In 2003, when Natalie Woolsey was crowned as the Festival of Lights Pageant Queen, she found inspiration to initiate a toy drive for her community. This drive involved collecting toys throughout the town and encouraging future pageant contestants to contribute toys as part of their entry. Tragically, Natalie's life was cut short in a car accident in 2004, just one day before pageant rehearsals. However, at the time of her passing, her car was filled with toys, igniting a wave of inspiration among Texan communities to organize toy drives in her memory.

The Festival of Lights pageant contestants continued to place donation boxes around town, collecting toys in honor of Natalie, until the pageant concluded in 2011. During that year, a group of Natalie's close friends banded together and orchestrated a fundraiser to carry on her legacy. This endeavor marked the inception of the official Natalie Woolsey Toy Drive, which commenced with a successful bake sale generating $20,000.

Since that initial bake sale in 2011, the Natalie Woolsey Toy Drive has garnered immense support from volunteers and the community, amassing over $1 million in funds. It has evolved beyond being solely a toy drive, expanding its reach to encompass more meaningful endeavors. The Natalie Woolsey Toy Drive now hosts free book fairs, collaborates with school counselors to identify underprivileged children in the community, and not only provides toys but also essential necessities to deserving youngsters during the Christmas season.