock to partake in waterfront revelry at the bars and restaurants and soak in the sunset and majestic Belknap Mountains reflected in the lake below.

Across from the Pickering House Inn, originally built in 1813 and lovingly restored two years ago, is Cate Park, where, during non-COVID times, bands play free summer concerts and families enjoy picnics.

This year, concerts are on hold and everyone is wearing masks. Carroll County, home to Wolfeboro, has had 77 confirmed cases and one death, and no one is taking any chances. Masks are mandatory and hand sanitizer is placed throughout the buildings that are home to the town’s stores and restaurants.

But even with the modern precautions, the town still retains its authenticity and Norman Rockwell appeal.

Cindy Eagan, a New York City-based screenwriter whose family has been summering near Wolfeboro for half a century, said, “Every time I drive into Wolfeboro for the summer, I see everyone having ice cream, shopping on Main street, and the water from the lake sparkling and the mountains… I just instantly feel like I’ve come home. You feel like you’ve stepped back in time to a simpler place where nothing has changed.”

And it’s not all shopping and eating — Wolfeboro is the epicenter for outdoor enthusiasts in the area, too. Not only is there fishing, kayaking, and waterskiing to be done on the lake, but just off Main Street, near the former Wolfeboro train station, is the bucolic 11-mile Cotton Valley Rail Trail, which is now home to joggers, bicyclists, and hikers coming down from the mountain trails. And further down the road lies Brewster Beach for anyone wanting to take a dip in the water.

“One of my fondest memories is from when I was in college,” recalled Eagan. “I worked as a waitress at Garwoods, which used to be called Aw Shucks, and when I was done locking up and was walking back to my car, I would look around and feel like I was in the most quaint, magical movie set. And I couldn’t believe I got to live there.”

After all these years, “the names of some of the restaurants have changed, but it’s all still the same,” said Eagan.

The oldest summer resort in America is still one of its best.