A sea of people dressed in sailor and clown-inspired outfits surges towards the front gates with their tickets ready. The dark night sky contrasts with the glowing white tented amphitheater. Screens outside of the venue display a name that had fans ecstatic for the night: Conan Gray. Although his breakout song, “Heather,” wasn’t trending until 2020, he’s been building up his pop career since he was 12-years-old. His first single was released in 2017, and since then, he has created four studio albums. Gray’s most recent record, Wishbone, was announced in May 2025 and released in August. From performing “Vodka Cranberry” at the MTV 2025 Video Music Awards to having Wishbone debut at No. 1 on the Billboard Top Album Sales chart, this era has been full of growth and recognition for the artist. His recent tour, The Wishbone Pajama Show, took place in September and October 2025 in North America. I am so grateful to have gotten to see Gray perform in Bridgeport, Connecticut, at the Hartford Healthcare Amphitheater on Sept. 19, 2025. Both Gray and his opener Hemlocke Springs transformed the venue into a comforting home, where everyone became a family bound by their emotions and experiences.
Hemlocke Springs
As the time ticks down to the start of the concert, fans rush around the venue as they prepare for the show. They take selfies with their friends in front of the stage, grab some of the newest tour merch, enjoy a snack, trade bracelets, and rush to clear out their phone storage so that they can take photos of the show. The background music cuts out suddenly — the concert is officially starting. Fans jump out of their seats and press forward suddenly, cheering loud enough for people outside the venue to hear them. The lights on stage glow, revealing Springs and her band members. Kicking off the night with her high-energy song “heavun,” Springs has the crowd dancing and moving immediately. Not only are her songs fun and bold, but her outfit reflects her style perfectly with red bows and a flowy tutu-like skirt. She twirls across the stage during songs such as “enknee1,” connecting with the attendees no matter where they are in the crowd.
The venue continues becoming more packed as Springs’ set continues. Her liveliness never falters, and the crowd matches her spirit with every tune. Springs even surprised fans with unreleased songs such as “head, shoulders, knees and ankles.” Her band members, Victoria Aycock on the keys and April Lee on the drums, join in and sway to the beat of each song, like as “girlfriend,” Springs’ most popular song. The room becomes an ocean of hands waving back and forth. As this rising artist’s set ends with “sever the blight,” she takes in the sight of such a large community before her. Springs prepared fans for the thrilling and emotional night that was to come, fueling them before the main set.
It’s Conan Gray’s World
The random conversations that sparked after Spring’s set soon disappear as the crowd sings along to “bad idea right?” by Olivia Rodrigo, one of Gray’s close friends. As soon as the lyrics “now I’m gettin’ in the car, wreckin’ all my plans / I know I should stop” play over the speakers, everything goes dark, and the venue erupts with screams of anticipation. Blue lights illuminate the amphitheater, and the words “The Wishbone Pajama Show” appear behind Gray’s band. Then the phrase “I / a wishbone never breaks even,” shines on the screen to start act one of the setlist. Gray pedals onto the stage on a bicycle, opening a mailbox labeled “Bridgeport, CT 9/19/25” to retrieve his microphone. Fans grip the barricade for support as tears of joy glisten in their eyes, their cheers echoing throughout the tented venue as they sing along to “My World” from Wishbone. Gray scampers across the stage with a smile that mirrors the ones his fans have, climbing onto a windmill prop and spinning in circles with his sailor cap ribbon flowing.
While this tour is meant to celebrate songs from Wishbone, Gray keeps the show’s attendees on their toes by singing tunes from his other albums. “Never Ending Song” and “Bourgeoisieses” from Found Heaven, as well as “Wish You Were Sober” from Kid Krow follow shortly after the opening song. Jaws drop in surprise as fans sing along, knowing the lyrics by heart. Soon, Gray departs the stage as the phrase “II / i got the short end of the stick” appears on the screen. A bed prop is moved into the spotlight as the artist reappears, wearing a vibrant, sparkly blue pajama set and singing “Class Clown.” The next song, “People Watching” from the album Superache, is a fan-favorite that has the crowd singing with every ounce of emotion they have. From the fans waving their phone flashlights to “The Cut That Always Bleeds” to the touching guitar moments in “Eleven Eleven,” Act II ends with friends clinging to each other and strangers comforting one another.
New Songs and Memories
The next segment of the show begins with “III / i took the long way to realization” glowing on the screen. Conan Gray appears in a new flowing white and blue outfit, singing “Romeo” while standing in a wooden boat on stage. Partway through Act III, Gray announces that he would have someone in the crowd help him pick the next song (his version of a surprise song). This lucky person was NFL player Carl Nassib. The fan chosen usually must break a wishbone with Gray. If they get the long end, they get to get to pick the song. At this show, though, Gray and Nassib get equal parts of the wishbone. Nassib doesn’t just choose any song to have performed next: he chooses “Care” (instead of Sunset Tower), a song that had not been sung live until then. Fans scramble to start their videos, looking at each other with shock reflected in their glossy eyes. This reflective high of the night continues with multiple memorable moments during tunes such as “Heather” (the version with the lost verse) and “Connell,” as the feeling of being home takes over the venue.
“IV / i wished for love, and i found it” appears before “Actor” begins, with the crowd raising their voices to scream the bridge of the tune. After Gray introduces his talented all-female band, the atmosphere shifts for “Maniac.” Fans dance throughout the amphitheater, with the jewels on their faces and sparkles on their clothes reflecting the flashing lights. Gray seems to end the night with “Vodka Cranberry,” leaving the crowd shocked by both his high note and how quickly the show seemed to end. However, they don’t have to wait long for a sudden encore. Conan Gray returns to the stage to the roar of the crowd, wearing a blue military-inspired uniform outfit. “Memories” hits fans hard, as they remember both the hard times in their lives as well as the beautiful moments (such as this concert). Stars and glowing orange lights brighten the venue as Gray performs “Caramel” from Wishbone, leading fans to wave their hands back and forth as one big family. The concert comes to an end, as Gray tells the crowd that he loves them before skipping off stage while waving to the entire venue.
The venue lights abruptly turn on to the dismay of the attendees. Friends and loved ones hold each other tight, and people who just met at the show exchange social media handles to stay in touch. Fans take last-minute photos in front of any Conan Gray signs, pick up last-minute merchandise, and head out to find their cars. Constant chatter fills the venue as people talk about the new songs, seeing certain outfits, and experiencing something that they’ll never forget.
While wishbones and angel numbers may be lucky for some people, everyone who saw Gray and Springs perform felt luckiest of all. The amphitheater in Bridgeport wasn’t just a venue; it was a home that felt safe, comforting, and uplifting, all at the same time. Every song led to new emotions and memories. Even if you’re feeling left out after not attending this past tour, don’t be worried, since Gray will be visiting even more locations for “The Wishbone World Tour” in 2026, in North America and beyond. You might be a fan of every album by Conan Gray, or just nostalgic about “Heather,” but the magic of his music knows no boundaries and might help you feel and heal. Be sure to check out his newest album, Wishbone, and sail out to a future show!