Downtown Orlando is gearing up for a month-long holiday celebration as the Dr. Phillips Center for the Performing Arts brings back its annual Frontyard Holiday Festival later this month.

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Kicking off on Nov. 27 and running through Dec. 31, the completely free outdoor event transforms the venue’s Frontyard stage into a vibrant hub for seasonal music, community showcases, and family-friendly entertainment. This year’s lineup features a diverse mix of national headliners, Broadway stars, jazz performers, and top-tier local arts organizations.

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Headliners and Special Performances

Music fans can expect a packed calendar spanning country, jazz, holiday classics, and Broadway favorites:

Nov. 27: Opening night features the Swingin’ Holiday Big Band.
Dec. 10 (Country Night): The country supergroup The Frontmen take the stage. Composed of Richie McDonald (formerly of Lonestar), Larry Stewart (Restless Heart), and Tim Rushlow (formerly of Little Texas), the trio will perform signature hits like “Amazed,” “God Blessed Texas,” and “The Bluest Eyes in Texas.”
Dec. 11: Two-time Grammy-nominated singer-songwriter Maggie Rose brings her Nashville sound to Orlando, hot off nominations for her album No One Gets Out Alive and single “Poison in My Well,” alongside her latest release, Half Moon.
Dec. 12: Broadway and concert headliner Michael Cavanaugh presents A Merry Rockin’ Christmas, blending seasonal favorites with high-energy covers of icons like Billy Joel and Elton John.
Dec. 19: Jazz vocalist and violinist Emmaline performs Have Yourself a Jazzy Little Christmas.

Additional acts featured throughout the month include BK Jackson’s Jingle Jazz Tour, CeCe Teneal, and Gary Lovini.

Celebrating Central Florida Talent

True to its community focus, the festival will shine a spotlight on prominent local arts groups. Scheduled performers include Opera Orlando, the Orlando Gay Chorus, the Bach Festival Choir, the Brass Band of Central Florida, and various area high school choirs.

Themed Nights and Festival Details

In addition to the nightly music, visitors can enjoy several recurring themed experiences mid-week:

Dec. 3: Latin Night
Dec. 10: Country Night
Dec. 17: Yacht Rock Night

Admission to the festival is free, with food, beverages, and select activities available for purchase on-site.

For the complete schedule, exact showtimes, and up-to-date festival announcements, visitors can check the Dr. Phillips Center Frontyard Festival website.

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