Let the following sentence serve as a warning; if you missed Winterland and are susceptible to FOMO, please don’t read any further.

Winterland 2020 took place on Feb. 7, 8, and 9 in Historic Five Points. The third iteration of the DIY music festival founded by local musicians, producers, and impresarios Glenn Van Dyke and Lena Simon was, arguably, the musical happening of the year in Northeast Florida. With a dozen or so out-of-town bands from as far away as Portland (Sávila) and Leeds (Harkin), noise rock icons A Place to Bury Strangers and Florida faves Surfer Blood, as well as more than three dozen local artists, the three-day festival should be enough to keep even the most skeptical naysayers (you know, those who like to say “there’s nothing going on in Jacksonville”?) quiet for a spell.

While the music was the main event, the streets of Five Points were also quite the spectacle. As evidenced by these beautiful street style  snaps by Toni Smailagic, Northeast Floridians turned out in their Sunday best for Friday’s, Saturday’s, and Sunday’s festivities. Check out the gallery below to see nearly everything we love about Winterland and Toni Smailagic.

It may have been winter, but the vendor market was blessed with pretty damn near perfect weather all weekend.

Local creative Tenny Rudolph with some pre-gig love for The Black Toilet, who performed on Saturday.

Sound-people of sound mind and sound bodies, Lena Simon and James Rubia. Rubia did double duty, running sound at Hoptinger and performing as Animal Clinic, while festival-runner Simon’s contributions were unable to be counted on one or two hands.


A beautiful day in the (city’s coolest) neighborhood.

Tenny Rudolph, always stylin’, always smilin’


Che Forreign feeling it during her Saturday performance at Hoptinger.

Lots of style on the streets of Five Points for Winterland.

Animal Clinic can’t diagnose what ails your pup, but he can certainly soothe your broken heart with his vocal range, imaginative samples, and creative wordplay.


Festival founder Van Dyke, taking a breather whilst taking in Toni Smailagic’s book of imagery.

Squad goals with members of LOVE Culture and The Black Toilet.

Cherry Springer drummer Tyler Fleming strikes a pose before the boys’ set.

Van Dyke basking in the success of Winterland 2020

Miami’s Ben Katzman and his DeGreasers flexing before their show at Rain Dogs.

Don’t mess with door-person and Winterland All-Star volunteer Tiana… trust us… just don’t!

Be sure to check out Toni Smailagic’s first book of images, HERE.