Live music in Sheboygan, WI

The Plymouth Arts Center is hosting its annual Paint the Towns in Fall Color, en Plein Air competition and exhibition, featuring outdoor painting. Artists will have painting days running across locations in Plymouth, Greenbush, and Glen Beulah, with an extra paint weekend on the Road America grounds. A public reception, awards ceremony, and silent auction will be held at the Plymouth Arts Center on Friday, October 20, from 6:00 PM to 9:00 PM, with live music and complimentary appetizers and desserts. The artwork will remain on display in the Gallery 110 North through November 17, 2023, with unsold pieces available for purchase via a “Buy it Now” retail price.

Beacon On The Rocks hosts live music every Friday, featuring local Wisconsin musicians performing a mix of country, rock, folk, and popular music. Enjoy the lakeside setting with a drink or a bite to eat while the music plays.

HOGGFest brings live music, tasty eats, and family fun to Veterans Park in Oostburg. Three bands take the stage during the event, featuring The Noah Nelson Band, The Nate Bjorge Band, and Juice's Midnight Preachers. Food highlights include Heavy Smoker's BBQ Truck with a pig roast and a Dirty Soda Stand, along with additional options. Kids can enjoy a dedicated zone with bounce houses and other activities. If weather does not cooperate, everything moves indoors. This fundraiser supports the H.O.G.G. area youth group, representing the Hingham, Oostburg, Gibbsville and Cedar Grove church area youth groups, as they work toward a faith-focused trip to Ravencrest in Colorado next summer. Community sponsorship helps make it happen, with Oostburg Family Dentistry as the main event sponsor, Advanced Comfort supporting the Kids Zone, and further backing for Juice's Midnight Preachers from Dirkse & Huibregtse, GK Machine, Oostburg Family Dentistry, Pleasant View Trees, and Sargento Cheese. The Dirty Soda Stand receives support from Bliffert Oostburg Lumber & Design, Buyze & VerVelde Concrete, Cedar Valley Cheese, Culver's, Mike DePagter Plumbing LLC, Luedtke Electric, Nyhof, Ongna Wood Products, Oostburg Automotive, Oostburg State Bank, Silver Services, Stecker Construction, Steve Rogers Painting, United Building Supply, Inc., and Wenig Funeral Homes, with additional general sponsors including Auto Enterprises, Grandview Lawns, Hopeman Carpentry, Jacoby's Autobody, Lakeland Chiropractic, and Plus Group Wealth Advisors.

Backstage Pass brings a solo show to Blue Harbor Resort & Conference Center that delivers the punch of a full band, blending popular rock and country tunes into a high-energy set filled with sing-along moments. Promoted as Wisconsin’s favorite one-man band, this performance leans into a party mood with loud music, cold drinks, and good vibes shared with friends.

Sing your favorite songs at Uncle Gunter's, a cozy spot with Wisconsin charm, craft cocktails, and satisfying food. Enjoy an old fashioned, pair it with a gourmet panini or cheese curds, and unwind in a welcoming atmosphere while taking your turn at the mic.

Join the Sheboygan Ukulele Club and Lil' Rev for a free-form get-together for ukulele fans. Bring your ukulele (or a similar instrument) if you’d like to work on a new song or a new skill. All experience levels are welcome. Meeting locations for the summer may vary, so check the Uke Club Facebook page for the most up-to-date spot.

On summer Tuesday evenings, 8th Street transforms into an open-air dining experience with dishes from restaurants around the city and performances by local musicians. Attendees can sample a variety of cuisines while taking in a lively atmosphere that highlights Sheboygan’s culture. It offers residents and visitors a relaxed way to experience the heart of the city through food and music.

The Plymouth Arts Center is hosting its annual Paint the Towns in Fall Color, an outdoor plein air painting competition and exhibition. Midwest artists can register in advance for a chance to be accepted, then paint during the designated outdoor painting days around Plymouth, Greenbush, and Glen Beulah, with an additional paint weekend invitation on the grounds of the Road America racetrack. A public reception with live music, complimentary appetizers and desserts, and a silent auction will be held at the Plymouth Arts Center on Friday, October 20 from 6:00 PM to 9:00 PM. The show will remain on display in the Art Center’s Gallery 110 North through November 17.

A family-friendly evening pairs the Summer Concert Series with Community Safety Day at River Park in Sheboygan Falls. Enjoy live music from Past Curfew, browse vendors, and grab a bite from food trucks. Kids can explore public safety vehicles and meet the personnel who operate them. Bring lawn chairs, settle in, and relax at River Park for a lively community gathering.

A cabaret showcasing rising talent from the community, blending a hint of angst with a spark of hope and plenty of skill. The setlist pulls from musical theatre that centers on youthful characters and coming of age journeys, bringing their stories to the forefront. It highlights the passion, energy, and creativity of the next generation through songs that capture raw emotion and forward-looking spirit.

The Plymouth Arts Center is hosting its annual Paint the Towns in Fall Color, en Plein Air (outdoor painting) competition and exhibition. Artists are invited to register in advance, with painting days running across several locations during mid-October, and a special paint weekend on the Road America racetrack grounds. A public reception, awards ceremony, and silent auction will be held at the Plymouth Arts Center on Friday, October 20, featuring live music and complimentary appetizers and desserts.

Celebrate Puerto Rican plena with live music at no charge on Sheboygan’s City Green. The event includes creative activities for all ages, an array of local food trucks, and a beverage tent. Move to the beat and share the experience with friends and neighbors.

A high-energy music revue from Pankratz Arts Exchange features a troupe of singers and dancers performing hits by legendary artists including Elton John, The Beatles, Michael Jackson, Madonna, Taylor Swift, Frank Sinatra and more. The program spans rock and roll, country, pop, jazz and funk, with dynamic acrobatic and aerial performances by Warped Dance Company enhancing the show. Pankratz Arts Exchange is a nonprofit performing arts organization now in its 15th year, dedicated to delivering quality arts education and performance opportunities for all people. This touring season marks a debut across three counties in Wisconsin and follows a long run of music revues, musical theater productions and multi-arts youth camps. Tickets are available in three tiers priced at $47 plus fees, $37 plus fees and $27 plus fees. All sales are final with no refunds, exchanges or weather cancellations. Ticketing is handled through TicketSearch, and there is no affiliation with secondary ticket markets.

Karaoke and music trivia come together at Hika Bay Tavern in Cleveland, Wisconsin. Step up to the mic to sing, then test your knowledge with trivia between songs. While you are there, explore the tavern’s daily specials and enjoy a pizza.