BUY WEEKEND PASS HERE!

Single Day Tickets will go live:
mid-May

Windy Pop Weekender 2026

Sat & Sun 9/26 & 9/27
(Doors 4pm // Show 5pm)
@ Subterranean Upstairs (17+)
2011 W North Ave, Chicago, IL 60647 (Directions)

Performers

The Softies

Location:  Portland, OR / Vancouver, BC

Music  ✨  Website  ✨  Instagram

The Softies, comprised of Rose Melberg and Jen Sbragia, embody timeless themes of friendship and self-discovery through their minimalist pop soundworld.

more

Since their formation in 1994, they’ve created uncluttered and fearlessly vulnerable music, contrasting with prevailing trends. The Bed I Made, The Softies’ first new studio album in 24 years, showcases growth while reflecting on life’s complexities with lyrics drawn from real experiences. Despite individual pursuits and personal losses, Melberg and Sbragia reunite, channeling grief and rejuvenation into an album that captures the essence of their enduring friendship and offers hope and renewal amid life’s challenges. Through their perfectly-paired harmonies and telepathic playing, they navigate the present, past, and future, offering a poignant continuation of their musical legacy, resonating like time spent with an old friend who knows you best.

Rocketship

Location:  Portland, OR

Music  ✨  Website  ✨  Instagram

“Some of the best records are those that transcend the usual parameters of music to create worlds of their own. When it’s clear that what you’re listening to isn’t just a collection of that year’s songs, but a deeply thought-out, even architected space where ideas clash, converse, interlock; these are the albums that end up lasting well beyond their era, changing with us, and revealing new surprises we’ve never heard before every time we return to them.

more

…One of the clearest examples of an album that crafts a strange and beautiful world not quite like any other is Rocketship’s 1996 full-length debut A Certain Smile, A Certain Sadness. Even upon arrival, this was an experience unto itself, and 30 years later, these eight songs of bittersweet bliss still feel new. Slumberland is delighted to release a 30th Anniversary edition of this instant classic, making it readily available on vinyl and CD once again after years of being out-of-print.

Rocketship came into focus in the early ‘90s, incubating through some early 7”s and demos into their fully-realized album. The continuum of sounds that made up A Certain Smile, A Certain Sadness were recorded at home by bandleader and vocalist/songwriter Dusty Reske with help from members of the early lineup. While they sometimes melt into one another, each of the eight songs goes somewhere a little different. The bright, jangling guitars, zooming tempo, and co-ed vocals of brilliant opener “I Love You Like the Way That I Used to Do” blurs mod energy into something dreamier, practically blueprinting the next decade of indie pop in the process. The atmospheric weather patterns of “Heather, Tell Me Why” drift between melancholic acoustic guitars and gusts of overwhelming noise. It’s baroque pop from another solar system, but it doesn’t feel jarring when the bass-forward slow down of “Let’s Go Away” follows, or bounding fits of fuzzy enthusiasm like “Carrie Cooksey” enter the picture. The songs cautiously orbit each other, all glued together by that interplanetary all-tube M2 Hammond organ, loud in the mix. This was an album of unrepentantly vulnerable melodies, unusual seventh chords, lingering ambient interludes, and soft sentiments in a time when unfriendly, self-conscious punk rock was the order of the day. Even in the considerably gentler environs of the U.S. indie pop scene of the time, these were bold moves.

Returning to A Certain Smile, A Certain Sadness with fresh ears, it becomes more obvious how quietly influential the album was. After several different waves of shoegaze revivalism, grunge distillation, and new bands perfecting the ‘90s slacker pop aesthetic yet again, elements of Rocketship’s intricate creative world have begun to surface in the sounds of subsequent generations. Indeed, most examples of musically intricate, thoughtfully constructed, and emotionally unafraid indie pop of the last several decades are directly descended from Rocketship. Listening to a work so inspired, it’s no surprise that it ended up being extremely inspiring.

While the 30th anniversary of A Certain Smile, A Certain Sadness is the ostensible impetus for this reissue, what’s really being celebrated here is the album’s timelessness. Now, as it was then, this music is mystifying and comforting in ways that shouldn’t co-exist, and the softly glowing private world Rocketship built when they made this album is still as fascinating a place to get lost in as ever.”

Dressy Bessy

Location:  Denver, CO

Music  ✨  Website  ✨  Instagram

Dressy Bessy are an indie rock band formed in Denver, Colorado in 1997 by songwriter, vocalist, guitarist, and producer Tammy Ealom. The band is associated with The Elephant 6 Recording Co (Neutral Milk Hotel, Olivia Tremor Control, The Apples in stereo).

more

They have toured the USA as well as Canada, Europe, and Japan since the late 1990’s. Their most recent releases are KINGSIZED (2016) and Fast Faster Disaster (2019). The band has shared the stage and in some cases the studio with Peter Buck (REM), Mike Mills (REM), Scott McCaughey (Young Fresh Fellows), Steve Wynn (The Dream Syndicate), The Apples in stereo, Filthy Friends, Death Cab For Cutie, The Decemberists, Bright Eyes, Potty Mouth, amongst many others. Dressy Bessy also has had song placements in many television and motion pictures, including But I’m a Cheerleader (2000), Grey’s Anatomy (2003-2012), Californication (2014), The Powerpuff Girls, and many others.

good flying birds

Location:  Indianapolis, IN

Music  ✨  Website  ✨  Instagram

good flying birds is a noisy pop guitar group from the midwest USA. their debut album “talulah’s tape” was originally released in january 2025 on st. louis DIY rotten apple.

more

instantly selling hundreds of tapes and buzzing across online blogs, the band was picked up by Carpark Records and Smoking Room Records, who co-released a revamped “talulah’s tape” in october 2025. the album was met with critical acclaim from rolling stone, pitchfork, paste, allmusic, etc. and the band has been touring heavily since. their sound is marked by the wide-eyed spark of innocent love and gentle boy-girl dual vocals, carried by ripping guitars and spastic drums. somewhere between the lofi rock and roll of guided by voices and abrasive jangle of early mbv, with intricate riffs and passages that have earned an occasional “midwest emo” tag. Susie Slaughter (vocals/tambo), Kellen Baker (vocals/guitar), Luke Corvette (bass), and Ari Bales (drums), make up the live group, a tour de force of whirling pop attack that leans looser and fuzzier than the recordings. whether it be in a dank basement or a well-lit stage, they are a must see group in 2026.

The Tammy Shine

Location:  Denver, CO

Music  ✨  Instagram

On February 20, 2026, Tammy Ealom, the snarling creative force behind Denver’s legendary Dressy Bessy, presents her debut solo album The Tammy Shine, Ok Shine Ok, via Happy Happy Birthday To Me Records (HHBTM). This release marks a pivotal moment: for the first time in her three-decade career, Ealom has taken complete command—writing, performing, producing, and engineering the record entirely on her own.

more

Ealom’s resilience was forged early. Born to young parents, her upbringing as a “”military brat”” landed her in Hawaii, where she learned to literally fight to survive the rough social climate of high school. This tenacity would later serve her well in the male-dominated music industry. Her sonic DNA is equally eclectic, rooted in her Mod father’s love for the British Invasion bands, her discovery of The McCoys, Michael Jackson, Prince, and later refined by her love of grunge in bands like Nirvana and Hole. Her future husband and musical partner, John Hill (The Apples in stereo), also introduced her to more hard rock and the punk economy of The Ramones and Buzzcocks.
Tammy’s songwriting career jumpstarted in 1995 with a gift of a guitar and a 4-track recorder; weeks later, she had ten original songs recorded. After twenty-five years of crafting Dressy Bessy’s signature “”clutter-punk,”” Ealom began to form a singular vision. Sparked by a liberating solo set at the 2017 Athens Popfest, Ok Shine Ok is the result of that freedom.
The album highlights Ealom’s evolution from frontwoman to technical architect. Stripping away the democratic process of a band, she displays her prowess as a studio engineer, blending bubblegum hooks with DIY grit without an outside producer or band to interpret her vision.
To support the release, The Tammy Shine will begin touring in February 2026 with bassist Mike King. Ok Shine Ok is a celebration, proving that after thirty years of making noise, Ealom might just be getting started.
(Recommended if you like: The Beths, Alvvays, The Breeders, Veruca Salt, The Pretenders)

Calico Loco

Location:  Chicago, IL

Music  ✨  Instagram

Calico Loco will melt your face off, and then put it back on so you cry.

The Specific Heats

Location:  Boston, MA / Alburquerque & Santa Fe, NM

Music  ✨  Website  ✨  Instagram

The Specific Heats create garagey jangle pop infused with surf twang and a little dose of chaos.

more

Originating in Boston before relocating to Brooklyn, then New Mexico after a decade-plus-long hiatus, The ‘Heats returned in 2023 releasing a new ep “Decaydes Later” in 2024. Work then immediately began on their new LP “Everything We Never Were (but always wanted to be)” which the group will be self-releasing this year on their own label, Summer Man Records.

sunshy

Location:  Chicago, IL / New York, NY


Music  ✨  Instagram

sunshy is the punchy, dynamic Chicago noise-pop project of guitarist-vocalist Haoshu Sascha Deng, guitarist-vocalist Wesley Park, drummer Eric Breden, bassist Gwen Giedeman, and synth/multi-instrumentalist Jordan Zamansky.

more

They released their home-recorded, self-produced debut album, I don’t care what comes next, with Longinus Recordings in 2024, and was named “one of the most compelling bands of the ongoing Shoegaze resurgence” by Leor Galil of the Chicago Reader.

The Laughing Chimes

Location:  Athens, OH

Music  ✨  Instagram

Formed by brothers Evan and Quinn Seurkamp, Ohio band The Laughing Chimes calls on decades of jangly post-punk music while adding fresh melodic twists.

more

Their catalog is comprised of echoes from the best of the Flying Nun roster, mixed with the swirls of 90s Creation Records and midwestern lo-fi acts. The band released their sophomore album, Whispers in the Speech Machine, on Slumberland Records, which brought a southern gothic subversion to their previous work.

Cinema Hearts

Location:  Washington, DC

Music  ✨  Website  ✨  Instagram

An ex-pageant queen fronts a rock band? Cinema Hearts has a pulsing passion for days gone by.

more

It’s the sparkling indie rock project of Washington, D.C. singer-songwriter and former Miss America contender Caroline Weinroth, whose music captivates audiences around the world with playful lyricism, moody guitar riffs, retro song references, and dramatic pageantry. Backed by a powerful rhythm section, with Massimo Zaru-Roque on bass and Danny Ortiz on drums, Cinema Hearts presents a firecracker of a show. Following their 2024 SXSW tour, Rolling Stone picked Cinema Hearts as one of the best live acts to see.

time thief

Location:    Providence, RI

Music  ✨  Website  ✨  Instagram

time thief was formed in 2024 by James Walsh (DUMP HIM) and Zoë Wyner (halfsour, zowy). Their eponymous EP, released in September 2025, shows the two approaching songwriting in a more symbiotic way than on their last collab (DUMP HIM’s 2016 “venus in gemini”).

more

James + Zoë switch off on vocal and instrument duties throughout, with each song inspired by different records from the pair’s vast collection (including Eddy Current Supression Ring, Dolly Mixture, Boomgates, Henry’s Dress, and the Field Mice); the result is a record that doesn’t sound like it’s quite trying to be anything other than what it is. In true DIY spirit, the tracks were recorded and mixed by James (with help from Zoë), and Zoë handled the art.

The live band now includes Tyler Bisson (Audio Geography, Sun Urchins, tragwag) on drums, with Zoë and James trading off on bass and guitar duties.”

Blue Clovers

Location:  Champaign, IL

Music  ✨

Blue Clovers are a new indie-pop band featuring Kamila Glowacki and Joe Tucci.

more

Coming out of the central Illinois DIY music scene (Nectar/Macroplastics) their sound blends catchy vocal harmonies, heartfelt lyrics, and upbeat, jangly guitar and bass.