Maddy’s Bar and Music Lounge

06/18/2026

💋 It's Ladies Night at Maddy's!! Saturday June 20th @ 9PM!! 💋
🪩feat. Beats by .esofresh
🍒 $3 Bill & Cherry Bombs
🥃 $3 Ole Smoky Shots
👑 $5 Crown
🍋‍🟩 $5 Patron
💘 PLUS free Pink JELLO Shots at Midnight!

06/18/2026

💋🎸 Pretty When She's Angry returns to Maddy’s tomorrow at 8PM!! 🎉 Pop & Rock hits across the decades, come party with us after Friday Night Live!

Let’s summer, Waukesha! See us Friday June 19 At Maddy’s for rock and pop hits from across the decades.

6/19: Pretty When She’s Angry Rocks at Maddy's

Playing 8-11:30 with a small break. $5 cover. 💋

06/15/2026

☀️🎉 Big Summer Fun at Maddy’s!! 🌴Check out our new Summer Cocktail Menu!!☀️🍸

🧡Service Industry Mondays just got even better! 🍇🍓BOGO beers & seltzers now kick off at 2pm! 🍺 Stop in & say hi to Ray today!!

🎯 Tuesdays are for throwin’ DARTS! 🎯 50¢ games ALL day + drink deals you’ll love!! 💙
🍺 $2 Tall boys
🔥 $3 Fireball
🍹 $5 Rail Dbl Talls
🍋 $6 John Daly's

🎱 Wednesdays = Free POOL🎱 The fun starts at 2pm, so grab your friends & come play all night!
🍺 $1 off Tap Beer
🔥 $3 Ole Smoky Whisky
🍉 $5 High Noons
🥃 $7 Jack Dbl Talls

06/13/2026

🎶🎸 Make sure you check out GuitarTown Music Festival today at Cutler Park!!
✨ This FREE Waukesha Event is being put on by our very own Sound Check Entertainment and Studios, who coordinates & books all our live music!!
🔥 We are so excited for GuitarTown Music Festival, we want to keep the party going with Regenerated at 8pm, so please enjoy no cover charge for anyone coming from the event!!

This Saturday, June 13th, the spirit of innovation returns home for the inaugural Guitar Town Music Festival.

We’re celebrating the life and "magic" of our very own legendary Wizard of Waukesha—Les Paul.

The event will take place in Cutler Park from 12pm-8pm with free admission and includes:
🎸Live Music
🎸Instrument Petting Zoo
🎸Exhibits & Eats
🎸and more!

Details: https://www.waukesha-wi.gov/guitartown-music-festival.php

06/11/2026

🎶🔥 Stop out Saturday June 13th at 8PM for REGENERATED!! 🎸🎶

06/10/2026

🎶 Live Music at Maddy's this Weekend! 🎸
🪕🎵 Friday Night 6/12 Nicholas Goeman Band is bringing country to Maddy's with his high-energy, original show!!🍻
🔥 Saturday Night 6/13 Regenerated returns to ROCK Maddy's with 90-00s alt-rock fan favorites!!
📆 As always, a HUGE thanks to Sound Check Entertainment and Studios for booking all our live music!!

06/07/2026

🚨 Come Join Maddy’s Team this Summer!! 🚨
🍻 We are looking for an experienced bartender to bring on at Maddy’s part time!! 🍻
☀️ If you have mad cocktail skills, great ideas & a super fun personality, we want you to bartend for Maddy’s! Required shifts are Sunday 11am til 5pm + a few Weekday Happy Hour shifts (10-15 hours per week)! ☀️ l
Our bartenders primarily work independently, so a City of Waukesha bartending license is required!

06/07/2026

🎸🎶 Come Celebrate 10 Years with Ten Feet Tall Tonight at 8PM!! 🎉

Setting up and getting ready to rock 10 years of Ten Feet Tall! Maddy’s Bar and Music Lounge

06/05/2026

☀️🎶 Friday Night Live kicks off tonight!! Stop by Maddy’s for the after party!! 🎸
🍻 Get loud & rowdy w/ Sweet Nothings. at 8PM!!
🎉🔥 Saturday Night Ten Feet Tall celebrates their 10 YEAR ANNIVERSARY!!!!!! 🥂🎂 + there will be cake! + 4 new songs!! + surprise guest!! 🎸🎶