Superintendent of Schools
Dr. Craig Winkelman started in his role as Barrington 220's Superintendent of Schools on May 1, 2023.
He is a familiar face in Barrington 220, bringing significant experience and leadership in education. Dr. Winkleman previously worked as the district’s Deputy Superintendent, as well as the district’s Assistant Superintendent for K-12 Schools & Operations. In his roles, he oversaw key district initiatives (Transform 220, Equity 220, Framework 220 and Safety 220), supervised and evaluated all principals, tracked policy updates for the Board of Education, led district leadership meetings, and worked closely with community organizations as a strategic partner.

Dr. Winkelman began his career in education in Barrington 220 in 1997, working as a Special Education Teacher at Barrington High School. He went on to work as the Assistant Principal at Station Campus, then as a Principal in Community Consolidated District 15 for two years. In 2006 he returned to Barrington 220 as the Principal of Station Campus, a position he held until 2017. He holds an associate’s degree from Harper College, a bachelor's degree in Special Education from Illinois State University, a master's degree in Educational Administration from Northern Illinois University, and a doctorate in Educational Leadership from National Louis University. In 2020 he received the Harper College Distinguished Alumni Award.
Dr. Winkelman resides in the Barrington area with his wife Amy, who works at BHS. Their two daughters attended Countryside Elementary, Station Campus, and BHS. Click here to learn more about Dr. Winkelman, as featured in Quintessential Barrington.

Contact
Dr. Craig Winkelman
Superintendent of Schools
cwinkelman@barrington220.org
Jeanine Stark
Executive Assistant
jstark@barrington220.org
847.842.3537

Authentically 220: Checking Out Learning in Our Schools!
Each year, Dr. Winkelman enjoys showing you the amazing things happening between all 13 of our buildings. This year's focus is on authentic learning. What exactly is that? As defined by the accompanying image, these are learning activities that are carried out in real-world contexts or have high transfer to a real-world setting that are personally/culturally relevant, student-centered, and actively engaging.
We are releasing a new episode in each month's 220 Connection district newsletter between now and May 2026! Check out each of our first four episodes below!
Most Recent Episode (March 2026):
Check out previous episodes!
- Episode 3: A Sugary Surprise & Racing The Superintendent at BMS-Prairie
- Episode 2: Launching Student Announcements at Roslyn Road
- Episode 1: Exploring Nature with the ELC & Squirmy Science at North Barrington
Episode 3: A Sugary Surprise & Racing The Superintendent at BMS-Prairie
Episode 2: Launching Student Announcements at Roslyn Road
Episode 1: Exploring Nature with the ELC & Squirmy Science at North Barrington
2025-2026 Theme: B Real
Barrington 220 has been known for having a dedicated theme for each school year, and in 2025-2026, it's to B Real!
With an emphasis on authentic learning, we seek to embrace real-world learning opportunities and connections for our students in what we teach and what they are able to learn. You can hear Dr. Winkelman talk more about it as part of the Opening Day highlight reel below:

All in 220:
During the 2023-2024 and 2025-2026 school years, Dr. Winkelman's video series, All in 220, recognized the students, staff members, and community members who always go above and beyond to support Barrington 220 schools. Click the logo below to watch!
