Winding Roads is a 1999 American independent drama film produced and directed by Theodore Melfi in his feature directorial debut. Melfi wrote the screenplay with his future wife, actress Kimberly Quinn, who stars in the film with Katrina Holden Bronson and Rachel Hunter. James Marsters, Adam Scott, Michael Weatherly and Carlos Gómez co-star. The story centers on three women, all best friends, navigating their respective love lives.

Winding Roads was filmed in late 1998 in Springfield, Missouri, and produced through Melfi and Quinn's company Goldenlight Films. It was screened at the 1999 Austin Film Festival, premiered in Springfield on September 14, 2000, and was later shown in theaters in the Midwest.