Re-Enrollment

We’re grateful for the trust you’ve placed in Headwaters and the care you bring to your child’s education. Re-enrollment is an opportunity to reflect on the year behind us then look ahead together. This page outlines what to expect for the 2026–2027 school year, and how to move forward.

What’s Staying the Same 

At its core, Headwaters remains an intentionally small, relationship-centered learning community. Our commitment to experiential learning, time outdoors, mixed-age collaboration, and strong family partnership continues to guide our work.

On the instructional side, Mr. Kazmo will continue leading K–4, and Mrs. Laura will continue leading grades 5–8, allowing us to deepen our curriculum pilot with another full year of implementation with these grade bands. Both teachers will have increased support, enabling more responsiveness and depth in teaching and learning.

What’s Evolving for 2026–2027

We continue to move forward with Strom Farm and anticipate entering a lease this winter. The Strom family is working closely with Kane County to ensure shared clarity around the intended educational use of the land, even though a zoning permit is not required.

As we adapt our program to learning on and around the farm, we anticipate serving approximately 20–25 students in the 2026–2027 school year. The land at Strom Farm will offer expansive opportunities for outdoor, place-based learning, which will naturally enhance learning experiences, and we are actively assessing how the beloved features of off-site days will function for the school in a way that is sustainable for students, parents, and staff. Overall, we expect a more consolidated and consistent location schedule next year. Thank you again for your flexibility and patience this year.

To support our growth, we anticipate adding a full-time teaching assistant who can work across all age groups, bringing our on-site staffing to four adults. 

For next school year, we are considering high school enrollment on a case-by-case basis determined by staffing and space capacity. We anticipate offering a more defined high school program beginning in 2027.

School Leadership

Next year Headwaters will be led by either Kendra or by a newly hired Head of School, depending on timing and fit. Our long-term vision includes bringing on a Montessori-informed and/or nature-based school leader who can steward Headwaters into its next phase of growth when the structure, resources, and alignment are right. We are thoughtful and unhurried about this process, prioritizing cultural integrity, relational leadership, and deep alignment with our values.

Regardless of the outcome, Kendra will continue in a leadership role at Headwaters for the foreseeable future, ensuring continuity and ongoing stewardship of the school’s vision, culture, and operational systems.

Dana is transitioning to Board President, shepherding the nonprofit organization into its next phase of growth. She will also continue her hands-on academy work in programming and engagement, where she supports teachers, partnerships, student experience, and the relational life of the community.

Families can expect steady leadership, clear communication, and a values-aligned transition that keeps students, staff, and families at the center of every decision.

Tuition and Financial Overview

Tuition | Returning Families

Tuition for returning families for the 2026–2027 school year is $9,800 per student.

We are intentionally holding tuition steady for returning families in recognition of the flexibility, trust, and extra effort you’ve brought this year. We are so grateful you adapted alongside us as we moved to our temporary location at Wesley. We recognize the commute is a strain! Please accept this founding family rate for next year as a small token of our gratitude. 

Enrollment Deposit

A $500 enrollment deposit is required to re-enroll. The enrollment deposit confirms a year-long enrollment commitment and is applied toward tuition. It covers the first and last weeks of the school year (the final week of August and the first week of June). Regarding the school calendar: it’s similar to this year, with school beginning one week earlier to meet compliance as we seek ISBE recognition. The full academic calendar is available below.

The enrollment deposit is due by April 1. If you need additional time, extensions are possible, just reach out to us.

Payment Options

Families may choose one of the following payment options:

Pay in Full

  • Paid by June 30: 10% discount

  • Paid by August 23: 3% discount

Installment Plan

  • Tuition paid in 9 monthly installments

As part of our effort to simplify billing, the standard installment plan will move to a 9-month schedule. Families who prefer a 10-month payment plan may request one.

Fit and Continuity

Re-enrollment reflects a continued alignment between your family and Headwaters Academy. Our program is intentionally small, relational, and designed for students who thrive in experiential, community-based learning environments.

We remain committed to serving families who feel aligned with this approach and who value the close partnership between school and home that makes our community work.

Re-Enrollment Steps 

How to Re-Enroll

  1. Review the information on this page

  2. Submit the re-enrollment form

  3. Submit the enrollment deposit by April 1

Once these steps are complete, your child’s place for the 2026–2027 school year is secured.


Timing and Communication 

Over the coming months, we’ll share additional information about classroom preparation, community rhythms, and the start of the school year. Until then, no additional action is needed beyond completing re-enrollment steps.

Questions & Contact

If you have questions as you reflect on re-enrollment, you’re welcome to reach out to academy@headwatersil.org.

2026-2027 School Year Calendar 

School Day: 9:00-3:15pm

August 

First Day of School (Half Day 9:00-12:00pm) - Monday, August 24

Half Days (9:00-12:00pm)- Tuesday, August 25- Friday, August 28 

Teacher Workdays Afternoons (12:00-3:00pm) - Tuesday, August 25-Friday, August 28

First Full Day of School (9:00-3:15pm) - Monday, August 31

September 

Labor Day Holiday (No School)  - Monday, September 7 

Teacher Workday (No School) - Monday, September 21 

October  

Indigenous Peoples’ Day (No School) - Monday, October 12

Parent/Teacher Conferences (No School) - Friday, October 23

November 

Teacher Workday (No School) - Monday, November 2

Thanksgiving Holiday Break (No School) - Monday, November 23-Friday, November 27

December 

Winter Break (No School) - Monday, December 21-Friday, January 1 

January

Dr Martin Luther King Jr Day (No School) - Monday, January 18

Teacher Workday (No School) - Tuesday, January 19

February 

Presidents Day (No School) - Monday, February 15

School Improvement Day (No School) - Friday, February 26 

March

Spring Break (No School) - Monday, March 29 - Friday, April 2

April 

Parent/Teacher Conferences (No School) - Friday, April 9

School Improvement Day (No School) - Monday, April 26 (Flex day/emergency day)

May

Teacher Work Day (No School) - Friday, May 28 (Flex day/emergency day)

Memorial Day (No School) - Monday, May 31

June

Last day of school Half Day (9:00-12:00) - Friday, June 4