Challenge Mania Live 2026

Brings Cara Maria and CT Home to Boston!

On Saturday, May 23, 2026, Challenge Mania Live 2026 lands at City Winery Boston, bringing two of the most recognizable faces in Challenge history back to where it all started. Cara Maria Sorbello and Chris CT Tamburello are both Boston natives who took their journeys far beyond the city. This night brings them back in front of a hometown crowd for something personal, loud, and unforgettable.

Boston is getting a homecoming moment.

This special edition of Challenge Mania Live centers on Cara Maria’s 40th birthday and features a full live roast, Boston style. Cara takes the stage knowing exactly what she signed up for, with friends, castmates, and longtime rivals ready to tell stories the cameras never caught.

CT will be in the building as well, returning to Boston alongside Cara for a night that blends humor, history, and shared roots. Mark Long joins the lineup, with additional surprise guests expected to make appearances throughout the night.

The show is hosted by Derrick Kosinski and Scott Yager of the Challenge Mania podcast, who guide the crowd through an interactive live experience filled with laughs, behind-the-scenes moments, and fan-favorite memories from across the Challenge universe. This is not a sit-back-and-watch kind of night. Boston energy is part of the show.

You do not want to miss this event

After the main event, VIP ticket holders are invited to an exclusive post-show Meet and Greet. Fans will have the chance to meet Derrick, Scott, Cara Maria, CT, and other cast members, take photos, ask questions, and connect in a more personal setting. VIP guests will also receive exclusive giveaways, including a limited edition Challenge Mania Boston poster available for autographs.

Two VIP ticket options are available. Stage Premier VIP tickets are extremely limited and include front row seating, early Wave 1 access to the Meet and Greet, and additional exclusive Challenge Mania collectibles. Regular Premier VIP tickets include Wave 2 Meet and Greet access shortly after.

For Boston fans, this night is more than a live show. It’s a return. Two hometown competitors, years of history, and a city that helped shape them welcoming them back.

GET TICKETS NOW!

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