For the album, each band member chose one song to cover. The group's cover of Wilco's "Reservations" was chosen by Matthew McCaughan.
Kurt Wagner says of the cover, "As with all the covers on TRIP it was chosen not so much for it's content or as a tribute to the original but for what our group could bring out in the recording of it. In this case I think it best demonstrates who we are as a group and what we are currently capable of expressing."
McCaughan explains, "I’d like to say that Wilco’s "Reservations" is a song I’ve always wanted to cover. But honestly, after a friend had mentioned it in a story, I had to go back and give it another listen. Picking out a cover is stressful for me. It’s kind of a dumb thing to stress about, but so many songs have memories tied to them, and I don’t want to cloud those memories. I usually pick one of those songs that I feel would fit the band, but then I go back and forth, wondering the best way to approach the arrangement. Should we honour the original and try to faithfully re-create all the sounds and performances that make the song special to me, or should we take it apart and start over?"
He continues, "Then, add in the fact that the cover would be recorded and preserved forever. I could not think of one song that I couldn’t make an argument for both approaches, so it always ends in a one-person stalemate. So I decided I would pick a song that, while I love it, and know it, it wasn’t one that had been on repeat for months at some point in my life, nor was it one that is permanently tied to some memory of my own. Instead, I used my family’s and friends’ collections and recollections with and without their permission. That way I’d just ruin it for them. But it’s the thought that counts."
TRIP was recorded at Battletapes in Nashville, TN across five days in December 2019. The LP is produced, engineered and mixed by Jeremy Ferguson (apart from "Reservations" which was co-mixed by Ferguson and McCaughan).