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Cigar bar is Everett's latest business venture in Lakeport

Sir Winston's to open as private club later this year

By JANICE BEETLE, for The Laconia Daily Sun Sep 8, 2025 

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LAKEPORT — A French bulldog named Sir Winston is taking up residence in Lakeport Square.

He is brown, rather pudgy and sporting a yellow bowtie and red ball cap, and a cigar hangs from his mouth. Sir Winston is the eccentric icon for developer Scott Everett’s latest venue: Sir Winston’s Private Cigar Lounge, at 777 Union Ave., next to the Lakeport Opera House.

Named after Everett’s own 1-year-old dog, the club’s mascot is one of the more fanciful touches for the cigar bar, which will otherwise be sophisticated and inviting. The brick façade on the front of the building will set an opulent tone with the Sir Winston's signage, a series of tasteful lanterns and a large picture window with dark wood trim and gold accents.

The front of the building will not have an entrance, though; club members will arrive via a door off the alley to the right, and enter via a smartphone app.

For an annual fee, 100 members can visit daily, and each will have a private, wooden alcohol and humidor locker to store their own spirits and cigars. Sir Winston’s will not be licensed to sell either.

Everett is also creating black leather jackets, with the Sir Winston logo emblazoned on the back, for each of the club’s founding members.

“It’s going to be a cool little club,” he says, noting he has so far sold 50 memberships. “Like Cheers. People will know your name.

“I wanted a cool place to hang out with really good friends."

Why a cigar bar?

A year ago, Everett bought the building that will house Sir Winston’s from Justin Spencer of the band Recycled Percussion and owner of the Chaos & Kindness store formerly located there.

Everett didn’t immediately know what he wanted to do with it. “It’s a unique spot, and I had a bunch of people ask me to take it,” he said, adding he immediately ruled out businesses like a restaurant or café because they require too much parking capacity, which is already at a premium.

He eventually landed on a private cigar bar.

Members may bring up to three guests without additional fees, and each individual guest is welcome up to twice per month.

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Inside with Sir Winston

Currently still under the final phases of construction, Sir Winston’s will have the classic elegance and ambiance which city residents have come to expect from Everett, who designs all his own projects. His creative mind is always firing, and so he says none of the lounge plans are 100% set in stone, including the hours, which at present are 8 a.m. to midnight.

Renderings show cozy touches, such as a library nook in the back, complete with books for members to read and a table with a chess game atop it. Some good competition will also be had at the 22-inch shuffleboard table, and members can watch what they’d like on an 80-inch television.

A rustic, stone fireplace will offer warmth and a touch of home at the front of the building, with the bar — which will be dry and unmanned — across from it.

Even the deep green wall tile and black-and-white flooring in the club’s two bathrooms add to the overall feeling of luxury.

Everett plays with the notion of Sir Winston’s as home to Lakeport’s modern-day Rat Pack, harkening back to the days of Frank Sinatra, Dean Martin and Sammy Davis Jr.

“Life should be fun,” he said, “and people get so serious they forget that.”

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Making Lakeport a ‘premier’ location

Everett grew up in the Lakes Region, as did his parents and grandparents, and he calls himself “a lakes kid.”

As Rusty McLear revitalized Meredith with offerings such as the Inn at Mill Falls, Everett says he is on a journey to make Lakeport a premier destination.

His projects to date include the renovation of the Opera House and the development of 51 Elm St., which offers retail space and 20 condominiums. Sir Winston’s is “a small, third idea that will fit in really nice.”

He owns at least seven other properties in Lakeport, and has previously discussed creating an extension of the WOW Trail along Elm Street, and the development of Opechee Place, another multi-use complex, near Lake Opechee Inn and Spa.

Currently, he is in waiting mode, discerning how receptive the community will be to these ideas. He has sold eight of the 20 condos in 51 Elm, and thinks buyers might be waiting for the cost to decline. “It might go the other way,” he said.

The retail spaces are all full at 51 Elm, and doing “really, really well,” he added.

Those interested in membership at Sir Winston’s Private Cigar Lounge can visit sirwinstonscigarlounge.com to submit a request. Openings are offered by invitation as availability allows.

For more information, call 603-461-8025, or email Alicia Kasselman at [email protected].

Source: https://www.laconiadailysun.com/news/local/cigar-bar-is-everetts-latest-business-venture-in-lakeport/article_7485fd7e-0d8a-49fe-b462-29ab71f0bad7.html

  • Thanks 1
Posted

Sounds fun. It's just over 2 hours away from me. That is in Laconia which has the biggest biker week in the Northeast. He'll make a killing that weekend.

  • Like 1
Posted
7 hours ago, BrightonCorgi said:

Sounds fun. It's just over 2 hours away from me.  

On the face of it, this seems pretty sweet; $125 a month gets you a place to come any day of the week to smoke cigars unencumbered, hang out with seemingly like minded individuals, and not be pressured to buy any of the house items. 

  • Like 1
Posted
12 hours ago, Hoosh said:

On the face of it, this seems pretty sweet; $125 a month gets you a place to come any day of the week to smoke cigars unencumbered, hang out with seemingly like minded individuals, and not be pressured to buy any of the house items. 

If it were a 24/7 available member lounge like Portmann's then it would be a lot more interesting.

  • Like 2

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