Roby House August and September Happenings 2026

Oct 12

8 min read

The 2026-2027 school year is officially underway at The Roby House, and August and September gave us the kind of start every house hopes for: new faces, returning rhythms, full calendars, generous help from every direction, and a living room that now has a very well-timed new couch.

This year, Jake is holding down the role of lone senior in the house. He is joined by juniors Erick and Jayden, sophomore Darwin, better known around here as DR, and our newest program member, freshman Ca’Saun. We also welcomed two important additions to the household: our new Resident Tutor, Daven Palaez, a former ABC Scholar, DHHS graduate, and Boston College alum, and our new chef, Wynter.

Put that together, and we have the makings of a busy, lively, and very promising year.

The year begins with a full house

There is always a little adjustment period at the start of the school year. Bags get unpacked. Schedules get sorted. New routines take shape. Returning students remember what it feels like to be back together under one roof, and new students begin learning how the house works.

This year, that transition has felt especially smooth.

Jake enters the year as our senior, which brings a different kind of energy to the house. There is a quiet steadiness that comes with having only one senior. Jake knows the program, the school, the schedule, and the pace of life in The Roby House. That kind of presence matters, especially for younger students who are still finding their way.

Erick and Jayden return as juniors, bringing their own strengths, personalities, and momentum into the new year. DR is back as a sophomore, now with a year of experience behind him and a challenging academic load ahead. And then there is Ca’Saun, who arrived as our freshman newcomer and quickly made it difficult to believe he is new at all.

The house also began the year with important adult support in place. Daven Palaez joins as Resident Tutor, and his connection to the program makes his arrival especially meaningful. As a former ABC Scholar, DHHS graduate, and Boston College alum, Daven understands the experience from the inside. That perspective is hard to replace.

Wynter has also joined us as chef, and we are grateful to have her in the kitchen as the school year gets moving. A full house needs good meals, good routines, and people who help create a home base at the end of long days. Wynter is already part of that rhythm.

Ca’Saun settles in like he has been here for years

Every year, there is a moment when a new student starts to look less like “the new student” and simply becomes part of the house. For Ca’Saun, that moment came almost immediately.

He has acclimated to life at The Roby House so quickly that it would be easy to assume he has been here for years. The same seems true at school and on the football field. He has made fast friends with teammates and classmates, and he brings a warm, engaging personality into nearly every interaction. Whether he is with peers or adults, he has a way of connecting that feels natural and sincere.

Ca’Saun arrived a week early so he could begin the football season with the team. That early arrival was made possible because Laura, Peter, and Jake welcomed him into their home. Thank you to all three of them for helping make that transition smoother and for giving Ca’Saun a strong start before the full house reopened.

Those early days matter. Starting football before the school year begins can be a lot to take on, especially for a freshman entering a new school and a new living environment. Ca’Saun handled it with confidence, and he is already contributing to the Freshmen Football Team while continuing to learn his way around.

A few early arrivals made the start possible

Ca’Saun was not the only student who arrived before the official start. DR also came a week early for football workouts, and we are grateful to his host family, the Agovinos, for giving him a place to stay during that time.

Jake also made an early trip up for a night so he could be ready for the SATs the next day. Thank you to Jean and Rob for hosting him overnight and helping make that important weekend a little easier.

These are the kinds of details that can easily get lost in a busy season, but they make a real difference. A student needs a place to sleep before an early test. Another needs support getting to preseason workouts. A freshman needs a welcoming home before the full house opens. Again and again, the Roby House community steps in.

That support helped August move from a planning month into a real launch.

The house gets a refresh, and the garage starts a new chapter

When the guys returned, they were greeted by a new couch in the living room. Thank you, Jenn, for helping make that happen. A comfortable living room might sound like a small thing, but anyone who has spent time in a student house knows better. It becomes the place where people gather, talk, decompress, watch a game, laugh, and sometimes pretend they are going to start homework in five minutes.

We also found ourselves with more “stuff” in the garage, which means the garage is slowly being taken over as a game room. This feels like progress, though it does raise one pressing question: what should we call it?

A few early contenders have already surfaced.

Gamrage
Garame
The Garage Game Room
Something much better that someone has not suggested yet

Clearly, we are open to ideas.

Thank you also to Chad for all of his work in the house before the guys arrived. The weeks before move-in are full of tasks that often happen behind the scenes, but they set the tone for everything that follows. Walking into a house that is ready, organized, and cared for makes the return feel easier.

New goals are already taking shape

The early weeks of school always bring a mix of commitments, decisions, and fresh plans. This year is no exception.

Jake has started an internship at Yale New Haven Hospital, which is an exciting opportunity as he begins his senior year. Thank you to Aviva and Matt for transporting him weekly and helping make that commitment possible. Regular transportation support can be the difference between an opportunity being realistic or out of reach, and we are grateful.

Jayden is eagerly awaiting a telescope gifted by the Shoreline Astronomical Society. A huge thank you to the society for making that gift possible. It is always exciting when a student’s interest gets matched with a concrete tool, and a telescope opens up a whole sky of possibility. We are looking forward to seeing where that curiosity leads.

Erick continues to work on his fencing skills. Fencing takes discipline, patience, footwork, and focus, and it has been great to see him continue building in that area.

DR made a thoughtful decision about his schedule. Because he is carrying a heavy academic load, he has decided to focus there and step away from football for now. That kind of choice is not always easy, especially early in the year, but knowing when to shift focus is part of learning how to manage time, energy, and priorities.

Ca’Saun, meanwhile, is still finding his way around, but he is already making an impact. Between school, the house, and the Freshmen Football Team, he has jumped into the year with impressive ease.

Labor Day brought swimming, pizza, and a very good start to September

Labor Day gave everyone a chance to pause, enjoy the long weekend, and spend time together outside the school-day routine. Thank you to Steph and Gary for hosting us.

The guys loved the chance to swim and relax, and Gary’s homemade wood-fired pizza was a clear highlight. For the record, I loved it too.

Those gatherings matter because they give the students and adults around them time to connect without rushing from one obligation to the next. A meal, a swim, and a little unstructured time can do a lot at the start of a school year. It helps everyone settle in.

It also gave September a warm opening before the calendar filled up.

House Jeopardy makes rules and chores more fun

No school year starts without a refresher on house rules and chores. This year, we reviewed them through House Jeopardy, which is definitely more fun than a lecture and more memorable than a handout.

Thank you to Chris M. for keeping score and securing prizes for the winning team. This year’s winners were J Squared, Jake and Jayden, who are now on a two-year winning streak.

A two-year House Jeopardy streak may not come with a trophy yet, but it probably should. At minimum, it comes with bragging rights, and those are powerful currency in a house full of teenagers.

The game gave everyone a chance to review expectations, laugh a little, and start the year with a shared understanding of how the house runs. Chores, schedules, and rules work best when everyone knows what they are and why they matter. House Jeopardy helped make that happen.

September was full of visitors, orientations, and community

September brought a steady stream of events and visits, each one helping build the network that supports the students and the house.

On September 1, Chris, Steph, and Missy joined us for their specific orientations. Starting the year with clear communication helps everyone understand roles, expectations, and how to support the students well.

On September 9, Kate Patla joined us for dinner. Aside from the Patriots cake and jersey she wore, it was great to host her. 😊 Go Bills.

On September 11, we hosted the second annual host family game night. This has become a great way to bring people together early in the year. Games have a way of breaking the ice, creating conversation, and reminding everyone that community support can also be fun.

On September 14, we hosted host family orientation. Host families play such an important role in the student experience, and orientation helps set everyone up for a good year. The stronger the connection between the house and host families, the better the students are supported.

On September 24, we had a new internet and phone line installed. Thank you, Steve, not only for the upgrade, but for cutting the monthly expense in half while improving the service. Better service for less money is always welcome, especially in a house where homework, communication, and daily logistics all depend on reliable internet.

From September 25 to 27, we had our first host family weekend of the year. By all accounts, it was a success. These weekends give students a change of pace and help deepen relationships with the families who are part of their wider support system.

A strong start depends on many hands

The story of August and September is not just that the students returned, or that classes started, or that the calendar filled up. The bigger story is that many people helped make the start of the year work.

Laura, Peter, and Jake welcomed Ca’Saun early. The Agovinos hosted DR before the house opened. Jean and Rob gave Jake a place to stay before the SATs. Jenn helped bring a new couch into the living room. Chad worked on the house before move-in. Aviva and Matt are helping Jake get to his internship. The Shoreline Astronomical Society gifted Jayden a telescope. Steph and Gary hosted a Labor Day gathering. Chris M. helped make House Jeopardy happen. Steve improved the house internet while lowering the cost.

That is a lot of names, and each one represents a real act of care.

The Roby House August and September Happenings 2026 are a reminder that a strong school year is built by students, staff, host families, friends, volunteers, and supporters all doing their part. Some contributions are big and visible. Others are quiet and practical. All of them matter.

Looking ahead

Two months in, the house already feels settled, active, and ready for the year ahead. Jake is stepping through senior year with new responsibilities and opportunities. Erick, Jayden, and DR are each building their own paths. Ca’Saun has joined the house with warmth, confidence, and a quick sense of belonging. Daven and Wynter have become part of the daily rhythm.

The garage may or may not have a name yet. J Squared may or may not be beatable in House Jeopardy. The Bills and Patriots debate may not be settled anytime soon.

But the house is full, the year is moving, and the start has been a good one. Thank you to everyone who helped make August and September welcoming, steady, and successful. The foundation is set, and we are excited to see what the next months bring.