Winterland IV | Here’s what you need to know about Downtown Jax’s big FREE indie-music fest

What you'll see and hear at this weekend's Winterland IV

Press photo collage of winterland headliners
Headliners for Riverfront Plaza's Winterland IV music festival (from left) Caroline Rose, Reggie Watts, Hunx and his Punx and Slothrust | Credit: press photographs courtesy of Winterland

The two-day Winterland music festival kicks off in Downtown Jacksonville’s Riverfront Plaza (the former the site of the Landing) this weekend.

The fourth iteration of Winterland, a locally founded festival, will feature nearly two-dozen local acts performing alongside big-time Sunshine State natives like Glove and Las Nubes, as well as national headliners, including popular indie rock bands Hunx and his Punx and Slothrust, as well as alt-country singer-songwriter Caroline Rose and multi-hyphenate (musician, comedian, vocal artist, social media sensation) Reggie Watts.

It’s the kind of unique, grassroots music event that, thanks to Winterland, now comes around Jacksonville at least once a year. And, it’s FREE to attend.

Here’s what you need to know about Winterland IV.

What the heck is Winterland?

“We started Winterland as a way to help usher in a new era of music culture in Jacksonville.”

Winterland founder Glenn Van Dyke in a Folio Weekly article from February 2020.

Yes, this is the fourth iteration of Winterland. If this is your first time hearing about the festival, here’s a little background: The first Winterland took place inside the now-defunct Space Gallery in Downtown Jacksonville. Since then the founders –– local musicians/producers Glenn Michael Van Dyke and Lena Simon –– have been expanding the festival’s footprint. Winterland II was held across several venues in Five Points. In February of 2020, Winterland III returned to Five Points, adding a vendor market, interactive art installations, panel discussions and more to the fest, which had ballooned to include nearly 50 bands over two nights and three days.

This year’s Winterland features more than 30 artists performing on two stages. The vendor market is back, this year run by the folks behind the popular Vagabond Flea. Interactive installations created by local artists are on tap, as is beer, wine and liquor.

Where the heck is it?

Winterland IV is held at Riverfront Plaza. Located on the banks of the St. Johns River in Downtown Jacksonville, this big grassy field was, for decades, the site of the Landing.


Festival site Winterland IV
Site map of Winterland IV festival grounds

When the heck is it?

The music starts on Saturday, February 26 at 1:30pm with South Florida’s Cult of Ugliness and continues late into the evening. Saturday’s must-see performers include, but are not limited to, Jax jazz quartet Madre Vaca (5:00pm) Duval hip-hop collective L.O.V.E. Culture (7:15pm) and headliner Reggie Watts (9:00pm). On Sunday, Jax indie rock band Bobby Kid kicks things off at 12:30 pm, followed by local bedroom pop standout Sailor Goon (1:00 pm). Sunday’s highlights include goth-y Tampa industrialists Glove (5:30 pm), Jax’s mighty Afro-Cuban salsa orchestra LPT (8:00 pm) and –– all the way from San Francisco –– Hunx and his Punx, who close things out with their infectious bubble-gum thrash (9:00 pm).

How much do tickets cost?

Winterland IV is free to attend. That’s more than a fair price given the quantity and quality of music on offer. To help offset the costs, though, the festival runners are offering support packages, which include a festival tee, a seed paper poster and a up-cycled cup that’s good for discounts on beverages all weekend long.

“We have some sponsors this year, but we still need your support to make this happen. We are an artist-run collective spreading ourselves to maximum effort in order to bring YOU cool happenings. Everything we make from our festival and shows goes to paying artists, staff, and ensuring that we can continue to bring more wild imaginations to life. #supportyourlocalscene”

From the official website of Winterland IV

Will I like the music?

With more than 30 artists performing in a range of genres, from folk and Americana to bedroom pop, hip-hop, jazz, electronic, all flavors of rock (garage, psych, shoegaze, etc.) and more, there’s something for everyone at Winterland IV. For a taste test, check out our playlist below.

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