Five Fifty-Five

  • Steak and truffle fries with Parmesan-Reggiano aioli, Five Fifty-Five style.

  • Five Fifty-Five owners Michelle and Steve Corry with chef Kyle Robinson, left, who has taken over most of the cooking duties.

  • In addition to an award-winning wine list, inventive cocktails include the Basil Smash.

  • The private dining room on the third floor can be arranged to suit a variety of gatherings, from rehearsal dinners to corporate meetings

  • New England scallops have been a menu favorite from the beginning; the preparation changes with the seasons.

For special occasions or everyday dining, this city landmark strives to be better every year.

Fifteen years ago, Michelle and Steve Corry were among the first wave of restaurant-owner couples to elevate the level of dining in Portland. As the city’s restaurant scene was beginning its ascent, they opened Five Fifty-Five, serving sophisticated American cuisine with finesse and providing exceptional service. Chef Steve Corry offered breakthrough dishes such as truffled lobster mac and cheese, combining Maine’s finest resource with a beloved comfort food. That dish and others, including his mussels with roasted garlic and pickled cherry peppers, and grilled Caesar salad, became signatures at Five Fifty-Five, attracting diners in search of originality and flavor. Over the following decade, dish by dish, the Corrys built a solid reputation and loyal customer base.

Steve Corry rarely works on the line at Five Fifty-Five any longer, choosing to spend most days at home with the couple’s two young sons. Chef de cuisine Kyle Robinson now heads up the tiny, open kitchen, and Michelle is grateful. “Hiring Kyle made a difference in our lifestyle,” she says. “It took Steve about six months to loosen the reins, but we trust Kyle fully. He and Steve are very similar,” Michelle continues. “They’re both pretty calm and mellow. It was a good transition, very respectful of each other.” Robinson, a Maine native, came to Five Fifty- Five from the Little Nell, a luxury resort in Aspen. He was ready to make the switch to a small, independent restaurant, and be closer to his family. Like Steve, Robinson is “fiercely seasonal,” adding and subtracting menu items according to what tastes and looks best right now. “I won’t touch the old favorites that Steve created,” he says. “But the seasons are so short here, we have to jump on using the ingredients immediately.”

Last fall, the two chefs had some intense discussions about how to freshen up the menu while maintaining the restaurant’s identity. “We just wanted to make it more fun and casual,” Robinson says. Small plates were added, showcasing the best of each season with salads, pasta dishes, and seafood snacks, such as scallop ceviche and sockeye salmon rillettes. A summery bowl of chilled English pea and coconut soup with Maine crab, spiked with pickled carrots, was a recent feature. “We try to use flavors that are comfortable and approachable, but with our own touch,” says the chef. The five-course Signature Tasting menu is a delicious opportunity to taste both old favorites and seasonal additions, with the offerings changing frequently. When Robinson joined Five Fifty-Five, his wife, Yazmin Saraya, came along as well. The pastry chef has been a stellar addition to the team, contributing wildly creative, sophisticated desserts. They are as seasonal as the rest of the menu, making excellent use of local ingredients, such as the berry sorbet with Greek yogurt semifreddo and blueberry meringue. Chocolate is well represented too, with offerings of “summer s’mores” and sea salt caramels. Saraya also bakes traditional French pastries for Petite Jacqueline, the Corrys’ French bistro in the Old Port.

These changes, and others, are part of the Corrys’ effort to remain relevant in an increasingly crowded Portland restaurant scene. “We try to make a change every year,” says Michelle. Two years ago, they renovated a third-floor loft-like space so that it can be used for private events, and the calendar has filled up with rehearsal dinners, birthday parties, corporate meetings, and holiday get-togethers.

The room has a stylish, industrial-chic look with copper wainscoting, heavily varnished rustic wood tables on casters—for flexible set- ups—and tall windows overlooking Congress Street. “I wish we had done this sooner,” says Michelle. “It’s used all the time.” This year, new tabletops made of ceramic tile with copper trim were installed in the main dining area, giving the room a more contemporary and casual look. While Five Fifty-Five is often considered to be

a special-occasion restaurant, the Corrys want diners to feel welcome at all times. “There’s no dress code,” says Michelle. “No pretension.” Some choose to dine in the comfortable bar area, where the entire menu is available.

The atmosphere may feel more relaxed than ever before, but the high level of service has not changed one bit. Before coming to Maine, Michelle Corry worked at the world-renowned French Laundry restaurant in Napa Valley. She trains the staff to serve with skill, knowledge, and warmth. “We run it like a fine-dining establishment. If you work for me for a year, you can work anywhere in the world,” she says.

Like the dining experience, the wine list has a full variety of options, at a wide range of price points. “People in the Northeast are price- conscious,” Michelle says. “We’re very cognizant of that.” Michelle has worked hard to bring the wine program to the next level, with a focus on staff training, earning the restaurant a Wine Spectator Best of Award of Excellence title. The list is heavy on California and French labels, a good match for Robinson’s menu.

“Fifteen years went by in a hot second,” says Michelle. “The city has changed so much.” But Five Fifty-Five has built a dedicated following, and with a constant refresh, is very much in the game.


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