The 5th Annual Legalized NYC Festival will take over Times Square’s historic Sony Hall on Monday, November 9, 2026, offering a fusion of conscious live music, industry insights, and cultural celebration.

This year’s event marks five years of recreational cannabis legalization in New York state. It also serves as the official kickoff destination for the prestigious High Times 2026 NY Cup, giving attendees exclusive access to register as official product judges or competitors.

Headlining the musical lineup is pioneering Jamaican deejay and reggae icon Big Youth, alongside celebrated roots reggae artist Ras Shiloh. Both artists will be backed by the veteran rhythms of Skadanks. Adding to the evening’s historic weight, The High Times CCB All-Stars will perform a special tribute to Peter Tosh, honoring the 50th anniversary of his seminal anthem, “Legalize It.” Rounding out the audio landscape are Hot 97 legends DJ Bobby Konders & Massive B Sound, bringing New York’s premier reggae-hip-hop sound system to the Sony Hall stage.

Beyond the music, the gathering functions as a premier fall harvest festival for the local cannabis community. The evening will feature curated panels with industry guest speakers, brand partnerships, sponsored giveaways, and a live broadcast.