Love Letters to Portland: Julia + Dan Bailin, Jen DeRose + Sam Kilbreth, and Briana + Andrew Volk

  • Julia and Dan Bailin. Photography by Greta Rybus

  • Jen DeRose and Sam Kilbreth. Photography by Greta Rybus

  • Briana and Andrew Volk. Photography by Greta Rybus

If you have ever driven to Maine, it’s likely you have seen the big, blue welcome sign at the border announcing a state slogan: Maine, The Way Life Should Be. In so many ways, that sentiment rings true for those of us who live here. Our food traditions, steeped in farming and fishing, inform our passion for cooking simply and with the best local ingredients. Our sense of play is invigorated by beautiful and vast natural landscapes. And our creative communities bring life, dynamism, and energy to the cultural fabric of the state. There is an innate joie de vivre that is uniquely Maine. More and more, young professionals are choosing to abandon their former lives and flocking to Portland for a better work-life balance. Three couples—Julia and Dan Bailin, Jen DeRose and Sam Kilbreth, and Briana and Andrew Volk—share their stories of why they chose to call Portland home.

It happened every single time Julia and Dan Bailin would cross the state line into New Hampshire. A feeling of anxiety would sink in, followed by a panic attack and tears. This is how their summer trips to Brooksville would end, but it’s not how they would begin. They were blissful trips, marked by hikes, swimming, and quiet.

Like most young professionals, big cities like New York were the epicenter of their social and professional lives. They had a tight-knit group of friends, went to concerts, ate at great restaurants, frequented museums. And they were thriving in their careers, Julia in marketing and Dan in advertising. But their days were defined by long commutes to and from work, and the act of chasing after free time was a drain in and of itself. Getaways outside of the city for hiking, rockclimbing, or kayaking required a lot of effort—and a lot of money. Their trips to Brooksville always offered a welcome reprieve.

“When you have these really intense emotional reactions to things the way we did whenever we crossed the border, that’s your intuition telling you to do something differently,” says Julia, a Bangor native. “When that feeling wouldn’t let up, it was obvious we had to change something.”

The couple, who have been together for 12 years, initially looked into moving to cities like Seattle and Austin, where jobs were likely more abundant—but they had their hearts set on Portland, which had everything they wanted out of a bigger city in a smaller, more manageable size. They watched it steadily transform over the years from being a nondescript collection of neighborhoods riddled with vacant storefronts to one that is a robust cultural outlet for Maine. But they worried that a move to Portland would stymie their careers.

“It’s not an easy place to continue a major city career path,” says Dan. “You have to approach your survival creatively. Sometimes that means maintaining a day job that has nothing to do with what you’re really passionate about and carving out time to keep doing what you love. A lot of people do that because it’s worth it to be here.”

But opportunities did come around. Shortly after Julia landed a job in the professional development program at Unum, Dan was recruited to join the renowned team at the Via Agency.

Fast forward three years, and the couple is happily settled in their West End home, where framed prints of Maine art and vintage maps of Portland adorn their walls. They have been taking lots of road trips ahead of the birth of their first child, due in July*. Paddleboards are perpetually strapped to the roof of their car, on the ready for their weekday routines, which for Dan consist of paddleboarding in Cape Elizabeth right before work. In addition to the wealth of options offered by Portland’s urban neighborhoods, they also enjoy getting out and exploring smaller Maine towns and cities.

“A lot of our New York-based friends thought we were committing social and cultural suicide by moving to Portland,” says Julia. “But now they come to visit and go to all the restaurants that are being written about in the New York Times. They see the quality of life here and they are drawn to it.”

That quality of life was the impetus for Sam Kilbreth and Old Port managing editor Jen DeRose’s exodus from the city as well. They had been flourishing in their respective professions. Kilbreth was a broadcast producer of commercials for clients and artists like Diet Coke, Chobani, Jay-Z, and Taylor Swift; DeRose was the digital director for the Hearst Design Group. Yet they found themselves craving a change of setting. More specifically, they wanted to live in a place that had all the virtues of a big city, but that would allow for easier getaways to the mountains and the ocean.

Finding that balance meant a great deal to the couple, whose passion for adventure has seen them backpacking in Southeast Asia and climbing Mount Kilimanjaro in Tanzania. Access to great skiing was important, too, especially for DeRose, who spent her post-college years skiing all along the East Coast and in the West, where she worked as the photo assistant for outdoor photographer Greg Von Doersten.

“We talked about moving to cities like San Francisco and Seattle,” says Kilbreth, who was raised in Brunswick and Portland. “But we also talked a lot about Portland.”

Portland held many special memories for the couple. It’s where they spent many holidays, and it was also the setting for their wedding, for which the couple commissioned a ferry boat to shuttle guests from Portland to the ceremony on Birch Island. They held their reception back at the Portland Company Complex, where the venue’s rustic, wooden beams and views of docked boats gave guests a special taste of Maine. “I wanted to get married outdoors in a setting that we could go back to and that felt personal—not anonymous,” says DeRose. “Sam always imagined getting married on the rocky coast of Maine, so this was perfect. That night, we slept on a boat docked in the harbor.”

Portland felt like the right fit, but without the right jobs, it was a far-fetched notion. Lucky for them, the editors at Maine Media Collective—which publishes Maine magazine and Maine Home + Design—were brewing plans for a third publication, Old Port. DeRose happened to reach out at exactly the right time and landed a job as the nascent magazine’s managing editor. The couple, who have been married for two years and together for almost ten years, made the move to the West End this past spring.

“There is an emphasis on home and on having a life and spending time together that is much stronger here. You have time to walk around and actually experience the place in which you live,” says Kilbreth. “In New York, you’re just trying to survive. You don’t have any literal or figurative space to think or exist or even breathe.”

DeRose’s new role at Old Port magazine has kept her on her toes, yet it’s a brand of busy that has enriched her experience of Maine, rather than hindered it. In a way, it has provided her with a fast track to being better acquainted with the city’s culture. She has overseen photo shoots at establishments like Fore Street and the Top of the East Lounge, attended numerous charity-minded events like the Kennebunkport Festival, traveled on assignment for Maine magazine’s 48 Hours column, and scouted homes for Maine Home+Design. Meanwhile, Kilbreth has been freelancing for Boston-based marketing and technology firm DigitasLBi, where he’s currently at work on advertising campaigns for auto and athletic wear companies.

Apart from their work lives, the two have been navigating a new sense of normal. Their pace has been a slower, more explorative one, and they have reveled in the opportunity to see facets of Portland beyond the surface impressions that make it a charming city to visit. “There is a friendliness in Portland that doesn’t exist in New York because of the city’s size,” says DeRose. “You are able to feel really connected, and you see this fabric here—the way people are woven together and the way that everyone overlaps in day-to-day life.” Kilbreth adds, “It feels like we’ve gotten a whole new lease on life.”

That connectivity was partly what attracted Andrew and Briana Volk, owners of the year-old Portland Hunt and Alpine Club, a sleek Scandinavian-influenced craft cocktail bar located downtown. After many years of living in Briana’s native Oregon (more precisely, the other Portland) and after a stint in Mobile, Alabama, the couple was ready for something new—something smaller than Portland, Oregon, but just as culturally vibrant.

“Portland’s got a lot going for it,” says Andrew. “There are all sorts of little pockets that contribute to a larger sense of this creative community: phenomenal food, wonderful art, access to larger cities.”

In some ways, Portland is reminiscent of European cities, its walkability and its various gathering places—places like coffeeshops and bars—contributing to what Dan Bailin calls “the Sesame Street feel.”

“We have this joke that Portland has so much going on, yet on any given Saturday or Sunday it can sometimes feel like Sesame Street,” says Dan. “You’ll sit down at Sonny’s and the guy sitting two bar stools down is someone you’ve never met but you recognize him from a show you went to recently. That same day you’ll run into him a few more times, maybe even with another group of people you know. It’s just small enough that it still feels like a neighborhood, and so many places here feed into that feeling. Portland Hunt and Alpine Club is definitely one of those places.”

This was the goal and hope when the Volks opened their bar: to create a hub that combined all the great aspects of their favorite haunts in every city they’ve lived in. “In our little world of food and restaurants, the support that the community gives to each other—whether you’re someone who is struggling or doing something new—it’s a rare and special thing,” says Briana, who was a writer at the Via Agency for two years before opening the bar with Andrew.

Andrew, whose history in mixology has been punctuated by numerous accolades (including a James Beard Award nomination), was no stranger to Maine. A Vermont native who graduated from Colby College in Waterville, he spent some time living in different Maine towns and was always drawn to the idea of putting down roots in the Pine Tree State. He loved the landscape, but mostly he loved the people—their unique sense of character, their authenticity, their honesty.

“People don’t put on airs here. You know exactly where you stand,” says Andrew. “If somebody likes you, or if they don’t like you, you know it. To me, that characterizes both northern New Englanders as well as Portlanders.”

When they talk about Portland, and all the things they love about Maine, each couple inevitably returns to the connection to family. For the Volks, this includes their five-month-old daughter Oona.

“When you grow up here like I did, you always have this desire to get out and see what the rest of the world is all about,” says Sam Kilbreth. “You discover pretty quickly that it was a pretty great upbringing and that Maine is a special and unique place.”

Julia jokes that if they happen to be out of town while she is in labor, she plans to drive as fast as possible to the Maine border. “I want my kids to be Mainers, and to have the kind of upbringing I had in Bangor,” says Julia. “I want them to know what it’s like to have a city experience as well as one where hiking, camping, and fishing are part of their lives.”

It is, after all, the way life should be.

*Congratulations to the Bailins, who welcomed their newborn, Penelope, as this issue was going to press.

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