HHA Harry Hustle Fun Run Highlights: Confidence, Community, and Joy!
- Jami Wilhelm
- 17 hours ago
- 3 min read
At Hickory Hill Academy right here in Madison, Wisconsin, our community shines brightest when we come together, and the annual Harry Hustle fun run is the perfect example. It’s a day full of movement, laughter, and connection — celebrating the confidence and spirit of every student.

This year’s Harry Hustle was a huge success, uniting students from Kindergarten through 8th grade, along with our youngest learners in Pre-K and preschool, for a day filled with smiles, cheers, and celebration.

Building Confidence Through Movement
The Harry Hustle course is thoughtfully designed for every age group.
K–8 students took on longer routes that challenged their endurance and celebrated their growing independence.
Pre-K and preschool students enjoyed shorter, age-appropriate paths that helped them build confidence and experience the joy of crossing the finish line.
This inclusive approach allows every child to feel proud, capable, and part of something bigger — all while developing gross motor skills and a love for physical activity.

A Day of Fun, Encouragement, and Connection
The energy on campus was contagious as families, teachers, and friends lined the sidelines, cheering on every runner. The encouragement and applause gave students that extra boost to keep going and finish strong.

Even our infant and toddler classes joined the fun, cheering on their older friends and enjoying bubble time on the sidelines. Their laughter and excitement captured the true spirit of community that defines Hickory Hill Academy.

Lunch and Kindergarten Preview for Pre-K Families

After their big race, our Pre-K students and families gathered for a special complimentary lunch in the K–8 building. Prepared by Chef Chris, the meal highlighted the quality and care behind our school’s healthy lunch program. Families shared food, laughter, and conversation — making it a meaningful way to celebrate together after the run.

We’re also excited to invite families to our upcoming Kindergarten Preview Day on October 28, 2025, from 8:30 – 10:30 AM. It’s a wonderful opportunity to explore our Kindergarten classrooms, meet our teachers, and see firsthand how Hickory Hill Academy inspires curiosity, confidence, and academic growth from the very start.

Growing Strong Bodies and Confident Hearts
The Harry Hustle is more than just a race — it’s an opportunity for students to build strength, coordination, and confidence through play. Running, jumping, and cheering all help children develop essential motor skills while nurturing teamwork and a lifelong love of movement.

Powered by Community
Events like the Harry Hustle wouldn’t be possible without the help of our incredible teachers, volunteers and supportive families. From setting up the course to handing out water and snacks, your involvement reflects what makes Hickory Hill Academy so special — a private school community where everyone belongs and works together for our students’ success.
Looking Ahead
As we wrap up another wonderful year of the Harry Hustle at Hickory Hill Academy, we’re already looking forward to next year’s event. Each year brings new opportunities for growth, connection, and fun — and we can’t wait to see how our students continue to build confidence and community.
At Hickory Hill Academy, the Harry Hustle isn’t just an event — it’s a reflection of who we are: a private school in Madison, WI, where students grow in confidence, character, and compassion.
We’d love for you to help us spread the word! Invite your friends to join us at our upcoming Open House events. It’s a wonderful chance for families to see what makes HHA special and experience our vision of cultivating compassionate leaders in action.
Let’s keep that spirit alive all year long — moving, cheering, and growing together!