Matt and Aless met in 2011 in Bethel, CT at Matt’s second coffee shop job. Aless came in for open mic night, noticed the cute barista behind the bar, asked for his number, and… they have been inseparable ever since. Pretty early on, the two began mentioning the idea of opening a coffee shop one day.


After both working in coffee in southern Connecticut for the next year or so, they moved to Boston in 2013. There, Aless attended LUCAD to study visual art, and the two immersed themselves in the Boston/Cambridge coffee community. Matt began working at Simon’s Coffee Shop in Cambridge, where Aless eventually joined him to leave the corporate coffee scene and cut her teeth in the specialty realm.

At Simon’s, the two learned how to taste coffee, dial in espresso, steam milk correctly, and how to work in a busy neighborhood shop that serves the local community and churns out the good stuff. They also made friends with some incredible baristas, whom they learned from, grew alongside, and even lived in an all-barista house with. They started getting involved with expanding their own reach within the scene, by attending events like latte art throw-downs and with Matt spearheading a guest roaster program at Simon’s. It was time for new endeavors.

First, they eloped. And then, Matt went on to help open Kohi Coffee in Brighton and then in downtown Boston, as the quality control manger and events organizer, and provided training to baristas. At the same time, Aless moved on to work at Google Cambridge’s coffee bar, where she worked in a high-volume environment, perfected her latte art skills, and taught classes on espresso and manual coffee brewing. The two became more involved in the coffee community, attending discussions, latte art throw-downs, and even leading cuppings.


While living in Boston, the dream of opening their own coffee shop someday became solidified, and they knew they had to learn more about coffee and coffee culture in the rest of the world. In 2017, Aless went to Italy, the birthplace of espresso, and travelled from Bologna to Rome to Naples, drinking espresso and observing the culture of coffee there. She met up with Matt in Berlin, then Stockholm, and then London and Brighton, England. They went from shop to shop, experiencing the culture, tasting different shots of espresso, manual brews, and espresso drinks, and observing the differences in flavor, atmosphere, and asking questions to baristas as they went. They returned to Brighton, England again in 2018 to visit family and explored even further the coffee culture there.


In 2018, Matt and Aless decided to seriously start looking for locations for the shop. Middlebury was the obvious choice, as they had been visiting Matt’s mother there for the past six years. They fell in love with the town, the pace, the gorgeous landscape, the kind people, and the sense of community. They decided it would be a great spot to settle, open up shop, and eventually start a family.

They found the location at 30 Seymour Street in late 2018, and signed the lease as soon as possible, beginning the buildout in early 2019, and finalizing the business plan. After a few months of planning, deciding which other companies to join forces with, creating a menu inspired by their years of experience, travel, passion, hard work, and dreaming, Royal Oak Coffee is opening its doors on May 1st, 2019.

The name Royal Oak Coffee is in honor of Aless’ late father, Dave, whose business had been named Royal Oak, and who was a coffee lover himself.


Matthew Delia-Lobo

Co-Owner, Barista


Alessandra Delia-Lobo

Co-Owner, Barista