Throughout the year, Glenwood hosts a number of events to celebrate the season. During our fundraisers and friend-raisers, guests have the opportunity to meet our kids and network with a who’s who of the Chicagoland business community as well as local leaders and community members.

For more information about any event, please contact Jen Wolff, Director of Special Events & Corporate Sponsorship at


Associate Board Wine Tasting

The wine tasting is hosted annually by Glenwood Academy's Associate Board. The event showcases exquisite wines through guided tastings along with a paired buffet of appetizers. The Associate Board is also a vital part of how Glenwood supports our students and families. This group of young professionals helps to raise necessary funds and provides mentoring to our students through various activities and service projects on campus.

Steps For Students

Glenwood Academy’s 5K Walk is our signature family fun walk held in the fall. The walk brings together our entire community- students, their families, staff, our neighbors, and community members to raise funds to enable us to forever change the lives of our students and enhance the lives of their families and improve the fabric of their communities. 

Community Celebration

Community Celebration is an evening of food, festivities, and fun! This community event features the Glenwood Gourmet Fest, a silent auction, kid-friendly activities, and opportunities to spend time with Glenwood students. Click here for more information. 

Flag Day 

Flag Day is our annual event to celebrate students' accomplishments for the past school year. We welcome you to join faculty, staff, alumni, and parents to honor and celebrate our fantastic students!

Beginning with a chapel service, followed by a military drill competition, a battalion formation, awards ceremony, and a pass-in-review, see how our students have come together to form a complete unit.

Glenwood Academy's Golf Outing

The Glenwood Academy's Golf Outing begins with a luncheon and wraps up with an elegant post-round dinner and program featuring great raffle prizes and a live auction.

Thanksgiving Luncheon

Glenwood Academy's Annual Thanksgiving Luncheon gives donors, alumni, and friends the opportunity to share a meal and kick off the holiday season with the children of Glenwood. The luncheon also features a paddle raise and live auction.  

 Pledge Service

Glenwood Academy's annual Pledge Service and Holiday dinner is a way to celebrate our wonderful donors, students, faculty, alumni, and friends. This is a ticketed event.  

Open House

Glenwood Academy hosts Open Houses on campus throughout the year for prospective parents and students to visit the campus, tour the facility and learn more about what the Academy has to offer.  To RSVP or for more information, please contact us at (708) 754-0175.



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