Few destinations in Wisconsin celebrate music quite like Waukesha. Known as GuitarTown and recognized as the birthplace of legendary guitarist and inventor Les Paul, Waukesha has earned a reputation as a place where music is woven into the community year-round.

From intimate acoustic performances overlooking Pewaukee Lake to nationally recognized artists filling Milwaukee arenas, live music is always within reach when you stay at The Ingleside Hotel. Whether you're planning a weekend getaway, attending a concert, or simply looking for a memorable night out, our central location makes it easy to experience the best live music venues, festivals, and outdoor concerts throughout southeastern Wisconsin.

Discover GuitarTown™

No music-focused visit to Waukesha is complete without exploring historic Downtown Waukesha, where the legacy of Les Paul continues to inspire musicians and visitors alike.

Throughout the year, downtown hosts a variety of concerts, community events, open mic nights, and live performances. During the warmer months, the Les Paul Performance Center becomes the heart of the local music scene, welcoming artists and audiences for outdoor performances in a beautiful riverside setting. The annual GuitarTown Music Festival further celebrates Waukesha's rich musical heritage while showcasing talented Wisconsin artists.

Music fans can spend the day exploring local shops and restaurants before enjoying an evening performance, creating the perfect outing in one of Wisconsin's most vibrant downtown districts.
 

Where to Find Live Music in Waukesha County

One of the best things about the local music scene is that live entertainment can be found almost every night of the week. Throughout Waukesha County and Lake Country, restaurants, breweries, waterfront venues, and neighborhood gathering spots regularly feature talented regional musicians.

Popular venues include:
•    Raised Grain Brewing Co. – A favorite for craft beer, outdoor gatherings, and rotating live music performances.
•    Mainstream Bar & Grill – A downtown Waukesha staple known for live bands and energetic entertainment.
•    Artisan 179 – Located overlooking Pewaukee Lake, this restaurant frequently features live music on its patio during the summer months.
•    Curly's Waterfront Sports Bar & Grill – Enjoy live entertainment paired with waterfront views on Pewaukee Lake.
•    Club 400 Bar & Grill – A long-standing local venue offering live music and open mic opportunities.
•    Maddy's Bar & Music Lounge – One of downtown Waukesha's newest destinations dedicated to live music and local talent.

Because performances change throughout the year, there is always something new to discover when visiting the area.

Signature Music Events Worth Planning Around

Every season brings opportunities to experience live music, but several annual traditions have become local favorites.
During the summer, Friday Night Live transforms Downtown Waukesha into an outdoor music festival every Friday evening, featuring multiple stages and free performances throughout the downtown district.
Nearby, Waterfront Wednesdays in Pewaukee offer music with scenic lake views, while Tribute Tuesdays at the Les Paul Performance Center celebrate the music of legendary artists.

No conversation about Wisconsin's music scene would be complete without Summerfest, held annually on Milwaukee's lakefront. Known as the World's Largest Music Festival, Summerfest attracts nationally recognized artists across multiple stages and genres, making it a must-visit event for music lovers visiting southeastern Wisconsin.

Visitors can also enjoy one of our own favorite summer traditions: Music on the Lawn. This free outdoor concert series features local musicians, food trucks, lawn games, refreshing beverages, and family-friendly fun in a relaxed outdoor setting. It's the perfect way to enjoy a Wisconsin summer evening without ever leaving the hotel property.
 

Major Concert Venues Just Minutes Away

Looking for big-name performers or arena tours? The Ingleside Hotel provides convenient access to many of southeastern Wisconsin's premier concert venues.

Within approximately 20 to 30 minutes of the hotel, you'll find:
•    American Family Field – Home to major concert tours and special events.
•    The Rave / Eagles Club – One of Milwaukee's most iconic live music venues featuring rock, country, alternative, and touring artists.
•    Fiserv Forum – Hosting some of the biggest names in music and entertainment.
•    The Pabst Theater Group – A collection of historic Milwaukee venues offering an exceptional lineup of concerts, comedy, Broadway productions, and live performances in unique and memorable settings.
•    American Family Insurance Amphitheater – Located on Milwaukee's scenic lakefront, this world-class venue welcomes chart-topping artists and serves as the marquee stage for Summerfest and other major concerts.

Whether you're attending a sold-out arena show or discovering an emerging local artist, you'll find exceptional entertainment options nearby.

Stay Close to the Music

Conveniently located in Pewaukee just off I-94, The Ingleside Hotel places guests at the center of southeastern Wisconsin's thriving entertainment scene. From GuitarTown and the lakeside communities of Lake Country to Milwaukee's world-class concert venues, unforgettable live music experiences are never far away.
Whether your playlist includes acoustic performers, tribute bands, country favorites, classic rock legends, or today's biggest touring artists, The Ingleside Hotel is the perfect place to stay while exploring the soundtrack of Wisconsin. Book your next getaway today.