Upper School

College Counseling

Where the journey leads

Families don't choose Highland for one great year. They choose it for where the journey leads. For most, that means the right college. College counseling is where years of growth come together in a plan as individual as your child.

This isn't a senior-year scramble. It's a four-year partnership between counselors, students, and families that starts in ninth grade and ends with a confident answer to the biggest question of all: Where do I belong next?

Built around your child

The college search shouldn't feel cookie-cutter. At Highland, it never does. Our counselors work directly with every student and family to find each student's true "best fit" academically, socially, and personally. No single formula. No one-size-fits-all list. Just counselors who know your child by name and guide every decision along the way.

That work is led by a dedicated team. Megan Catalfamo, Director of College Counseling, partners with Bridget Doyle, Assistant College Counselor and Testing Coordinator, to give every family focused, personal guidance from the first conversation to the final decision.

We don't help students find a college. We help them find the right one.

Four years, not four months

Most schools start the conversation late. We start it the moment students enter the Upper School. Check out the expanding boxes below to learn more about college counseling for students through each year:

Meet Our Team

List of 2 members.

Megan Catalfamo

Director of College Counseling
Bridget Doyle

Freshman Dean, Assistant College Counselor, Testing Coordinator

College Counseling

List of 4 items.

Freshman Year

College counseling at Highland begins in 9th grade with Freshman Seminar, led by our Freshman Dean. Designed to support a smooth academic, extracurricular, and social transition to Upper School, the course empowers students to build strong academic habits, engage in campus life, and actively nurture their unique interests and talents. In the spring, students meet one-on-one with their Dean for personalized academic advising to craft their sophomore year course path. Complementing this work, our Director of College Counseling leads interactive sessions focused on maximizing the Highland experience—helping freshmen understand how the skills they hone, the relationships they build, and the values they demonstrate today naturally begin to shape their authentic story for college applications down the road.
Sophomore Year

In 10th grade, college counseling transitions from laying strong habits to intentional self-discovery and practical preparation. Through Sophomore Seminar, counseling staff visit classes regularly to guide students through SCOIR, Highland’s college planning platform, and facilitate the PrinciplesYou career assessment to help students align their personal strengths with potential path choices. During the school day, sophomores sit for both the PSAT in October and the PreACT in February, with counselors providing individual guidance to translate those results into tailored testing plans. Spring brings tangible exploration: students visit a variety of campus environments on the College Sampler Tour, attend the Middleburg College Fair & Preview Night, and partner with counselors for ongoing academic advising—whether selecting junior coursework, pursuing leadership opportunities, or applying for competitive summer enrichment programs.
Junior Year

Junior year marks the launch of a deeply personalized, one-on-one application journey, kicked off in November with a dedicated family workshop featuring guest college admission professionals. Throughout the second, third, and fourth quarters, students meet weekly in Junior Seminar to navigate every facet of the search—from evaluating right-fit institutions and drafting compelling essays to analyzing standardized testing strategy following October’s PSAT/NMSQT. Every family completes an individual Junior Family College Counseling Appointment to build a customized post-secondary roadmap. That strategic planning extends into real-world career discovery in March, when students complete a three-day Junior Internship arranged with counseling support, followed by direct networking with admissions representatives at the Middleburg College Fair in April. The year concludes with one-on-one academic advising to finalize senior schedules, verify graduation requirements, and ensure each student enters senior fall with clarity, confidence, and momentum.
Senior Year

Senior year brings the entire process to fruition as students take ownership of their post-secondary plans with step-by-step guidance. The year begins in September with a Senior College Planning Event for families, providing a strategic overview of application deadlines, financial aid, and current admission trends. Throughout the first semester, Senior Seminar meets regularly to help students finalize their college lists, polish application materials, craft authentic essays, and manage specific requirements for specialized programs or scholarships. Once applications are submitted, second-semester seminar shifts focus toward life beyond Highland: students design their immersive Senior Projects and participate in practical transition workshops covering college course registration, housing, campus safety, and self-advocacy. By blending tactical application support with real-world transition planning, Highland ensures seniors graduate fully prepared to step onto campus with confidence and purpose.

Real experience shapes real choices

Highland students don't guess about their future. They test it. Through the Junior Internship, students step into real workplaces to discover what a career actually demands. That leads into the Senior Project, where seniors spend two weeks pursuing a career, academic, or service interest in depth. Then, they present what they learned.

These experiences sharpen the search. Students stop wondering what they might want and start choosing based on what they've lived. They arrive at applications with conviction, not questions.

Counselors connected to the field

Great counseling depends on staying current. Our counselors hold active memberships in the leading regional and national organizations, including NACAC, PCACAC, ACCIS, the College Board, and DCCA.

Those connections keep our team plugged into how admissions really works today so your family's guidance always reflects the present, not the past.

See it for yourself

The best way to understand our approach is to meet the people behind it. Come visit, talk with our counselors, and see how we help every student find the college that fits. The journey matters. This is where it leads.