Orlando/ Fun & Entertainment

Orlando's Free Frontyard Holiday Festival Returns With The Frontmen, Maggie Rose

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Published on November 07, 2026
Orlando's Free Frontyard Holiday Festival Returns With The Frontmen, Maggie RoseDr. Phillips Center — Host Venue For Frontyard Festival
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Downtown Orlando is getting its holiday soundtrack back. The Frontyard Holiday Festival returns to the Dr. Phillips Center for the Performing Arts starting Nov. 27 and running through Dec. 31, bringing free concerts on scheduled event nights, themed party nights and fake snowfall to the Frontyard and Seneff Arts Plaza, with no events on Dec. 14, 15, 24 or 25.

The completely free outdoor event kicks off on opening night with the Swingin' Holiday Big Band, according to WDBO. The event is staged at the Dr. Phillips Center for the Performing Arts, which lists the Frontyard and Seneff Arts Plaza as the festival's home base for the season.

Country Supergroup Headlines Theme Night

The marquee date for country fans lands on Dec. 10, when Country Night brings The Frontmen to the stage. The trio is made up of Richie McDonald, formerly of Lonestar, Larry Stewart of Restless Heart, and Tim Rushlow, formerly of Little Texas, per the station's report. They're expected to run through genre staples including “Amazed,” “God Blessed Texas” and “The Bluest Eyes in Texas.”

The following night, Dec. 11, belongs to Maggie Rose, described in the same account as a two-time Grammy-nominated singer-songwriter bringing her Nashville sound to Orlando. Her nominations came for the album No One Gets Out Alive and the single Poison in My Well, and she's also released the record Half Moon. A night later, on Dec. 12, Broadway and concert headliner Michael Cavanaugh presents A Merry Rockin' Christmas, a show the article notes blends seasonal favorites with covers of Billy Joel and Elton John.

Jazz, Latin and Yacht Rock Nights Round Out the Calendar

Jazz gets its own spotlight on Dec. 19, when vocalist and violinist Emmaline performs Have Yourself a Jazzy Little Christmas, the same account reports. Additional acts scattered throughout the month include BK Jackson's Jingle Jazz Tour, CeCe Teneal and Gary Lovini, though exact dates for those performances were not specified.

Beyond the national names, the festival is also leaning on Central Florida's arts institutions. Opera Orlando, the Orlando Gay Chorus, the Bach Festival Choir, the Brass Band of Central Florida and various area high school choirs are all scheduled to perform, according to the station's report. The lineup mixes national headliners, Broadway stars and jazz performers with those local arts organizations for a season-long rotation of seasonal music and community showcases.

Themed nights extend beyond the headliners, too. The Community Paper reports that the festival, now in its second year, also includes Latin Night on Dec. 3 and a Yacht Rock Night on Dec. 17 featuring New Kids On The Yacht, building toward a New Year's Eve party on Dec. 31 that closes out the run.

Snowfall, Firepits and Free Admission

Dr. Phillips Center's own announcement describes a broader slate of attractions planned alongside the music, including live entertainment, firepits, holiday movie screenings, seasonal beverages and treats, nightly snowfall, interactive experiences and light displays. The Community Paper separately reports nightly extras such as fake snowfall, holiday crafts, games, snacks, hot cocoa and cocktails for festivalgoers browsing the plaza between sets.

Admission to the festival remains free, though food, beverages and select activities will be available for purchase on-site, WDBO notes. Organizers point to the Dr. Phillips Center's Frontyard Festival website for the complete schedule and exact showtimes as the Nov. 27 opening approaches.