My name is Dylan — a Middlebury College first-year (Class of 2029) originally from New York City, and I'm taking on new students this semester. I tutor English, ESL, French, AP US & European History, AP Government, SAT prep, college admissions essays, and math through pre-calculus. Here's what makes me different from the average college tutor: I graduated from Regis High School (NYC) in 2025 with a 1510 SAT score and hands-on tutoring experience — both through Regis's peer tutoring program and teaching ESL via Zoom at a UNHCR-funded school in Kuala Lumpur, Malaysia. Writing and college admissions are my specialty. I know firsthand how paralyzing writer's block can be during the college process — and I know how to fix it. I can help students structure their thinking, sharpen their supplemental essays, and approach admissions with confidence. French students, I've got you. Four years of high school French, a student exchange in Paris, and a genuine passion for language learning means I can help you move beyond memorization toward real fluency. I'm studying Economics with a minor in Chinese, and outside the classroom I serve as the student senator for the Class of 2029, volunteer at Charter House, and write for the Middlebury Campus newspaper. I take tutoring seriously — my goal isn't just to get you through the next test, but to build the kind of skills and confidence that stick.
Dylan works with students from the following schools:
Dylan offers in-person tutoring on or near the Middlebury College campus for families across Middlebury Vermont, Cornwall Vermont, Weybridge Vermont, New Haven Vermont, Addison County Vermont.
If you have a specific tutor in mind, you're welcome to request them directly — we'll confirm whether they're available and the right fit for your student. Otherwise, Ryan writes a personal email to understand your student's needs, learning style, and goals — then handpicks a tutor from the roster. You're not filling out a form and getting assigned randomly. If the first tutor isn't the right fit after the first session, we'll find you a better match at no extra charge.
Yes. Many families start with a single session to see how the tutor and student connect before committing to a regular schedule. There's no pressure to book in advance — reach out and we'll set something up.
Yes. Many of our tutors are strong across several subjects, and sessions can cover more than one if that's what the student needs that week. Flexibility is built into how we work.
Most of our tutors continue working through breaks, either online or in-person at the college if the tutors remain on campus during that vacation. We'll let you know in advance if a tutor has a gap in availability and arrange coverage with one of our other tutors — in-person or online — in the required subject.
Occasionally, if the student lives very close to the tutor's campus. Most sessions take place on or near the college campus or online. This keeps sessions in an academically focused environment — which tends to produce better results.
The families who see the biggest results are the ones who commit to a regular cadence — typically once, twice, or three times a week. One-on-one tutoring with a student from an elite college, who genuinely understands the material, is a fundamentally different experience from a tutoring center or an app. Most of our clients stay with us for multiple semesters.
Email Ryan@ShiresTutoring.com and mention which tutor and college town you're interested in, or fill out our Request a Tutor form. We typically respond within one business day.
That depends on where your student is starting and how consistently they show up. Dylan will identify the specific gaps, focus sessions on them, and adjust as the student progresses. Families who stick to a weekly schedule typically see meaningful progress within four to six weeks.
Email Ryan@ShiresTutoring.com and mention you'd like to work with Dylan at Middlebury College, or fill out our Request a Tutor form — you can also click the Request a Tutor button at the bottom of this page. We'll follow up within one business day to confirm availability and schedule your first session.