“When we took off? It was all a blur,” Kelsey said, laughing. “Sorry, I can only think of everything based off of when I had my children—but I know I was definitely pregnant then!”
Now almost six years—and two sons—later, it is impossible to tell that Kelsey and her husband opened their restaurant, Cutty’s, just months into new-parenthood. A framed cover of Boston Magazine hangs to the left of the 16-seat sandwich shop’s glass front door. Just above it radiates a neon, spray-painted silhouette of Food Network personality, Guy Fieri—adjacent to his autograph. A chalkboard wall extends the length of the restaurant’s right side which is home to a handwritten list of ingredients titled “where we get our stuff,” making ingredients like Taza chocolate and dutch-aged gouda more approachable. Paper menus with curling corners hang on the wall, just a glance above the open kitchen where sandwiches like the Ham Dijon, Greens Bacon, and Pork Fennel are assembled.
It’s a small space, but it’s lived-in and welcoming. The restaurant is customer-friendly and no-nonsense—just seats and sandwiches. It’s a space that celebrates the simplicity of a good meal in a comfortable setting, which is what prompted co-owners Rachel and Charles to open Cutty’s in 2010—for the love of food and through the frame of family.
“We are actually crazy and had a baby in July, but opened that February—so it was hard but great,” Kelsey said, smiling. “Our families are nearby so they helped out a lot.”
Although Rachel, a Needham, Mass. native, and Charles settled on their current Brookline Village location of Cutty’s after the permit for a food truck in Cambridge fell through, the pair isn’t unfamiliar with the local neighborhood.
Rachel grew up in a family with strong ties to Boston College as her father, two uncles, and multiple cousins were all Superfans. Although Rachel headed to New York rather than Chestnut Hill for school at the Culinary Institute of America, she met Charles while the two worked at Cook’s Illustrated magazine published by America’s Test Kitchen just a few blocks away from Cutty’s, in Brookline, Mass.
Kelsey noted that she has spent a lot of time in the food scene between restaurants and catering companies, but ultimately credits the pair’s career shift to the slowing publishing industry at the time. With both of their culinary experiences, the possibilities for their own restaurant were essentially endless, but they happily settled on sandwiches.
“Well, we do love sandwiches,” said Kelsey, laughing. “But there’s a whole thing that we’re able to do with a sandwich—like the meats we have on our menu are in some of the fanciest, most expensive restaurants in Boston where you might pay, what, over $20 for a charcuterie plate. Here we can put it on a really good sandwich and charge less than half that.”
From their in-house roasted beef to the variety of breads that are delivered daily from across the river in Cambridge, Rachel and Charles use the sandwich as more than just a vehicle for high-quality ingredients but celebrate the possibilities of one of the seemingly simplest types of cuisine.
Over the past few years Cutty’s has developed specials, like the Spicy Pork Tortas they feature on Tuesdays, but for the most part their standard menu has remained a constant. Although some of the specialty sandwiches they offer daily are overwhelmingly popular such as the Roast Beef 1000, made with crispy shallots, homemade dressing, and sharp cheddar on brioche, all of Cutty’s menu items share a similar backstory.
“Our menu just had a way of working out,” Kelsey said. “Like one day at a family lunch we had leftover beef and caramelized onions, and decided to make thousand island and that’s now the most popular sandwich. It all worked out like that—the house salad dressing is actually a recipe that my mom got from my aunt in the ’70s.”
The menu reflects not just what Rachel and Charles would want to eat, but what their friends and family eat and enjoy. Each sandwich is a story, a small anecdote or evidence of a shared meal. Each item an invitation to their combined culinary experience.
“Everything just happened like that, like that cookie,” Kelsey said, acknowledging the brown sugar treat that sat on a sliver of wax paper on the table in front of her, begging to be tasted. “It’s an old recipe of my husband’s, and so is the chocolate chip.”
Be it with Charles’ desserts or the new breakfast sandwiches that have recently made it to the menu, Cutty’s keeps people coming. A major lunch rush typically fills the quaint, corner location, and it is not uncommon for people to have to take their Spuckies and house-made potato chips to go. In the wake of their shop’s success, Rachel and Charles signed the lease on the property next door to their Washington St. location. This expansion plan was fueled by the couple’s savings and a kickstarter campaign that ran through October. The two intend to begin demolition this week and hopefully open the second half of the sandwich shop in January.
Although they plan on expanding their space by an additional 600 sq. ft., the Kelseys intend on maintaining the comfortable atmosphere that has characterized Cutty’s ambiance thus far. Much of the expansion will include more eating space and bright orange chairs, giving the pair even more opportunity to welcome the hungry clusters that come with success.
The noise of the sink silences, and an apron-clad employee walks past Kelsey to lock the front door. The last remnants of a chaotic lunch rush slip away as crumbs are swept off the floor. A slow silence begins to take over the small restaurant as things are put back into place, as the shop prepares for tomorrow’s crowd. Despite the sudden serenity, Rachel Kelsey still searches for an answer, for a timeline to explain her sandwich shop’s success.
“So my younger son is three, and I guess it was around right after we had him,” she said.
Although Kelsey can’t offer an answer as to why Cutty’s became so popular, her inability to think of her restaurant apart from her home life says it all. Cutty’s is completely intertwined with her family—from its menu developed out of shared meals and passed down recipes, to its timeline initiated by a marriage and characterized by birthdays. It’s comfortable and warm. That’s what makes Cutty’s so popular, what keeps people coming back—from menu to management, Cutty’s is a family affair.
Featured Images by Julia Hopkins / Heights Staff
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