Entertainment events in Waukesha

• Sat, 14 Feb, 2026 - 08:00 PM

  💘 Smart Mouth returns to Maddy's Waukesha Valentine's Day SAT 2/14 - New.Gen Line-Up Reveal! 🚀

  Maddy’s Bar and Music Lounge

  146+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Old School Favorites Adult Skate (16+)

  Waukesha Skateland

  112+ Interested
• Fri, 13 Feb, 2026 - 05:00 PM

  The Dark Romance Ball

  Milwaukee Marriott West

  USD 142
• Sat, 31 Jan, 2026 - 08:00 PM

  Slow Jams Adult Skate (16+)

  Waukesha Skateland

  94+ Interested
• Sat, 11 Apr, 2026 - 07:00 PM

  The Ultimate Ozzy Experience - Madman's Diary

  Waukesha County Expo Center

  138+ Interested
• Sat, 24 Jan, 2026 - 07:00 PM

  Indigo Canyon Live At Let It Be in Waukesha WI

  716 Clinton Street, Waukesha, WI, United States, Wisconsin 53186

  49+ Interested
• Sat, 24 Jan, 2026 - 09:30 AM

  K-Pop Demon Hunters Skate Party

  1931 E Main St, Waukesha, WI

  106+ Interested
• Wed, 21 Jan, 2026 - 07:00 PM

  Jazz Wednesday's ft. JZ Jazz Trio

  716 Clinton Street, Waukesha, WI, United States, Wisconsin 53186

  11+ Interested
• Sat, 31 Jan, 2026 - 05:00 PM

  PRODIGAL SONS @ SALTY TOAD!

  Salty Toad

  18+ Interested
• Thu, 19 Feb, 2026 - 07:30 PM

  CARMEN NICKERSON with special guests KOSTIA & STAS - A Mainstage Guest Act

  264 W Main St, Waukesha, WI, United States, Wisconsin 53186

  11+ Interested
• Fri, 27 Mar, 2026 - 08:00 PM

  3/27: Pretty When She’s Angry Rocks at Maddy's

  Maddy’s Bar and Music Lounge

  15+ Interested
• Sat, 17 Jan, 2026 - 07:00 PM

  Heather Mall Album Release Show

  716 Clinton Street, Waukesha, WI, United States, Wisconsin 53186

  21+ Interested
• Sat, 07 Mar, 2026 - 08:00 PM

  Ten Feet Tall at Maddy's

  Maddy’s Bar and Music Lounge

  127+ Interested
• Sat, 21 Feb, 2026 - 05:00 PM

  8th annual shrimp boil

  Waukesha Masonic Lodge # 37

  32+ Interested
• Mon, 16 Feb, 2026 - 07:00 PM

  AUDITIONS - GIVE ME MOONLIGHT, A Black Box Production

  264 W Main St, Waukesha, WI, United States, Wisconsin 53186

  10+ Interested