Jazz Saxophonist Flautist Smooth jazz artist. Shows at 4:30pm & 7:30pm

Béla Fleck & The Flecktones reunite to perform Jingle All the Way, their Grammy-winning holiday album blending jazz, bluegrass, and global sounds.

Dozens of Holiday Ice Art Sculptures on display throughout downtown! Shops open late and make sure you see the town's 20 ft real tree all lit up. The tree will be lit at 6pm. Free to attend, free to park. Always the Friday after Thanksgiving.

The Ukulele Orchestra of Great Britain sings and strums its way through a witty, virtuosic all-ukulele performance featuring clever takes on classic tunes.

An icon returns to the heart of the jazz world—and the Maryland Hall stage. With over 30 years of synergy and nearly no lineup changes, the Quartet commands the stage with original compositions and masterful interpretations of jazz and pop classics.

It’s become an annual tradition to welcome the region’s preeminent Grateful Dead tribute band to the Root Family Stage at Omi’s Pavilion.

Big Kid Dance is a queer dance movement community based in Philadelphia. They create collaborative, thought-provoking contemporary dance works reflecting on love, grief, and identity.

Navy Football hosts VMI as they kick off the 2025 season in Annapolis! Get your tickets today and join us for all the excitement of the first football game of the season!

Come join us at 3:30 p.m. as we take on UAB! This game will be sponsored by HII.