Yesterday was the first day of school.

Depending on who you are, you might read that sentence differently. For many, there’s an exclamation mark at the end. It was a day filled with excitement–new things to learn, a chance to welcome back students to the classroom, kids actively learning rather than doing ‘maintenance’ work of quarantine months gone by.

For others, (like a certain teen we know) the statement means an end to summer vacation and actually might be said best with an eye-roll.

And for some, the line might read as a statement of frustration, sadness, or worse. Yesterday didn’t look like any first day of school we’ve ever seen before. No parents taking first-day-of-school photos at bus stops. No buses dropping off kids in shiny new outfits and sneakers at the front door of school buildings, to teachers waiting in actual classrooms. No cafeteria lines. No school bells.

For the Wilton Public School community, which started off the year with a remote learning plan, it was a day of students sitting at home in front of computer screens, with teachers in empty classrooms peering back at them through a computer camera. For some, the experience of technologically-enhanced remote learning worked well; for others, not so much.

Superintendent Kevin Smith, who one might imagine could have been a wee bit stressed anticipating the day, probably said that line with a huge sigh of relief–mixed with a shot of reality.

“All in all a very good day,” he texted GMW well after most of Wilton had gone to bed. “By far the highlight was students and teachers reconnecting. Not a perfect day and it sounds like we may have had a few families that found some of the tech issues insurmountable.”

He acknowledged the difficulties some families had with the technology that was critical for the school day to actually proceed.

“Definitely a range of tech issues added some stress to the day. Access to Zoom and access to Schoology was episodically problematic. We are actively working to respond to all of the issues we are aware of and hope that the week gets smoother for everybody as it progresses.”

Lots of Zoom calls worked, others didn’t. There was even some Zoom-bombing at the high school. Some students easily adapted to learning by computer, others had more difficulty. So too did some teachers easily adapt to teaching by computer, while others struggled. Other students were surprised when teachers they expected to see weren’t on the other end of the computer connection–and emails shared that some faculty had unexpectedly taken leaves of absence, and the search was on for a long-term substitute (see email below).

We put out a call to the school community to tell us how the first day went. Underscoring that it was just the first day, we’re sharing their thoughts (and can add to it for anyone who still wants to add their experience–email us at Here’s what these administrators, teachers, and families told us:

Editor’s note:  some contributors asked that their names be withheld.


Kathy Coon, Miller-Driscoll School:  “The first day of school at Miller-Driscoll was a HUGE success! I could not be more proud of the entire Miller-Driscoll community! Students spent time in Zoom sessions meeting their classroom teacher, getting to know each other, and meeting the other teachers and staff who will work with them this year. Teachers greeted their students with stories about themselves, props, picture books, and fun activities to keep the kids engaged, and many opportunities for interaction. Parents supported their children throughout the shortened day with technology and the materials needed to complete the day one activities–not to mention many words of encouragement! It took a village, the village stepped up and the 2020-21 school year is underway!”

Jory Higgins, Middlebrook Middle School:  “Teachers and faculty were so excited to welcome students back and felt that excitement come back to them from the students. Obviously the computer screens are not the same as seeing students in person, but the students and staff started making wonderful connections. I was able to jump into a few classes to wave and say hello to many smiling faces and I was able to hear the connections being made.

“As may be expected there were issues with technology. Most were connectivity issues that were resolved with a refresher to families on directions “how to” that were included in many letters home and on the website. We had staff fielding those requests throughout the day and as the day wore on there were fewer to answer.

“We’re so proud of the resilience demonstrated by our staff and students knowing nobody wanted to go to school this way, but they forged on and made the very best of it.”

Bob O’Donnell, Wilton High School:  “At Wilton High School our faculty was very excited to see the students back to school, albeit in our virtual learning environment. Seeing the students, hearing some of their funny summer stories, and learning with them made the challenging work of the last few weeks very much worth it. As teachers, it is our calling to work with students and help them learn. This had been missing during the past two weeks. All of our advisories engaged with the students on some connectedness activities, Schoology training, and learning about health and safety protocols in the building. Some of our student leaders produced PSA’s on building safety protocols which were engaging for the students. Our staff continues to pull together to learn and, ultimately, move toward mastery of the new technology, which will continue to take some time. During the past few years, we have hired some newer teachers who are quite tech-savvy and it is nice to witness them taking a leadership role in professional learning with their colleagues. It was a rewarding day because of the student engagement aspect and we are looking forward to building upon this during the rest of the week.”

Jen Falcone, Cider Mill School:  “Today was a unique, but amazing first day of school at Cider Mill. I am grateful for our extraordinary staff. They spent the day engaged in various activities designed to build community among their new students to help new classmates get to know each other. Throughout the day, students navigated a variety of technology platforms including Zoom and Schoology. Every time I walked into a room, it was filled with the laughter and joy of being back together again. Teachers used productive problem-solving skills and a lot of collaboration when staff encountered a tech glitch or when students needed support from home. We celebrated the end of day with more smiles thanks to our friends at College Creamery–there’s no better way to celebrate the first day of school than with ice cream! A special thank you [from administrators and CM PTA] to our [teacher] family community who extended grace, kindness and support throughout the entire day–thank you! #togetherisbetter. We are looking forward to a fantastic 2020-21 School Year.”

Email from WHS Associate Principal Don Schels about Teacher Leave of Absence:

Dear Students and Parents:

Welcome to the start of a brand new school year! There is no blinking at the fact that this year is very different, with lots of extra concerns and things for us to be mindful of in order to be safe and successful. Despite the additional challenges, teacher and staff excitement at the prospect of finally seeing students again is palpable.

I am writing to inform you about the way you will engage with some of your classes. In a few cases, teachers are on leave and will not be able to start their courses. We are close to hiring long term replacements for these cases, but some remain unfilled. You are currently enrolled in the following course or courses which will be covered by a substitute teacher during the first week of school:


Although our substitutes can be very helpful, they are not yet ready to broadcast live in the teacher’s stead. When this/these course(s) meets, during this first week of remote learning, please log into Schoology and follow the directions that have been loaded for you. The idea will be to complete some activities (the same ones that will be happening in other classes during the period in question) that help make you more comfortable with your return to school. Even though you will complete this activity asynchronously, it is very important and will be reviewed live very soon when the teacher assignment is filled. Again, best wishes for a safe and productive school year.


WHS teacher:  “It was immensely gratifying and exciting to meet students today! Even though the Zoom format is a little awkward, the students were smiling and engaged. My classroom still needs some tech hardware, and I have to admit I’m still bumbling a little with Zoom, screen sharing, and Schoology. Overall, I thought it was a pretty successful day, and I’m grateful to have the extra time during the afternoons to fine-tune my use of technology and Schoology.”

Middlebrook teacher:  “It was EXHAUSTING!! The main reason was because of the Zoom exhaustion. I could see it in my students’ faces and eyes that it was simply too much screen time and this was a shortened day where there wasn’t new learning taking place but getting to know one another. I find it difficult to support a hybrid model where a teacher should be live with remote students and in-class students. It is not feasible!! I have sat in on several Zoom hybrid practice classrooms and the people who are remote are clearly disconnected due to lack of ability to hear others, waiting for a turn to speak, and ongoing technology garbling when people are speaking. It is not a good solution to Zoom and be live and teach in-class students. I propose that on days students are remote they take their lesson from Schoology. I would also like the Zoom to be used as check-in for attendance and instruction at [the] beginning of class for remote and in-person learning. At that point, Zoom should be optional, not a must-have tool to teach; it’s just not practical and the loss of instruction due to fatigue and technology disconnect will rapidly affect the deterioration of learning. So bottom line, Zoom is not the answer. Exhausting! Zoom Fatigue! Only day one, a half-day.”


Donna Peterson:  “I loved how people treated this like a real first day with first day of school photos of their kids posted on Facebook and many people posted their children’s unique workspaces. There were thank you notes and well wishes for the teachers too. It really felt like a community. Like we are all in this together and everything will be okay.  This sentiment helped to normalize the situation. It also provides a great example for our children in adapting well to any situation. Once again, I am thankful and proud to live in Wilton.”

Dana Haddox-Wright:  “I have a 3rd and 5th grader who made it through without any problems. It was comforting, hearing how happy the kids on the other end of the Zoom meetings happily greeted my kids and their other classmates. The teachers were amazing at keeping my kids engaged. All in all, I’d say kudos to everyone for adapting so quickly during this crazy time.”

Anonymous WHS Parent:  “I’m disappointed that we just learned today that my child’s biology teacher at the high school decided not to return. I completely understand that teachers had some difficult decisions to make, but from the students’ perspective, it’s not an ideal way to start one’s high school experience, especially such an important and challenging class. Both of my WHS kids said that some teachers had a better understanding of Schoology than others. One teacher said he had no idea how to use it and to email him their assignments for now. My kids said it was terrific seeing their friends, even though it was online. All in all, not a bad first day of school.”

Marie Demasi:  “I have to admit I didn’t sleep last night I was scared today would not go as smooth as it did! But I am happy to report 3/3 SUCCESSFUL FIRST DAYS!!! Twins in 5th were happy and engaged!! My son was on camera–this didn’t happen in spring!! To see them both share their day right after, full of giggles and excitement, what they liked and didn’t and both love their teachers!!! My second grader was on camera the whole time, actually had me come assist when she couldn’t see the Zoom screen! And engaged!! She loved it and [her] first words were, ‘This is so much better than spring, I like that I can be with my teacher the whole time!!’

“So grateful for Mr. Scholz, Mr. Gallo and Ms. Howell for making today an amazing start to this new school year!!!

Anonymous Parent of two MB children:  “I am grateful for what is clear was a lot of hard work by teachers and others. But even the first glimpse of my kids and their dejected body language in front of screens was very sad and will be hard to forget. A short while ago many of the little ones were singing at a school concert, “Every night I lie in bed / The brightest colors fill my head / A million dreams are keeping me awake / I think of what the world could be / A vision of the one I see….”

“And now what of these dreams? What must our kids be thinking now? In a lot of ways, today felt like more of the same drudgery, after five months in which so much of what they care about has fallen apart, with very literally ‘no end in sight.’

As a parent, I applaud the educators and volunteers who are doing great work under impossible circumstances. But I pray we can find ways to make this situation better very soon.”

Suzanne Stocker:  “I just wanted to note that although this is not the most ideal learning situation (nor is it ever where I imagined we’d be as a mom of school-aged kids) it was very obvious how well the Wilton school teams collaborated on rolling out the new online teaching platform.

“Admittedly I was preparing myself for a day of technical issues (and whining kids to go with it) and, though I can’t speak for every student, my two logged in this morning and worked through the school day like they had been doing this for years.

“It took a huge load off to see how smoothly things went and for that, I wholeheartedly want to thank all the hard work that went into this.

“I’m sure a ton of planning and preparation took place behind the scenes to ensure things were as seamless as possible and I am incredibly appreciative of everyone involved to ensure the safety of the Wilton students. At the end of the day, we have amazing schools. It’s one of the many reasons why I love this town.”

Anonymous Kindergarten Parent

Dear Editor,

I’m sitting here not knowing whether I should cry, laugh, or just give in and pour myself a glass of wine. Yes, I know, it’s only 2:40 p.m., but you see…today was different than all the other days. Today was a whirlwind; a topsy turvy rollercoaster, today was filled with laughter, tears, frustration, excitement, and a whole lot of anxiety too.

What made today so different you ask? Today was our “first day back at school.”

My daughter had been looking forward to school for quite some time now and the thought of officially being a “big kid” – Kindergarten is a big deal, you know! With her being so excited to see and make new friends, to meet her new teacher, see the big kid school and be free from the semi-house arrest we’ve all been on since our friend “Rona” decided to visit the U.S., I rounded up every bit of courage I had to send my daughter back to school. With all the uncertainties, anxiety, and overall “Rona-mess” out there, I tried to prepare as much as I could have, but oh boy. Nothing could have prepared me for this.

We were a mere 10 minutes into our Zoom call of the day when she looked up at me and said “Mommy, can this be done now? Can I please go play? I want to color in and have fun instead.” I fought away my tears because I promised myself that #TeacherMommy will not fail her today, and here I am wondering if I was wrong to hope that everything would be okay.

I couldn’t help but feel as if I failed as a mom, as if I was punishing her by expecting her to sit still and listen to her teacher on the other side of the device she was streaming on. Having to reassure her over and over again that it’s going to be okay and that it’s almost recess time, that she just has to sit still and focus for a little while longer.

I could see her trying and she kept apologizing too, she also knew that this was not what she had in mind when she thought about ‘big’ school. I could see her mind wandering, I could see her daydreaming and I could see that she had no interest in participating in an online, remote class.

Can we face the reality that even though they are almost “big kids,” they are still little and not made for e-learning?

Teachers and schools have been trying their best to get everything as “normal” and comfortable as possible for our kiddos. I sat in awe as I heard teacher after teacher stay positive and reassure the kids. The teachers were trying their best to engage the kids, I could see they were really trying, they were all so kind, understanding, and patient. I will forever appreciate what they’ve done for us.

But, here I am, ugly crying. #thankyouRona

Our kids were asked to draw a picture to show how they were feeling about starting school. My kiddo drew a nice big smiley face, one that filled her whole page. I was so happy to see that, but after she showed it to the class and to her teachers, I saw there was another little face drawn on the other side of the paper.

A sad face.

I asked her why that face was sad when the other face was happy, and she said, “I saw the other kids were happy about school so I thought I had to be happy too.” My little girl, the one who couldn’t contain her excitement about starting Kindergarten, was no longer happy, nor excited. She was frustrated and sad.

Through her tears and frustration, she promised me that she would try her best tomorrow, and so did I. I promised her that I will try my best to help her when she feels overwhelmed and anxious. I promised her that I will try my best not to get frustrated at her for not focusing and getting distracted the whole time.

But most importantly, we promised each other that tomorrow we’ll try again. Today was different than all the other days, it was a whirlwind; a topsy turvy rollercoaster. But we’re clinging to the laughs, excitement, and hope that tomorrow will be better.

Yours Sincerely,

A Sad, but HOPEFUL, Kindergarten Mom

2 replies on “First Day of [Remote] School–How’d it Go, Wilton?”

  1. does anyone know if the internet connectivity issue at Comstock will be fixed for day 2 of school? my second grade son participates in the remote learning program, which is impossible to do without internet…for his first day of school, he could only participate in the morning zoom meeting.

  2. Heather, this article of yours is one for the ages… Kudos for painting a masterful picture of the day’s proceedings, from various angles. I’m sure it represents experiences being had these days around the world!

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