As the school year starts up in the middle of the pandemic, the town of East Hampton, Long Island is getting ready to welcome new faces in their classrooms. 
"There's probably about 20 houses on my street," said East Hampton Union Free District school board president James Foster. "On a normal day, in say February, March, there might be six houses that are occupied. This March, I think there was maybe one house that wasn't occupied." 
His district fielded 150 inquiries from parents interested in enrolling their students in the public school system this year, which could mean as much as a 10 percent increase in overall enrollment. As of mid-August, 40 students were formally enrolled, but many of its schools were not requiring official commitments until the first day.
The uptick is also pronounced at East Hampton's private schools. The Ross School saw its student body increase 11 percent despite limiting classroom sizes and cutting down on boarding students. Elementary students more than doubled. Meanwhile, Avenues: The World School has also established an East Hampton location to accommodate more children in the area. 
"I think families believe we probably have a better chance of being open and on campus in the fall," said The Ross School head of advancement and operations Andi O'Hearn. "And they're very worried after the last stretch their kids have gone through that they need at least some in-classroom time."
Many families have fled cities to less crowded towns to find socially-distant places to live in the early days of the pandemic. Around 420,000 New York City residents left the Big Apple between March 1 and May 1, according to the New York Times. About 40 percent of residents in wealthy areas like SoHo and the Upper East Side moved elsewhere.
The phenomenon has been witnessed across the country. Colorado resort areas have seen boosts in second home purchases. Meanwhile, Vermont has also seen an influx of students.
The schools in these areas are facing a new dilemma. Remote learning has its challenges, and there are concerns students may fall behind, especially if they don't get fundamental skills, like reading, by a certain age.
"By first grade, we're hoping that kids are really learning how to read," East Hampton Union Free School District superintendent Richard Burns. "[If] you miss six months out of that, you're always going to be behind."
Parents aren't necessarily teachers, The Ross School's O'Hearn points out.
"I think it's very hard for parents of younger children, in particular," she said. "I know several people, one of them had to give up their job so that they could basically work with their children online with their teachers."
As things slowly open up and government aid dwindles, parents need to go to work. While East Hampton may seem like a place for the rich and glamorous, many of the public school students come from working-class families. About 45 percent qualify for free or reduced lunch, East Hampton's Burns pointed out. During the height of the pandemic, the district was handing out 300 free meals a day. 
"We have a lot of the worker bees," he said. "The families and parents who take care of the estates, which is a huge business. They're the folks that send their kids here."
Now more students means more bodies in classrooms, which makes social distancing more difficult. Additional resources like internet hotspots, computers, and financial aid for internet bills need to be figured out for remote learning. East Hampton school board president Foster said years of estate taxes have helped the district prepare for increased costs and they have the funds to help out those in need. The shutdown last year helped them prepare for what they needed to do this year. 
"No one can say that things don't have room for improvement, and I think that we are in that direction," he admitted. "But we're not perfect." 
To create a happy medium, the East Hampton public school district has decided to let families of elementary school students choose a fully in-person or fully remote learning plan. Middle and high school students will have in-person instruction two days a week, or can opt to remain at home. They estimated 20 percent would opt into full online learning, for a max of 17 students per classroom. 
"The biggest point for us was to give a choice," Foster explained. "I didn't say it was an easy choice, but at least you have a choice."
The Ross School is attempting in-person education five days a week. It's expanded its 63-acre campus to include an additional area for the lower grades. All classrooms have a designated outdoor area including tented mini-classrooms and students will be kept outside as much as possible, even if it means doubling up on coats in the cold weather.
"We are going to do everything in our power to be outside as much as we possibly can with the students," Andi O'Hearn said.
The private school comes with a price tag of $23,000 to $45,000 each year, but O'Hearn said the in-person instruction and the safety measures are worth the cost. 
"I think it's important to have, for socialization even, just within their pods, to be able to have a teacher," she noted.
Not everyone is convinced. Some parents like Samantha Fung feel the restrictions on what young kids can or can't do can hurt development.
"To not be able to hug their teacher, not be able to play with other kids, not be able to share supplies, I think that that can also be more damaging than just being at home," Fung said.
Ashly O'Shea is homeschooling her 9-year-old daughter, although she has a college-bound daughter who will be attending her freshman year in person. Many parents don't have the luxury of being able to teach their kids at home because they have to work to put food on the table, she pointed out.  O'Shea sympathizes with those who have to make the difficult choice. 
"Hopefully the communities can come together and find resolutions together to make it work where everybody's happy," she said. "But that takes open minds and open hearts and when you're worried about your own family it makes it hard to be empathetic to others."