Laying a Foundation of Self-assuredness at Landmark Preschool

By Landmark Preschool September 7, 2022

The passage from preschool to kindergarten can be a daunting milestone for children, marking the start of a lifelong journey in formal learning. Landmark Preschool, Ridgefield Academy’s preschool affiliate, strives to ensure that their graduates are confident and independent when they walk into kindergarten for the first time with their crisp backpacks and bevies of school supplies.

“We start from day one to prepare our students for the transition,” said Evelyn Tangney, Director and Head Teacher at Landmark Preschool’s Bedford, NY campus. The basis for kindergarten readiness is confidence according to Tangney, and Landmark Preschool’s teachers work to build self-assurance “as soon as possible.”

Landmark Preschool operates three campuses: a half-day program in Bedford, NY, a full day program in Westport, CT, and a full day program in Ridgefield, CT. Each Landmark Preschool campus shares the belief that children benefit from supported, joyful learning.

“We encourage our students to explore, to ask questions, to try things—just give it a shot. If you can’t do it today, you can try again tomorrow,” Tangney said.  Every day, the children are trying to figure out answers as they learn new social and fine motor skills. Science experiments provide an opportunity to understand that it’s okay to be right and to be wrong. In this way, mistakes become part of the growth mindset.

To further enhance student growth, each Landmark Preschool campus offers after school enrichment programs that provide students with the opportunity to socialize and engage with other children and take part in a variety of activities, including karate, drama, art, and more.

Preparing for Kindergarten

The pathway to kindergarten readiness is marked by a series of small but significant achievements that are acknowledged and validated by the Landmark Preschool staff. “It’s fluid; the milestones can be different for each child—social, emotional, academic or physiological,” Tangney said. “They may seem inconsequential to us, but they are huge to a child. Zipping a jacket, finding a cubby, or helping a friend are accomplishments that make children feel so good about themselves.”

Added Threes teacher Debbie Fink, “The pride in these tiny accomplishments and the ability to learn new skills leads to self-assuredness that extends outside the preschool walls. When children are confident and proud of themselves, they know how to navigate any situation that is new to them.”

Feeling comfortable about asking for help is a key factor in relieving some of the stress about entering kindergarten. According to Fours teacher Jen Bollaro, “We spend a lot of time building a trusting relationship with the students, so they feel comfortable seeking guidance from grown-ups. This is important because a lot of them are conflicted about kindergarten. We give them the message that it’s OK to be both scared, excited, and nervous. Toward the end of the school year, we read a lot of books addressing this theme.”

Landmark Preschool teachers also emphasize the positive and exciting aspects of kindergarten. Students understand they will have the opportunity to make new friends, explore on a new playground, and eat lunch in a different place.

Another cornerstone in kindergarten preparation and confidence building is strong relationships with parents. “We are a tight knit, loving community, and that transcends from staff to children to parents,” said Tangney. “We are in daily communication with our parents.” Teachers also send parents pictures and videos on a daily basis, whether it’s of the students making snow angels, finishing a sea creature puzzle, or playing grocery store.

Parents often reach out to faculty after their children move on to kindergarten, according to Tangney. “They give us very positive feedback about how well-prepared their children were for kindergarten.”

Deep bonds forged among parents, teachers, and students are at the core of the confidence that children develop at Landmark Preschool. “We all love what we do here—we are happy and smiling, and we are a strong family. We take care of each other,” said Fink.

Discover more about Landmark Preschool by scheduling a tour of the campus.

About Landmark Preschool

Landmark Preschool is an independent day school serving children ages 1-5. Affiliated with Ridgefield Academy, Landmark has three locations in Westport, Ridgefield, and Bedford, NY. The program at Landmark offers a joyful introduction to learning and nurtures each child as an individual. We believe that children are curious, capable, and ready to learn at an early age. A balance of structure and flexibility empowers children to explore the world around them and develop as individuals in a safe, secure environment. Landmark teachers are experts in early education and design dynamic learning experiences to support social, emotional, cognitive, and physical development. Character building and respect for others are integrated as essential components of each day. A low student-to-teacher ratio establishes warm, personal connections and helps teachers find the optimal way to support each child during these all-important first five years. For more info visit