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Amy Kirkcaldy

Associate Director of College Counseling
Grade 6 Spanish Faculty

Joined Milton in 2012

amy-kirkcaldyFor a long time, we had heard from a respected colleague about this cracker-jack admission officer from Harvard, who read student applicants astutely and deeply, who could find the fairest course of action in even the most complicated financial aid cases, and who through it all maintained a refreshingly irreverent sense of humor and a balanced perspective. So, when Amy Kirkcaldy’s resume appeared in a job search, we jumped.

In the intervening years we have discovered that Ms. Kirkcaldy is all that our colleague had promised and so much more. After graduating from Harvard, Ms. Kirkcaldy taught English at the Tec de Monterrey and did freelance writing for Fodor’s Mexico. Back in the U.S., Ms. Kirkcaldy next coordinated the MIT-Mexico internship program and then taught Spanish at Duxbury High School before heading off for four years as an admission officer in Harvard’s admission office.

Here at Milton, Ms. Kirkcaldy has also put her distinctive stamp on the community. In addition to her college counseling duties, she has taught Spanish in our Middle School, served on our campus-wide Wellness Committee and our Class IV Committee (charged with rethinking the ninth-grade experience at Milton), and taught sections of Senior Transitions for our affective education program. Most recently, Ms. Kirkcaldy has been serving as mentor in Milton’s mentoring program for new faculty, and she has co-founded and now leads AWARE (Alliance of White Anti-Racist Educators).

Outside of Milton, Ms. Kirkcaldy has led admission and financial aid workshops for community-based organizations and the College Board, and has volunteered as a college counselor at the National Association for College Admission Counseling college fair in Boston. In her free time, she enjoys gardening, cooking, running, and exploring Massachusetts with her husband and twin boys.


B.A. in history, Harvard College
M.Ed and Massachusetts Initial Certification in foreign language, Fitchburg State University


Financial aid was essential in in my own college process. Gratitude for the aid that was awarded me drove me to work in financial aid as a college student and, later, as a professional. At Milton, the highlight of my work is helping all students find college options that fit who they are and who they hope to be, and helping students for whom college cost is a real factor find affordable options that will lead to financial freedom and open doors after graduation, not crushing debt. I am happy to help students and families with every step of the process, from filling out the FAFSA and CSS Profile to comparing financial aid packages, to requesting a reconsideration of aid, to financing.
Amy Kirkcaldy

Associate Director of College Counseling