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About Our Program
Interested in learning more about our program? See below for information specific to your child’s grade at the time of application.
By joining Steppingstone, your student would receive up to 26 months of academic and social-emotional preparation for admission to challenging middle and high schools—plus support for years to come.
Please note: 4th grade Scholars and their families will be expected to apply to independent schools with Steppingstone's support.
Here's how it starts:
The Academy
A six-week summer program for two to three summers, beginning before 5th grade
For information about our full range of services through college graduation, visit our Program Overview.
By joining Steppingstone, your student would receive 14 months of academic and social-emotional preparation for admission to challenging middle and high schools—plus support for years to come.
Here's how it starts:
The Academy
A six-week summer program for two summers, beginning before 6th grade
For information about our full range of services through college graduation, visit our Program Overview.
Admission Process
Final Admission Decisions and Next Steps
Finalists will be notified if they have been accepted to the program in mid-April. Accepted Scholars will complete enrollment paperwork and attend the New Scholar and Family Welcome Event in May. Scholars begin their first Steppingstone summer in July.
Have questions?
The Admission team is here to help!
admissions@steppingstone.org | 617-423-6300 (press one for Admissions)
Hablamos español.
Jeniffer Castillo Gutierrez '12
Admission Associate
Jeniffer first joined Steppingstone in 2011 as a Scholar and commenced in 2012. She returned during her time at college as an Intern for College Success Academy between 2019-2021. Her passion for educational equity moved her to return again as Admissions Associate in 2025! Born and raised in East Boston, she is a proud Alumna of Boston Latin School. She received her B.A from Simmons University in 2023 with a major in psychology and minor in political science. In her role, she is excited to now work alongside Steppingstone to continue its mission. In her free time, she loves spending time with her family and friends, traveling, binge watching shows, and exploring Greater Boston!
Rachel Milambo
Director of Admission
Rachel joined Steppingstone in 2025 as the Director of Admission. She earned her Bachelor of Arts in Africana Studies and History from Bowdoin College and brings nearly a decade of experience in education. Throughout her career, Rachel has been deeply committed to advancing educational equity and expanding access to high-quality academic opportunities for students and families. In her role, Rachel looks forward to partnering with families and supporting them through every step of the admissions process, ensuring they feel informed, welcomed, and supported as they begin their journey with Steppingstone.
In her free time, Rachel enjoys spending time with her family, cooking, exploring new restaurants, and listening to podcasts.
Sofia Cabral '15
Admission Assistant
Born and raised in Dorchester, Sofia is a proud Bostonian and an alumna of Steppingstone’s class of 2015. Following her time with the program, she attended Dana Hall School and later earned her BBA in International Business, with a minor in Information Systems and Data Analytics, from Loyola University Maryland in 2026. The summer prior to joining the Steppingstone Admissions team, Sofia directed The Roxbury Youth Initiative, a branch of Harvard’s Phillips Brooks House Association’s Summer Urban Programs. Her passion for educational equity stems from her lived experiences, where she witnessed firsthand the discrepancies in educational quality between Boston Public Schools and private or exam schools. Sofia is excited to support Steppingstone’s recruitment efforts, ensuring that as many families as possible can access the exceptional opportunities the organization has to offer. In her free time, she enjoys going on walks, shopping, listening to music, and cooking.
Steppingstone is an educational nonprofit which serves students of various backgrounds. It does not discriminate in the administration of its educational policies, admission policies, scholarship programs or other organization-administered activities.
© Copyright 2026 Steppingstone Foundation, Inc.
