Challenge Mania Live City Winery Tickets - May 22nd, 2026

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Concerts > Comedy > Challenge Mania Live Boston Tickets > City Winery - Boston > Challenge Mania Live May 22 2026 Tickets

Jon Butcher at Middle East - Downstairs
Jun 5 - 08:00 PM – $98+
Greg Mendez at The Sinclair Music Hall
Jun 26 - 08:00 PM – $56+
bixby at The Sinclair Music Hall
Jun 28 - 08:00 PM – $60+
Haute & Freddy at The Sinclair Music Hall
Jun 1 - 08:00 PM – $98+
Bailey Katsu at Middle East - Upstairs
Jul 17 - 08:00 PM – $88+
Gorillaz at TD Garden
Oct 1 - 07:30 PM – $94+
Phish at Fenway Park
Jul 31 - 03:30 AM – $80+
Stephen Lynch at City Winery - Boston
Jun 3 - 07:30 PM – $76+
The Guess Who at Leader Bank Pavilion
Jul 17 - 07:30 PM – $71+
Southern Culture On The Skids at City Winery - Boston
Sep 29 - 06:30 PM – $64+
Challenge Mania Live
May 22 - 07:00 PM – $55+
City Winery
May 22 - 07:00 PM – $94+
Challenge Mania Live: The Roast of Cara Maria
May 23 - 07:00 PM – $94+
Pink Martini
May 23 - 07:30 PM – $59+
Roberto Carlos
May 23 - 08:00 PM – $83+