2023 Winona High School alumnus Bailey Holly (pictured second from right) is currently interning with the Mississippi Secretary of State's office in the Charities Division. The internship will provide valuable exposure to key sectors including charitable organizations, securities regulation, public land management, and business services.
Bailey is a Public Policy Leadership major with a minor in Disaster Sciences at the University of Mississippi.. She is part of the Trent Lott Leadership Institute, a member of the Sally McDonnell Barksdale Honors College, and is a member of Pi Beta Phi sorority.
She is the daughter of Trent and Amanda Holly of Winona.
Bailey is a Public Policy Leadership major with a minor in Disaster Sciences at the University of Mississippi.. She is part of the Trent Lott Leadership Institute, a member of the Sally McDonnell Barksdale Honors College, and is a member of Pi Beta Phi sorority.
She is the daughter of Trent and Amanda Holly of Winona.
ATTENTION: Affidavits for residency will be handled during registration at the WCTC.
With gratitude
Attention!!!!
There will be NO INTERNET or TELEPHONE service DISTRICT WIDE on Thursday, June 26.
The 2025-2026 District Calendar
Welcome to our new Tiger Perks Partner, Modern Woodmen of America. WMSD employees can enjoy FREE financial consultations on financial planning, retirement strategies, investments, Mississippi PERS and estate planning. Modern Woodmen members enjoy discounts at local restaurants, access to college scholarships, Do Good Grants, and other member benefits. Thank you, Matt Bennett and Modern Woodmen for your support of the Winona-Montgomery School District!
This incredible opportunity is available to ALL students of the Winona-Montgomery School District. The summer youth theater is in honor and memory of Patti Finley and Vanessa Miller, both of whom worked for the WMSD.
Happy Father's Day, Tiger Nation!
2025-2026 New School Year Registration!
Attention, parents!
Attention parents!
Attention, Parents!
Attention, parents!!!
Congratulations to all of our ALL A's ALL 9 weeks students at WSS! Your hard work and dedication has paid off!
Congratulations to the Class of 2025 Valedictorian and Salutatorian! The graduation ceremony will be held on Friday, May 23, 2025 at 7:00 P.M. at Tiger Stadium.
Public Notice
Principal's Statement
Good luck to Troylando Eden and Zaishun Nash as they compete in the NEMFCA All-Star game today!
Winona Secondary School Principal Terry Peeples graduated with his Doctor of Education in Educational Leadership K-12 from The University of Mississippi last week. His dissertation was Educating Students Suffering From Social Emotional Trauma. Congratulations, Dr. Peeples! We are so proud of all of your accomplishments.
