Plymouth High Drama Presents Four Shows Nov. 5–8
Plymouth High School’s student production runs Nov. 5–8, with three evening performances and a Sunday matinee. Reserved seats cost $11 and are sold online through GoFan.
Entertainment
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Ruthie & The Ramblin’ Kind Play Paradigm in Sheboygan Saturday, Oct. 24
Ruthie & The Ramblin’ Kind play Paradigm Coffee and Music in Sheboygan at 7 p.m. Saturday, Oct. 24. Tickets are $10 presale or $15 on show day.
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Weill Center Ghost Tours Set for Oct. 28, 30 and 31 in Sheboygan
The Weill Center’s Specters of the Spotlight tours offer four start times across three dates. Tickets are $20 per person plus fees, with advance registration required.
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Rebel Reels announces 2026–27 film season at Paradigm in Sheboygan
Rebel Reels opens its four-film season October 23 at Paradigm, with Night of the Living Dead, a holiday screening of The Apartment and two films in 2027.
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Five Sheboygan County Events for Saturday, Oct. 10, and Sunday, Oct. 11
From a craft fair and museum activity to two Saturday performances and a Sunday garden event, these five options span Sheboygan Falls, Kohler and Sheboygan.
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Free Belle Weather Concert Set for Oct. 15 in Sheboygan
The Belle Weather brings acoustic music and storytelling to Downtown 925 on Oct. 15, from 6 to 8 p.m. Admission is free; Pelican Room dining seats are limited.
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Boo Trivia Fundraiser in Sheboygan Falls October 16
Sheboygan Theatre Company hosts Boo Trivia at Fat Cow in Sheboygan Falls on October 16, 2026. Teams of four can compete for $150; entry is $40 per team.
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Sheboygan Film Festival to Screen Homegrown Superhero Film ‘SHANK!’ at Jake’s Cafe
The October 3 screening will include a conversation with filmmakers and a discussion led by UW-Green Bay film professor Zack Kruse. A superhero-adjacent independent film with deep roots in collaboration is coming to the Sheboygan Film Festival. SHANK! will screen…
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Sheboygan River Fest Brings Music, Food Vendors and Family Activities September 19
Free River Fest is scheduled for Saturday, September 19, along Sheboygan’s Riverfront Drive Boardwalk with live music, children’s activities, vendors, food trucks and boat tours.
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Sheboygan Film Festival Set for October 1-4 With Family Programming
The second annual Sheboygan Film Festival runs October 1-4 across Sheboygan, with opening-night plans, pass choices, individual tickets and family programming.
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3 Sheeps Combines Oktoberfest and Strongman Competition for Hulktoberfest September 5 in Sheboygan
Hulktoberfest is planned for Saturday, September 5, at 3 Sheeps Brewing in Sheboygan with Oktoberfest activities, food, music, beer and a five-event strongman competition.
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175th Sheboygan County Fair Set for Sept. 3–7 in Plymouth
The 175th Sheboygan County Fair runs Sept. 3–7 in Plymouth, with carnival rides, grandstand shows, family activities, a free shuttle and planning details.
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Random Lake to Host Free Sunshine Shakedown Festival August 29
Random Lake’s Artfully will host a free August 29 music and maker festival with live bands, artisan vendors, tie-dye, food and themed drinks.
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Free Levitt AMP Concert Brings Plenazo Tribe to Sheboygan City Green on August 13
Plenazo Tribe will perform free Puerto Rican plena music at Sheboygan City Green on Thursday, August 13, with art activities, food trucks, and a beverage tent.
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Free Paine Street Ramblers Concert Set for August 16 at Kohler’s Waelderhaus
The Paine Street Ramblers will perform free New Orleans jazz and Dixieland music at 2 p.m. Sunday, August 16, at Kohler’s Waelderhaus.
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Free Levitt AMP Concert Returns to Sheboygan City Green August 13
Plenazo Tribe will perform Puerto Rican plena at a free, family-friendly Levitt AMP concert Thursday, August 13, at City Green in Sheboygan.
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Bubble Bash Brings Giant Bubbles and Dance Party to Sheboygan City Green August 12
Mead Public Library will host Bubble Bash at Sheboygan City Green on Wednesday, August 12, with Marvelous Michelle and hands-on bubble activities.
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Free Paul Todd Jr. Concert Set for August 7 at Generations in Plymouth
Generations in Plymouth will host a free Paul Todd Jr. concert Friday, August 7. Doors open at 5 p.m., with an optional $30 dinner buffet requiring advance registration.
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Weill Center to Host ‘LEGENDS!’ Music Revue in Sheboygan August 13
Pankratz Arts Exchange will bring its ‘LEGENDS!’ music revue to the Weill Center in Sheboygan on Thursday, August 13, with vocals, dance and aerial performances.
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Saturday, August 1, 2026: Brat Days at Kiwanis Park — NWS Forecast Calls for Morning Showers, Scattered Afternoon Rain
Brat Days returns Saturday, Aug. 1 to Kiwanis Park with free entry and music. NWS says morning showers, 90% afternoon chance—pack rain gear.
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