Craig and his wife Deb moved to the Hayward area in June of 2001. Craig spent the first six years of his administrative career as the Hayward Middle School Assistant Principal. Craig then moved into to the Principal role at the middle school where he spent four years. He was then asked to move into the Superintendent role where he has spent the last 14 years. Before moving to Hayward, Craig was a teacher and football, wrestling, and baseball coach at Freedom, Merrill, and Mosinee. Throughout his career, Craig has had the privilege to serve on numerous elected boards. Currently Craig is serving on the Wisconsin Association of School District Administrators Board of Control and also the WIAA Advisory Committee. Craig also is currently serving on the WIAA Conference Realignment Committee. Craig is both excited and humbled to be part of the Winter School District and is looking forward to serving this great community. His official start date is July 1 st and he can’t wait to meet everyone in the community and get to WORK! on assuring every student has the best opportunity to accomplish their individual goals.
12 months ago, Administration
Winter School District
Reminder about the upcoming Middle School/High School Band Concert. This includes 5th grade.
12 months ago, Administration
Winter School District
Youth apprenticeships allow students to gain real-world experience in their chosen field. This practical approach provides them with the skills and knowledge needed to perform tasks effectively in a professional environment. We are proud to be having this experience for our students! Thank you Ashley and Madison for bringing your work into our school!
12 months ago, Administration
Winter School District
Please give a warm welcome to our new Superintendent, Craig Olson. Welcome to the Winter School District!
12 months ago, Administration
Winter School District
Winter School District
Last night at Birchwood both JV and Varsity had strong performances. The varsity had their best team score of the year, aided by Dakota's 4 conference points, Jared's 10 and Adam's 24. This puts both Adam and Jared on the first team-all conference points list. On the JV side Noah Shannon tied his best round of the year, on his 16th birthday - nice job!!
12 months ago, Administration
Winter School District
Winter School District
Reminder to get those Summer School forms in
12 months ago, Administration
Winter School District
Reminder about Evacuation Drill tomorrow
12 months ago, Administration
Winter School District
Winter School District
The varsity team played the Cumberland invitational yesterday, competing against 12 other tough teams. It was one of our better teams performances. Justin Kinsley made his first varsity appearance, and played really well - consistent on both 9's. Dakota had his best front 9 of the year, but struggled on the back. Jared played very strong on both, and Adam placed 10th overall out of 65 golfers. Great job Warriors!
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
On May 13, we will be having a Triple P Workshop on Healthy Screen time routines. This will be held in-person and virtually. Dinner and childcare will be provided. Register here https://forms.gle/YA7xpxxmEjbqGBWn8
12 months ago, Administration
Winter School District
Winter 4th and 5th Grades were lucky enough to once again be invited to Hidden Acres Dairy for a farm tour. The day was packed with learning all of the ins and outs of a dairy farm. The teachers and kids are very thankful and grateful to have been invited and to have the opportunity to experience life on the farm! We were even spoiled with ice cream, ice cold milk, string cheese, and a goodie bag! Part 2
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
Winter 4th and 5th Grades were lucky enough to once again be invited to Hidden Acres Dairy for a farm tour. The day was packed with learning all of the ins and outs of a dairy farm. The teachers and kids are very thankful and grateful to have been invited and to have the opportunity to experience life on the farm! We were even spoiled with ice cream, ice cold milk, string cheese, and a goodie bag!
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Main Street looks amazing with our Senior Banners up!! Part 2
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Main Street looks amazing with our Senior Banners up!!
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Today, Mrs. Corbett had two classes at a time, Life Skills and Elementary Guidance, so the High Schoolers read to the Kinders and we had so much fun! Before the Kinders arrived, we picked out books and practiced mini lessons we could teach with the stories so each group could read a book and teach a mini lesson. When they were done reading, the Kinders taught the high schoolers what they were learning about Mindfulness in guidance class. It was a great time for the high school to practice being role models and for the kinders to practice re-teaching skills they are learning. We had a lot of fun. One of the many great things about being a small school and all in one building is that we can have all different ages interact and learn from each other.
12 months ago, Administration
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Winter School District
Last Parent Teacher Conference night, a visitor from out of town came to bring our school a bunch of cute little hearts to pass around and pass along for something called The Little Heart Project. It is a really neat thing - you can read more about it here : https://www.thelittleheartproject.org/ Today the 5th grade got to receive some little hearts with a little Guidance lesson on empathy and being mindful of our choices with what we think, do, and say. How a little kindness can have a huge impact.
12 months ago, Administration
Winter School District
Please see the letter below regarding the Evacuation Drill scheduled for Friday, May 2, 2025. This is only a drill.
12 months ago, Administration
Winter School District
Winter School District
Please note, that the Community Interview Committee meeting scheduled for Tuesday, April 29, 2025 has been canceled and will not be rescheduled.
12 months ago, Administration
The JV team had a very good night Thursday at Holcombe; 7 out of 8 players showed significant improvement over their last meet, with most having their lowest scores of the year. The team was led by good play from Justin Kinsley and Aden Arndt; Aden was 3rd overall at the meet and Justin taking 2nd. Great Job Warrior golfers!
12 months ago, Administration
Winter School District
Winter School District
We have lots of exciting things happening in the next couple of months! On Friday, May 2nd, our Parent Advisory Committee will be giving away FREE books! Stop in anytime between 8-12 p.m. If you didn't make it to the Car Safety Event, you can also grab the books and tote bag to start your car library!
12 months ago, Administration
Winter School District
Winter student, Kaylee Langham won Second Place in the Lions District 27 E1 Peace Poster competition and received a $75 check. Winter Area Lions Club President, Shaun Melarvie presented the check. Way to go Kaylee!!
12 months ago, Administration
Winter School District