Breakfast with Jenny Dewar: Business owner talks love, loss and what she wore

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BENNINGTON — For Jenny Dewar, all roads have led to Pownal.

And she's traveled many roads.

The community volunteer and short-term vacation rental business owner grew up in New York City to parents from Oxford, England and Albuquerque, New Mexico. She's since lived in places such as Miami, Korea and Sweden, and has never spent more than four years in one location.

That is, until Pownal.

She's been living in town for 13 years thanks to a move that was initially "random," she said.

"We had friends who moved here, we started looking at real estate just for s---- and giggles, and then we said, 'Oh hey, let's put our house on the market and see what happens,'" she said. Mere weeks later, they had sold their house.

"And then we're like ... 'Now we really need a place to live,'" she said. "So we decided to up and move here with no plan."

Dewar shared these memories and others with the Banner at the Blue Benn Diner in Bennington one recent sunny Wednesday morning. She had a Greek omelette with sourdough toast and "really, really well done, crispy crunchy" potatoes with tea.

In her years in Pownal, Dewar has spent time on multiple efforts, including her business, called Karin's Place, renting her late parents' former home for events such as corporate retreats, health and wellness retreats, family reunions and wedding accommodations.

"I'm happier now than I've been with work," Dewar said. "I love working for myself. I was always meant to be an entrepreneur."

It wasn't always that way. The deaths of Dewar's parents, and questions about would become of their country home, led to a confusing time.

At the time of Dewar's move to Pownal with her husband, her mother was suffering from early onset Alzheimer's disease. She moved to the family's country house in Pownal full-time, and lived with the condition for 20 years before her death in 2013.

Dewar's mother first started showing symptoms when she was about 48, and was diagnosed at the age of 53.

"And that's the age I am now," Dewar said. "So I will be 54 in December, and that's when I feel like I will finally fully grieve."

Two years later, in 2015, Dewar's father died of colon cancer just after his 70th birthday.

Dewar's major task after her father's death was to get the country house up and running for rentals. She'd promised to save the place and keep it full of people, and she couldn't do that unless it generated income. "Everything was just turned upside down," she said of that confusing and unsettled time.

But the work of getting the business up and running had its own way of pointing her in the right direction.

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"I remember there was a day I was driving, and I was like, 'What's this feeling? I'm having a really weird feeling,'" she said. "And I was like, 'Oh, it's happy. That's what happy feels like. And "I suddenly like saw the mountains, and was like, 'Wow, it's beautiful here.' And then it was like we were here by choice. We weren't here because we were stuck here."

Pownal has grown to feel like home for Dewar and her husband, John.

"Where else would we go?" she said. "This is home. This is where we live. Our roots have grown deep."

Besides owning Karin's Place, Dewar is also a property manager for Quarry Hill Farm in Pownal.

"Being here by choice — that's when we finally allowed our roots to grow," she said of Pownal.

Dewar started doing what she loves, which is getting involved in her community. She joined the Economic Development Committee, now the Pownal Business Network.

"That's when I got more involved, when I got onto that committee," she said. She created a website listing town businesses,

After that, Dewar ran for the town's Select Board. She resigned in November 2018 with four months left in her one-year term, citing a conflict with a fellow board member.

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She said one of her goals was to get more people aware of local government.

She recalled the town's 2017 vote on a proposed Act 46 merger with Bennington, Pownal, Shaftsbury, Woodford and the Mount Anthony Union school districts. About 400 people voted out of 2,600 eligible voters in Pownal. The merger failed by four votes in Pownal, and the state Board of Education later mandated a similar merger.

"This was going to affect our taxes, and our school board, and only 400 people voted," Dewar said. "One of my goals was to get more people aware of local governance, and pay attention to it."

She thinks she succeeded.

"I've always been active and involved, and volunteering," she said. "I care passionately about my causes — right to legal abortion is one of my main causes, equality among all people, whether you be black, brown, gay, straight, woman."

She said she "came out of the womb as a feminist."

"My mother raised me to be the woman that she was intimidated by in college," she said.

Dewar's mother grew up extremely poor in Albuquerque, New Mexico, and was a first-generation college graduate. Dewar's father, a computer scientist, had his doctorate and was a professor by the age of 23.

"He was a bona fide genius," she said. "That's not a compliment. Being a genius is not something I wish on anybody."

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Dewar is also no stranger to the stage.

Before moving to Pownal, she worked extensively in the New York City art world, including eight years as a dancer after leaving college, initially in modern dance.

"When I realized I couldn't make a living that way, I became a showgirl," she said. "So I went to Miami, put on feathers and a g-string, and spent six months there."

From there, she came back to New York and did musical theater as a dancer who would also act and sing.

She met her husband, a trombone player, during a production of "Jesus Christ Superstar" in Germany, she said. She was performing in the ensemble. He was playing trombone.

"He followed me home," she said. "He didn't have anywhere to stay, so he stayed with me, and he still hasn't left."

The couple has been married for 22 years. Dewar fondly recalls how her husband figured out which person on stage was her.

"So we had these G-strings and fishnets and boots up to the thigh He went around on opening night looking for my a--. He was literally looking for my butt. And he was like, 'Are you the one all the way on the left?'"

When he found her, Dewar said, she was standing with her father, who happened to be in Germany at the time.

"He looked and was like, 'Yep, that's you,'" she said. "And then he ran away."

After dance, she spent 10 years in stage management on Broadway, working on shows such as Fiddler on the Roof, Cats, Chicago, Neil Simon's Dinner Party, Macbeth, Our Town, Rent and Ragtime. She also stage-managed at the Williamstown Theatre Festival in Williamstown, Massachusetts, early in her time in Pownal, which led to a longtime position as the concert and event manager in the college's music department.

Dewar's husband teaches trombone at Williams College in addition to playing professionally.

Besides their jobs, Dewar and her husband have much to occupy them in Pownal.

"And we have all these animals," she said, listing them off: eight cats, three goats and two chickens.

"We got rid of the rooster," she said. The rooster, Chicken Ala King, now lives at Harwood Homestead.

"He is behaving himself totally, a hundred percent," Dewar said. "And I'm like, nobody is ever going to believe that he was attacking me."

Patricia LeBoeuf can be reached at, at @BAN_pleboeuf on Twitter and 802-447-7567, ext. 118.


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