— Explore Essential Insider Insights —

A successful Middlebury Application does not include College-Specific Supplemental Essays—so students should focus on crafting stand-out content throughout their Personal Statement, Comprehensive College Resume, and more!

Below, learn more about the Supplemental Essay Process for the majority of colleges that are selective—like Middlebury—and start your college admissions success story! Planning ahead can bring more colleges within your reach—including Middlebury!

— Repeats & Remixes —

While many colleges have applicants address the same Supplemental Essay Prompts year after year, some colleges change up their Specific Supplemental Essay Prompts. When a college decides to shake things up, they may change the number of supplemental essays assigned to applicants, modify an essay’s maximum word count, adjust specific wording within a prompt—or even overhaul the entire supplemental essay topic!

— The Most Recent Rule —

Current High School Class of 2027 Students can prepare most effectively by reviewing the most recent supplemental essay prompts. The Most Recent Supplemental Prompts for this college have been shared above! Each college’s most recent supplemental prompts are the prompts that were addressed by Class of 2027 High School Applicants. You can make informed prompt predictions by comparing these prompts with the past prompts addressed in our Accepted Alumni Inspiration!

— Trends Worth Following —

With our Accepted Alumni Inspiration, we share past supplemental prompts, so you can get an idea of a college’s Supplemental Prompt Trends. Be sure to draft any college-specific supplemental essay based on careful planning, informed projections—and with all of the Official Supplemental Essay Prompts following their release on August 1st. In advance of August 2026, be sure to utilize Insider Information shared in our Upgraded Guides. There, we share success-proven methods to help you plan, prepare, and create before the Supplemental Essay Prompt Release Date: August 1st, 2025!

— The Pre-August Process —

Official Supplemental Essay Prompts for Class of 2027 Applicants will be published August 1st, 2026. That’s why we help students build content they can redefine, repurpose, and reimagine for every possible supplemental prompt—through The Upgraded Supplemental Essay Guides. With our Supplemental Strategy, we help launch success for every student’s supplemental essay-building process, starting off with the most essential Insider Innovation: The Upgraded Supplemental Essay Styles.

— Supplemental Success Strategy —

We’ve engineered the ultimate head-start for students applying to selective colleges, those with lengthy college lists, those with busy schedules, and those who want to finish early! Our decade of successful essay coaching helps our current students design their own optimal Supplemental Strategy.

— The Seven Supplemental Styles —

Through innovative approaches including The Supplemental Essay Styles, our students are able to craft inspiring supplemental essays at a sustainable pace—and achieve more success during the admissions process. Discover our Supplemental Essay Strategy and all Seven Supplemental Essay Styles in the Innovation Section of this Supplemental Essay Guide!

— Upgraded Class of 2027 Essentials —