Osees, Blonde Redhead, Caroline Rose and More | Here’s what to expect from Winterland Six in Jacksonville

Winterland, the annual indie- and local-music-focussed Jacksonville-based music festival is returning for its sixth year in February – this time to James Weldon Johnson Park in the middle of Downtown Jacksonville. Headliners for this year’s three-day festival include the legendary Brooklyn experimental trio Blonde Redhead, inimitable singer-songwriter Caroline Rose and San Francisco psych-rock lords Osees (formerly known as Thee Oh Sees, The Ohsees and Oh Sees).

The three headliners are joined on the three-day bill by nationally touring acts including Chicago sax master Isaiah Collier, Louisville indie trio Wombo, Nashville Southern rockers Thelma and the Sleaze, New York jazz-guitar great Ava Mendoza, FL-by-way-of-LA singer-songwriter Laney Tripp and more, plus lots of locals, including Ebony Payne-English, Rambler Kane, Huan, Ebonique, Seagate, Erica Reese, Yaupon Holly, K.UTIE, Bobby Kid and more. 

In addition to the more than two-dozen performances, Winterland Six will feature artist-education panels, DJ sets and family-friendly activations throughout James Weldon Johnson Park, with food trucks and beverage offerings throughout the weekend. 

Winterland Six at James Weldon Johnson Park kicks off Friday, February 23 at 4 p.m. and continues at 2 p.m. on both Saturday, February 24 and Sunday, February 25. Single- and three-day music passes are on sale now here.

Read more about some of the artists performing at this year’s Winterland and stream their latest music below. 

Experimental/Post Rock/Indie

Blonde Redhead

Recommended If You Like: Stereolab, Beach House, Radiohead

The Brooklyn-formed experimental group Blonde Redhead is one of those bands that, if you like them, they’re probably your favorite band. In September, the group returned with their first album of new music in nine years – a long time to wait for its army of diehards. The lead single, “Snowman” is a good example of the kind of enjoyably unconventional soundscape for which the band is known.

Stream

Singer-Songwriter/Pop 

Caroline Rose

Recommended If You Like: Sharon Van Etten, Chastity Belt, Alvvays

Over four full-length albums, the singer and multi-instrumentalist Caroline Rose has continued to expand their sound, exploring new territory while remaining one of the most critically-appreciated songwriter’s of their generation. Rose’s emotional, breakup-tracing fourth album, 2023’s The Art of Forgetting, is their most sonically ambitious record to date, and the tour for the album was arguably one of the most buzzed-about live-music events of 2023. (Watch KEXP’s Cheryl Waters gush about it and the new record during Rose’s live session above.)

Stream 

Psychedelic Rock 

Osees

Recommended If You Like: Ty Segall, King Gizzard & the Lizard Wizard, Frankie and the Witch Fingers

Led by the uncontainably frenetic frontman John Dwyer, for going on three decades Thee Oh Sees (or The Ohsees or The Oh Sees, or Oh Sees, or currently: Osees) have been on the forefront, and stayed ahead, of every successive garage-rock revival. The band’s latest, 2023’s Intercepted Message, is the group’s 26th studio album. With garage-pop ditties, electro-dance bangers and plenty of proto-punk pummel, it showcases the band at its best volume – 11 or higher. 

Jazz

Isaiah Collier

Recommended If You Like: John Coltrane, Alice Coltrane, Pharoah Sanders

One of the current standouts of Chicago’s red-hot jazz scene, 25-year-old saxophonist Isaiah Collier is reshaping spiritual jazz for a new generation. His latest, 2021’s Cosmic Transitions, was recorded on what would have been John Coltrane’s 94th birthday and was subsequently namechecked as the best jazz album of that year by several tuned-in publications. Collier and his band, the Chosen Few, also do a stunning, very-extraterrestrial version of “Lift Ev’ry Voice and Sing,” the Black national anthem, which notably was written here in Jacksonville by James Weldon Johnson. 

Stream  

Post Punk 

Cumgirl8

Recommended If You Like: Stuck, Cola, Tanukichan

New York City collective Cumgirl8 pairs their catchy post-punk wallop with madcap energy and a performance art bent, all of which has made them a much-buzzed about live act. The group’s latest, the 2023 EP Phantasea Pharm, is a six-song detonation of an intriguing mix of sludge, stoner rock, punk and pop that Pitchfork says spotlights the group’s “sleazy wit.” 

Stream

Rock/Blues/Southern Rock

Thelma and the Sleaze

Recommended If You Like: Du Blonde, Death Valley Girls, Shannon & the Clams

Nashville-based Southern-rock quartet Thelma and the Sleaze pack a heavy punch, deploying big rollicking riffs and earworm-y hooks as they carry the torch for the melding of blues, rock and country. 

Stream

Jazz

Ava Mendoza – “Diablada” 

Recommended If You Like: Mendoza Hoff Revels, King Khan, Madadkin

In the niche world of contemporary avant-garde jazz, guitarist Ava Mendoza is a household name. On her latest, Mendoza leads a trio of collaborators who are similarly lauded. On “Diablada” the first single from her album with supergroup Ava Hoff Revels, Mendoza and company – tenor saxophonist James Brandon Lewis, electric bassist Devin Hoff and drummer Ches Smith – take their music to unanticipated and rewarding heights. Read Daniel A. Brown’s full review. 

Stream 

Indie Folk

Laney Tripp – “Movin’ On”

Recommended If You Like: Barrie, Hovvdy, Angel Olsen 

Florida-bred singer-songwriter Laney Tripp’s latest five-song collection, Cedar Island Songs, sounds damn-near subaqueous. Cut with Burlington, VT superproducer Benny Yurco, and capped by “Movin’ On,” the new record floats on a vast, sparkling sea of experimental folk. Read the review here. 

Stream

Winterland Six takes place in James Weldon Johnson Park in Downtown Jacksonville and kicks off Friday, February 23 at 4 p.m. and continues at 2 p.m. on both Saturday, February 24 and Sunday, February 25. Single- and three-day music passes are on sale now here.