top of page

Cassadee Pope Live at The Loft: An Acoustic Night of Nostalgia, Humor, and Honesty

Cassadee Pope’s acoustic set at The Loft at City Winery in Philadelphia proved that a stripped-down show can sometimes hit the hardest. With just her guitar, her voice, and a room full of fans, she created a night that felt intimate, warm, and disarmingly honest.


Cassadee Pope playing guitar under blue and purple stage lights at a venue with "LOFT" sign. Audience seated, creating a cozy ambiance.
Cassadee Pope performing at City Winery in Philadelphia, PA - Photo by Rebecca McDevitt (IG: @rebeccajeanlimitedphotography)

She wasted no time diving into nostalgia, pulling out Hey Monday classics like “Homecoming” and “6 Months”. Hearing those songs in a small acoustic space gave them a new kind of softness, like she was revisiting her younger self with clarity instead of chaos.


But Cassadee didn’t stay in the past. She blended eras effortlessly, performing the title track “Hereditary” from her album Hereditary with a confidence that proves she’s come back to her pop-punk roots stronger than ever. She even sprinkled in what she affectionately called a “y’allternative” sound, reworking older material to match the pop-punk lane she’s carving herself back into. A highlight was “Coma”, her collab with Taylor Acorn, which hit especially hard.



Cassadee Pope sits on stage in front of a rustic wooden backdrop, playing guitar and singing into a microphone. Warm stage lighting creates an intimate mood.
Cassadee Pope performing at City Winery in Philadelphia, PA - Photo by Rebecca McDevitt (IG: @rebeccajeanlimitedphotography)

What made the night unforgettable, though, was Cassadee’s personality. At one point she noticed a fan eating fries and casually took one mid-conversation, sending the room into laughter. Later, after a streak of heartbreak songs, she joked that the night had turned into a “man-hating” show, a moment that perfectly captured her playful, unfiltered charm.


Her storytelling between songs was just as compelling as the music. She opened up about her creative evolution, the freedom she’s finding now, and the journey between who she used to be and who she’s becoming. For us at Soundcheck, we could feel the authenticity in every word she spoke. You could feel the crowd did too. It’s one of the reasons we love Cassadee.


Cassadee Pope plays acoustic guitar on stage with wooden pallet backdrop. Grayscale image, calm and focused atmosphere. Microphone and water bottle visible.
Cassadee Pope performing at City Winery in Philadelphia, PA - Photo by Rebecca McDevitt (IG: @rebeccajeanlimitedphotography)

Cassadee Pope’s run of acoustic shows is a reminder that the power of connection, nostalgia, and a good story can still have an incredible impact.



Comments


SoundCheck Mag - Logo
  • Instagram
  • Facebook
  • Twitter
  • LinkedIn
  • TikTok

© 2025 Soundcheck Mag LLC. All rights reserved.

bottom of page