What started as a small, grassroots effort in a local bar has now become one of East Dallas’ most important annual events. Founded a decade ago by Woodrow Wilson alumni Brian Bessner (Class of ‘93) and Clay Drury (Class of ‘92), WoodrowFest began as a modest fundraiser to help provide scholarships to students of their alma mater. The first event, held at The Pour House, featured a band, food, a few silent auction items, and raised around $3,500.

Fast forward 10 years, and WoodrowFest has grown into a two-day extravaganza, combining a golf tournament and family festival that raises approximately $30,000 annually. The money goes directly to support scholarships for Woodrow Wilson High School students pursuing higher education after graduation. Today, the Exchange Club of East Dallas proudly organizes the event, and they’ve expanded the scholarships to multiple $5,000 awards, including the prestigious $7,500 Brad Bradley Scholarship. These are renewable scholarships, meaning students can receive $20,000 to $30,000 over four years if they maintain a 2.5 GPA and a full course load. These scholarships have changed the lives of many deserving students, ensuring they can pursue higher education without the financial stress that often accompanies it.

This year, WoodrowFest will celebrate its 10th anniversary with even bigger and better events. On October 24th, the annual Golf Tournament at Tennison Golf Course will kick things off with a shotgun start at 11:30 AM. Golfers will receive range balls, carts, food, drink tickets, and a swag bag, along with a chance to win fantastic door prizes. Afterward, participants can head to White Rock Alehouse & Brewery for the tournament awards and a live broadcast of KTCK-FM The Ticket’s The Hardline.

On October 26th, the fun continue with a family-friendly festival at the Shakespeare in the Park Amphitheater, located at Samuell-Grand Park. Families can enjoy live music, food, and the ever-popular KidZone with bounce houses, face painting, and balloon animals, just to name a few. One of Woodrow Wilson’s student bands will perform, and the evening will be capped off with headliners like Prophets and Outlaws.

From its humble beginnings to what is now a key source of funding for Woodrow Wilson scholarships, WoodrowFest has become an East Dallas institution. Don’t miss out on this year’s milestone celebration—come out, have fun, and support the future of our community’s students!