On Halloween night at Chez Est, the stage belongs to the audience. The Wethersfield Avenue bar and cabaret holds its Annual Halloween Costume Contest on Saturday, Oct. 31, 2026, running from 8 p.m. to midnight, and the marquee name on the flyer is not the point of the evening so much as the bait. Loosey LaDuca, who competed on Season 15 of RuPaul's Drag Race, headlines. The crowd supplies the show.
Three cash prizes go to the best costumes in the room: $250 for first place, $150 for second, $100 for third. It is a general-admission club night, no reserved seating, the kind of evening where the judging happens in the same room where people have been standing since the doors opened.
That a Hartford bar can book a Drag Race alum for a Halloween party is a fairly recent development, and it says something about how quickly the local drag scene has moved. When Season 15 of RuPaul's Drag Race premiered in January 2023, it introduced three Connecticut queens at once, and not a single Connecticut-based performer had competed in the previous fourteen seasons. Loosey LaDuca, from Ansonia, was one of the three, alongside West Hartford's Amethyst and Hartford's Robin Fierce. All three had performed at Chez Est.
"What's really great about Connecticut drag queens is that there are so many different styles," LaDuca told the Hartford Courant that January. "We do it all here."
LaDuca, whose name offstage is Timothy P. Rinaldi, grew up in Ansonia, attended Ansonia public schools and did musical theater in high school, and was working as a construction worker in his hometown when the season was announced. The day-job detail became one of the season's early talking points. So did the name itself: Loosey LaDuca is a nod to Lucille Ball, and the performer has said the reference is deliberate, a tribute to a performing idol.
On the season premiere, LaDuca volunteered to sing live rather than lip-sync, a risk taken to stand apart from the field. The judges, Ariana Grande among them, were not won over by the vocal, and the episode ended with LaDuca in tears but still in the competition. LaDuca had won the photo-shoot challenge earlier in the same episode, posing glamorously on a motorcycle while a fan blew feathers into the contestants' faces. The season went on to produce one of the more durable artifacts of recent Drag Race memory: an original song called "Let Loose," which went viral and later got a remix featuring Jan Sport and Lemon.
That is the résumé arriving in Hartford on Halloween. But the venue is the other half of the story, and arguably the older one.
Chez Est describes itself as Hartford's only LGBTQ+ restaurant, bar and cabaret, and as having served the community for roughly half a century; its own materials put the number at over 49 years, and the state tourism office's listing rounds it to 50. It sits at 458 Wethersfield Ave., a two-story building that glows red, blue and purple at night, in the city's South End. Over the decades it has been a bar, a restaurant and a performance space at once, and it has been through a renovation in recent years that regulars describe in superlatives: a professionally lit stage, a VIP lounge, a fenced outdoor patio, gender-neutral bathrooms, a coat check, a parking lot that fills on big nights and free street parking on Meadow Street when it does.
The club's identity is bound up with drag as an institution rather than a novelty. Its House of Legends competition, now in its sixteenth season as of December 2025, is one of the state's longest-running drag contests; when it crowned a winner that month, the evening was hosted by Vu Tran, an emperor of the Imperial Court of Connecticut, with Chez Est owner John Pepe on hand. The House of Legends roster reads like a local hall of fame, and LaDuca's name sits on it alongside Amethyst, Robin Fierce and a long list of Connecticut performers who built careers on that stage before television came calling.
Which is why a Halloween costume contest here is not quite the disposable party it might be elsewhere. The bar has spent decades building an audience that knows how to dress, and a cash prize for the best costume is a way of turning the room into the lineup. The headliner gets a set; the crowd gets a contest; the two run into each other somewhere around midnight.
Details beyond the date, time and prize amounts are thin on the public record. The CTvisit listing, which is the event's primary public announcement, does not state an admission price, and Chez Est's own events calendar is rendered dynamically in a way that resists outside verification, so the ticket cost for the 2026 edition could not be confirmed independently. The club sells tickets online and asks that guests present a state-issued ID or passport in its original form regardless of age; photocopies and phone photos are not accepted, and a paper copy is allowed only if it is the original from the DMV. Anyone planning to compete should check chezest.com or the bar's social accounts for door times and cover before heading to Wethersfield Avenue.
What is not in doubt is the shape of the night. A drag cabaret that has outlasted most of the institutions around it, a Connecticut queen who went from construction sites in Ansonia to national television, and a room full of strangers in costume competing for $250. The contest is annual, the prizes are cash, and the judging, as ever, is by whoever shows up.