Annie

This holiday season, Gateway Theatre invites families and theatre-lovers to experience the heartwarming story of Annie, one of the world’s best-loved musicals, from December 11 to January 3, 2026. Directed by acclaimed Canadian theatre artist, Josh Epstein, this Tony Award-winning musical has captured hearts around the globe with its toe-tapping songs, exuberant dancing, and one very lovable dog.

Set in 1930s New York City, little orphan Annie charms everyone with her courage and positivity, despite living a “hard knock life” at Miss Hannigan’s cruel orphanage. When she is unexpectedly invited to spend the holidays with billionaire Oliver Warbucks, Annie embarks on a fun-filled adventure alongside the cutest stray dog named Sandy, and eventually finds her forever home and family. Played by a real, live dog, Sandy adds heart-melting charm to the stage, delighting audiences of all ages.

“There’s something truly magical about seeing little Annie’s optimism light up the stage, and when Sandy bounds in, well, it’s impossible not to root for them,” says Director Josh Epstein. “This production celebrates hope, joy and the power of connection. It’s everyone’s favourite classic musical that will tug at your heartstrings and have you hugging your loved ones a little tighter this holiday season.”

Winner of seven Tony Awards, including Best Musical, Annie features a beloved book by Thomas Meehan, music by Charles Strouse, and lyrics by Martin Charnin, and has become a worldwide phenomenon since its Broadway debut in 1977. With iconic songs like “Tomorrow”, “Maybe”, and “It’s The Hard Knock Life”, Annie offers a refreshing and joyous taking on a holiday classic. Equal parts spectacular dancing, family-friendly fun, and heartfelt storytelling, this production features a talented mix of youth and professional artists, alongside a loveable canine co-star, Sandy, whose presence on stage adds spontaneous smiles and an extra layer of festive warmth.

Tickets start at $43 and can be purchased online or by calling the Gateway Theatre box office. Performances are from Thursday, December 11, 2025 to Saturday, January 3, 2026. This show is recommended for ages 5 and up.

Throughout the run of Annie, audiences are invited to participate in a special in-person raffle. The grand prize is a luxurious trip to Victoria, including round-trip flights courtesy of Helijet, an overnight stay at the iconic Fairmont Empress, and a $250 gift card to select award-winning restaurants. It’s a chance for audiences to make their holiday experience with Annie even more memorable while supporting live theatre in Richmond.