Events in Sheboygan, WI

Participants will gather at St Luke with a bicycle, a helmet, and a water bottle, ready for a fun outing.

Swift Nation brings a high-energy, family-friendly Taylor Swift tribute that spans every era of her music. Created and produced by David Yuter to evoke the live feel of the Eras Tour, the show is led by vocalist Star Melody Ebner, whose background includes work with numerous San Diego bands. Expect detailed choreography, era-specific costumes, a powerhouse band with professional dancers, and original arrangements that pair pop sheen with rock-show punch. Since launching, the production has toured widely with more than 100 performances across over 30 U.S. states, appearing at major venues including Mohegan Sun Arena and the Pacific Amphitheatre, and it is expanding to audiences in Asia, Dubai, and Australia. Tickets are priced from $35 to $79. There are no refunds, exchanges, or weather-related cancellations. Tickets are available exclusively through TicketSearch, and there is no affiliation with secondary ticket marketplaces. Presented by Plymouth Advancement Association and sponsored by Masters Gallery Foods. This performance is an unofficial tribute and is not endorsed by or affiliated with Taylor Swift, TAS Rights Management, or related entities.

The SCIO Sheboygan Summer Farmers Market fills the historic Fountain Park with the flavors and creativity of local producers. Explore in-season fruits and vegetables, locally raised meats, farm eggs, cheese, baked treats, cut flowers, meals from food trucks, and handcrafted goods from vendors located within 100 miles. FoodShare and EBT are accepted at the SCIO information booth, and the Double Your Bucks program offers a daily match up to $20 on fresh fruits and vegetables. WIC and SFMNP vouchers are also welcomed.

Gemstone sluice mining returns to M&T's Gibbsville Orchard with The Tinker Shoppe from Mayville, Wisconsin. Try the sluice to sift through material and keep any gemstones you discover. This hands-on activity is offered on both days of the Annual Harvest Festival and welcomes participants of all ages, with bags available. While there, explore The Tinker Shoppe’s booth featuring unique board games, toys, gemstones, and stone items.

A community-run market in the heart of Oostburg, Wisconsin, created by and for local residents. It takes place on the second and fourth Saturdays in June, July, August, and September. Vendors interested in participating can email shopatmargos@gmail.com to reserve a spot or ask questions.

Mortal Matters is a community book club that explores death, dying, grief, and the broader human experience through shared reading and conversation. It offers a thoughtful space for curiosity, reflection, and candid discussion of subjects that are often hard to talk about. Selections are announced in advance, so you can participate when a particular title or theme speaks to you or attend regularly. The gathering welcomes everyone, with no background or expertise required, only a willingness to listen, reflect, and engage respectfully. Please note that this is a discussion-focused forum for learning and connection, not a grief support or counseling group. Hosted at WordHaven BookHouse.

Sheboygan cover band Nitro Five performs at M&T’s Gibbsville Orchard with a five-piece rock lineup featuring songs by Journey, AC/DC, Cheap Trick, and Blink-182. Families and friends can spend the day picking apples, browsing the gift and bakery shop, and playing outdoor games. Food and beverages are available for purchase. Pets are not permitted, carry-ins are not allowed, and there is no cover charge.

This launch party at Falls Tap centers on a monthly meat raffle that supports Falls Tap and Paws Up Pet Rescue. After the raffle, there will be music and karaoke, chances to enter 50/50 and bucket raffles throughout the day, and information about the upcoming Bingo Pub Crawl presented by 12-Days of Christmas. Falls Tap will serve cold drinks and tasty food. It is a welcoming way to support local efforts while learning about the missions of 12-Days of Christmas and Paws Up Pet Rescue.

This event marks a return performance at a favorite Fall Fest, bringing the energy back to the celebration. Further details will be announced.

Harbor Pointe Mini Golf hosts a community gathering that pairs a round of mini golf with a Down syndrome awareness walk, bringing together families, friends, and supporters from Sheboygan and surrounding counties. Registration covers mini golf at the course, face painting, hands-on crafts, balloon art, a red carpet 21 Showcase celebration, a harbor-side walk in Sheboygan, raffles, snacks, and activities for all ages. Funds raised benefit DSAW, supporting programs, resources, advocacy, and assistance for more than 5,500 individuals with Down syndrome and their families across Wisconsin.

Try your hand at the pottery wheel in a beginner friendly class at MAS Arts Studio. Learn the basics in a supportive setting, explore your creativity, and shape a piece from start to finish. Multiple time slots are available to fit different schedules. You will leave with a handmade work you created yourself.

Myles Wangerin returns to M&T's Gibbsville Orchard after a couple of years for a live solo performance. The singer songwriter and WAMI award recipient brings a solo set on guitar, drawing on influences that include Garth Brooks, Brad Paisley, The Steve Miller Band, and AC/DC. Alongside the music, the orchard offers games, apple picking, a bounce house, and a gift store. Food and drinks will be sold on site. Carry-ins are not permitted, pets are not allowed, and there is no cover charge. Seating is limited, so bringing lawn chairs is encouraged.

Explore the story of one of the nation’s most carefully planned communities in Built with Purpose. The program traces the Village of Kohler from its beginnings, its development in tandem with the Kohler Company, and the people and ideas that shaped its character. With local photographer Darryl Gumm, it spotlights innovative design and a sustained commitment to quality of life, bringing the village’s history and heritage into focus today.

Ecology Outfitters hosts an annual nighttime kayak outing by moonlight. The group launches from Pigeon River Park, follows the Pigeon River to Lake Michigan, and takes in the sounds and sights that emerge after dark. At the lake, participants watch the moon climb above the water, then make the return trip to the launch under a sky full of stars. The cost is $35 per person and includes a kayak, gear, a PFD, and a white light. The participation fee is $10 for those bringing their own kayak and equipment. For safety, a PFD is required and each participant must display a bright white light with a 360 degree beam, mounted on the boat or worn as a headlight. Reservations can be made by texting or calling 920-242-8053.

Experience the Sheboygan River by moonlight with Silent Wake’s yearly series of full moon paddles in Downtown Sheboygan, Wisconsin. Kayaking after dark under a bright moon offers a calm, memorable perspective on the water. Routes are chosen for low boat traffic to support a safe environment, and prior paddling experience is recommended. The pace is relaxed and the group travels together. Upon arrival, participants receive a kayak, gear, and white lights, and staff will help with fitting. Those bringing their own kayak and equipment should have everything unloaded and ready before launch, and the cost is the same whether gear is provided or not. A shore-based safety talk takes place before heading out, and a steady white light remains on each kayak while on the water. Please stay with the group and do not paddle ahead of the designated leader. The cost is $45 per person for each outing. Group size is limited to eight and spots tend to fill quickly. If weather requires a reschedule, notice will be shared on the day of the paddle.

Wisconsin real estate investors and other driven professionals gather for a meetup devoted entirely to building connections. There are no sales pitches, no formal agenda, and no sponsors, just time to network. Attendees include business owners, real estate investors, entrepreneurs, and high performers who value learning from one another and pushing each other to grow. Participants are encouraged to arrive with an open mind and be ready to share what they are working on, what they do best, and where they could use support in their business. The gathering takes place at Field to Fork, with free parking available behind the building. The group meets in the bar area located between Field to Fork and the connected Il Ritrovo space. This series is hosted monthly in Sheboygan and is part of a broader network with additional meetups in Green Bay, Appleton, La Crosse, Delafield, Watertown, and Milwaukee. A Facebook group called Caffeine & Cashflow Business Networking offers updates and a place to connect between events.

Warm up with a one-night stock pot social pop-up centered on fall-inspired soups, stews, and bisques. Each order comes with a generous slice of Oak & Arrow artisan sourdough, and menus feature local meats and produce. An example from last season included sweet corn bisque with chorizo, house jalapeño cheddar cornbread croutons, and green onion. Vegetarian and gluten-free options will be available. Outdoor seating accommodates 20 with ADA accessible spots. If the weather does not cooperate, meals can be packaged to go. Please use street parking.

Double Eagle Mobile Mini Golf LLC sets up at M&T's Gibbsville Orchard with 18 uniquely themed holes for playful head-to-head putting with friends and family. Enjoy food, games, live music, and apple picking while you compete for bragging rights. Outside food or drinks are not permitted, and pets are not allowed.

Brace's Smoke Pit BBQ brings its food trailer to M&T's Gibbsville Orchard from Dodge County, serving wood-fired, low and slow barbecue. The day features family-friendly activities such as 18-hole mini golf, live music, outdoor games, apple picking, and more.

Moon Pool brings a fresh, high-energy rock set to M&T's Gibbsville Orchard, performing familiar favorites with polish and a youthful edge. This up-and-coming band earned a top 10 spot in the 2025 Summerfest Battle of the Bands. Make it a full outing with 18 holes of mini golf, a food truck, outdoor games, tractor wagon rides, apple picking, and more. Please note the following policies: no pets, no carry-ins, and no cover charge.

Try hockey at a free introductory session hosted by the Sheboygan Lakers at the Sheboygan Lakers Ice Center. Boys and girls can step onto the ice, have fun, and get a feel for what the sport is all about. No prior experience is required, just bring enthusiasm and a willingness to try something new.

John McGivern returns with a storytelling performance that explores the seasons of both weather and life. He shares springtime beginnings and eager anticipation, summer’s sunny stretch and quick growth, autumn’s warm tones that become lasting memories, and winter’s quiet reflection with long, dark nights. Laughter runs through it all, keeping the pace brisk and light. Presented by the Optimist Club of Sheboygan and sponsored by Bank First. Reserved seating is available. Doors open one hour before the show. Tickets are tiered, with Tier 1 at $60 plus fees, Tier 2 at $55 plus fees, Tier 3 at $45 plus fees, and Tier 4 at $35 plus fees. All sales are final with no refunds, exchanges, or weather cancellations. This event is not affiliated with secondary ticket markets, and the Weill Center uses TicketSearch.

M&T's Gibbsville Orchard hosts a mix of seasonal activities and live entertainment. THE STEWED TOMATOES take the stage for their first appearance at the orchard, performing an acoustic blend of country, pop, rock, and blues with their own twist. Enjoy food and beverages, mini 18-hole golf, outdoor games, and apple picking. Please note the rules of no pets and no carry-ins. There is no cover charge.

Queer Fam Game Night at Paradigm Coffee and Music welcomes LGBTQ+ community members and allies for a relaxed, free evening of games. Multiple tables will be available so everyone can choose which games to join. Participants may bring their own favorites or pick from the many provided. To keep the shared games clean, please skip snacks that leave orange fingerprints. This gathering is part of the 2026 Queer Fam Game Nights series.

At Horace Mann Soccer Fields, the Shipbuilders face Sheboygan North in WIAA FRCC play. The schedule features a JV1 game to open the action, followed by the varsity match.

Karaoke at Hika Bay Tavern comes with a twist, adding music trivia to the mix. While enjoying the entertainment, guests can take advantage of the tavern’s daily specials and pizza.

Flora Fields is set to host an upcoming live music performance. More information will be shared as it becomes available.

A friendly poetry club session begins with a brief icebreaker, moves into a short prompt to spark ideas, and wraps up with an optional share-out of fresh writing. Participants can write, listen, or simply enjoy the creative atmosphere. No prior experience is required. All ages are welcome.

The Cheese Doodles bring a lively, family-friendly set to M&T's Gibbsville Orchard. Enjoy a broad mix of songs while you pick apples, smash pumpkins, take a pony ride, or savor food and beverages under the pavilion. This energetic duo spans many styles with plenty of style, and they welcome requests if there is a tune you are ready to dance to. Please note the policies, no pets and no carry-ins, and there is no cover charge.

Gather for a relaxed, low-pressure art critique where conversation is the focus and everyone has a voice. Participants can bring a piece to share or take part by looking closely and offering thoughtful feedback to others. Discussion will explore composition, concept, technique, and intent with an approach that is honest, curious, and respectful. The aim goes beyond receiving notes, encouraging a sharper eye, a stronger voice, and a sense of community. Works in progress and finished pieces are equally welcome, and every perspective matters. Bring your work, bring your ideas, and speak up, because your insight could be exactly what someone else needs.

Entertainer, producer, and steel guitarist Mark Wayne performs a mix of gospel and country, drawing on the styles of Randy Travis, Johnny Cash, Ricky Skaggs, and more. The day also offers apple picking, rides on a tractor wagon, a petting zoo, and a fall-focused gift shop with apple pies, apple cider, and more. Pets are not permitted and carry-ins are not allowed.

At Brick and Mortar Hemp Company, enjoy a calm tea and tarot gathering that pairs welcoming readings with soothing sips. Guest reader Phoenix leads the tarot sessions, and the atmosphere is relaxed and drop-in friendly, suitable for attending on your own or with a friend. With the season shifting, it offers a gentle moment to slow down, reflect, and explore what the cards might suggest. Teas will be available, with the provider to be announced. This event is part of an ongoing series, and details may change or be rescheduled.

Junior's Eats FoodTruck returns for a day of great food, live music, and seasonal fun. Enjoy apple picking and the search for the perfect pumpkin for Halloween. Families can take part in outdoor games, tractor wagon rides, a bounce house, and more. Please no carry ins.

Live music will be featured at Flora Fields. More details will be shared soon.

Explore collage inspired by the forest floor in a hands-on class focused on creating artwork from and about nature. Work with hand-dyed papers and fabrics, silk stripping, cheesecloth, and other materials, then finish your pieces with simple embroidery stitches. All materials are included.

At LushLOUNGE, this hands-on chunky knit blanket workshop pairs crafting with delicious drinks and food. It is great for beginners and experienced knitters alike, and the project is completed using only your hands. Everyone leaves with a cozy finished blanket tucked into a blanket bag and a new skill, plus emailed instructions and yarn buying tips for future projects. The blanket begins as a lap size and often grows to full-body coverage depending on your preferred style. Choose a looser or tighter knit, so sizes vary; the tightest knit is about 45 by 42 inches and most blankets end up larger. Pre-registration is required and seats are limited on a first come, first served basis, with 18 spots available. Two pricing options are offered. The $65 option lets you select from the yarn colors brought to the workshop. The $85 option allows you to preselect one or two colors in a premium, softer, thicker yarn that helps hide imperfections, with color selection handled by email about four weeks beforehand. Registration for the $85 option closes four weeks prior if not sold out, and the $65 option closes two weeks prior if not sold out. Ages 12 and up can work on a blanket independently. An optional $35 add-on is available if you want the experience without the knitting, and your blanket will be completed and ready for you at the workshop. This add-on must be paired with an $85 workshop registration and should be purchased at least two weeks in advance. For last-minute changes due to illness or other conflicts, contact the organizer as soon as possible.

This event presents musicians performing live, offering an in-the-moment listening experience.

Sip&Story LLC hosts a release party for the sixth ACOTAR book, bringing fans together for an evening devoted to Prythian. Themed beverages will be available for purchase, and snacks will be on hand. Admission is free. Costumes are encouraged, whether that means channeling a favorite character or court or drawing inspiration from the series. Wings, crowns, elegant gowns, and leathers are all welcome.

Long after curtain call, this nearly century-old theater is said to stay lively with flickering lights and phantom footsteps. A 90-minute guided experience blends local stage lore with eerie accounts as guests explore backstage passageways seldom open to the public, step into a balcony reputed to be haunted, and stand on the stage lit only by the ghost light. Hear stories of past performers and unusual happenings, and perhaps catch a glimpse of the venue’s most talked-about spirits. Cameras are welcome, since surprises sometimes appear in photos. A cash bar will be available, and beverages may be enjoyed during the tour. Doors open 30 minutes before the experience begins, and there is a brief intermission. This outing suits history fans, theater enthusiasts, paranormal investigators, and the simply curious, though it may not be ideal for children. Some areas are not ADA accessible, and accessibility arrangements can be coordinated in advance. Registration is required at least 24 hours ahead. Tickets are 20 dollars per person plus fees, and paranormal investigation tools are permitted. Bring your curiosity, because the spirits are said to be waiting.

An almost-monthly open mic night at Paradigm Coffee and Music welcomes musicians and poets for short sets. Sign-up happens before the show, followed by performances. The stage is backlined with a bass amp and a guitar amp, and sets are capped at two songs. Poets have a shorter slot, and stand-up is not part of the program. No soapboxing... and please do not inspire more rules.

Craft a piece that glows under blacklight at MAS Arts Studio in a friendly, beginner-focused pottery class. Follow step-by-step guidance to shape your own statement bowl, unforgettable mug, or one-of-a-kind planter, then finish it with glazing before it is kiln fired. Registration includes clay, all necessary tools, instruction, glazing, and firing. Bring your creativity and leave with a handmade work you will be proud to display.

Cinderella takes the stage in a ballet presented by Classical Arts Entertainment and performed by the United European Ballet Company, weaving romance, wonder, and classic storytelling into a richly crafted production. Set to Sergei Prokofiev’s renowned score, the tale follows a kind young woman through hardship and hope, from life with a harsh stepfamily to the splendor of a royal celebration and the fateful fitting of a glass slipper. An international ensemble from across Europe, including leading Ukrainian artists, brings the story to life with expressive choreography and vivid character work. Hand-painted scenery, elegant costumes by European designers, and a filmic atmosphere that blends classical ballet with Broadway-style narrative touches create moments of humor, tenderness, and sweeping ensemble dance. The performance is suitable for ages 3 and up, appealing to newcomers and dedicated ballet lovers alike. Reserved seating is available with five price levels at $90, $80, $70, $60, and $50, plus fees. Doors open one hour before the performance. All sales are final with no refunds, exchanges, or weather-related cancellations. Tickets are handled through TicketSearch utilized by the Weill Center, and secondary ticket marketplaces are not affiliated.

A morning meetup dedicated entirely to networking for real estate investors and business professionals is now taking place in Sheboygan, presented as Wisconsin’s largest real estate investor networking event. There are no pitches, no formal agenda, and no sponsors, so the focus stays on conversations and connections. Attendees include business owners, real estate investors, entrepreneurs, and other high performers who value growth through collaboration. Come with an open mind and be ready to share what you are working on, the strengths you bring, and where you could use help in your business. Free parking is available behind the building, and the group gathers in the bar area between Field to Fork and Il Ritrovo, which are connected. This meetup is held in Sheboygan on the first Thursday morning of each month. Additional monthly gatherings also take place in other Wisconsin cities such as Green Bay, Appleton, and Milwaukee. Updates and ongoing connections are available in the Caffeine & Cashflow Business Networking Facebook group.

This annual vendor fair gathers a wide mix of local sellers in one spot, featuring homemade treats, handcrafted treasures, and distinctive sewn, carved, crocheted, and 3D printed creations. Visitors can explore favorites such as essential oils, spice blends, home décor, gifts, and more. It is a convenient stop for holiday shopping, finding one-of-a-kind presents, or simply enjoying a fun day out in a festive atmosphere. Additional details will be shared as they become available.

Create a serene winter watercolor with instructor Cindy Sarkady in an easygoing, friendly class. You will explore transparent washes, smooth gradients, lifting techniques, and subtle detailing to capture snowfall and a calm seasonal atmosphere. It is designed for beginners and practicing artists who want to experiment with cool palettes and luminous light. All supplies are included, and you may bring your own brushes and paints if you prefer. Please bring a couple of reference photos to paint, with additional images provided. Cost is $45.

Hosted by Tamarisk at the Main Lodge of YMCA Camp Y-Koda, Festival of the Trees centers on holiday cheer and community support. This Christmas fundraiser benefits an individual in need or a local nonprofit through a silent auction featuring beautifully decorated trees, wreaths, centerpieces, nativities, and snow globes donated by local individuals, businesses, and organizations, all showcased in Holiday Haven Hall. Local musicians share Christmas favorites as attendees browse a marketplace of goods from local artisans. An illuminated walk through the woods adds to the festivities, and the eatery offers warm festive cocoa or grog along with something to eat. Sweet treats are available to take home, bringing together the sights and sounds of a nostalgic holiday season.

The Sheboygan South High Booster Club hosts a craft and vendor fair at Sheboygan South High School featuring a wide variety of local craft and small business vendors. Browse unique holiday gifts and decor, enter raffles, and enjoy concessions available all day. Admission is $2. It offers a festive shopping atmosphere with plenty of opportunities to kick off Christmas gifting and celebrate community spirit.

Settle into LushLOUNGE for a hands-on chunky blanket workshop that pairs cozy crafting with delicious drinks and food. No needles are needed, only your hands, so both first-timers and experienced makers can take part. Create a lap-size piece that often grows into a full-body blanket by choosing a looser or tighter style. The tightest weave is about 45 by 42 inches, and many blankets turn out larger. Everyone leaves with a finished blanket tucked in a blanket bag, plus emailed instructions and yarn-buying tips for future projects. Advance registration is required and seating is limited on a first come, first served basis, with 18 spots available. Ages 12 and up can work on a blanket independently. Two pricing options are available. The $65 option lets participants choose from yarn colors brought to the workshop. The $85 option includes advance color selection in a premium yarn that is softer and thicker, offers many color choices, and can help hide small imperfections; an email is sent about four weeks before the workshop to choose one or two colors. If not sold out, the $85 registration closes four weeks before the workshop and the $65 registration closes two weeks before. For anyone who wants the social experience without the knitting, an optional $35 add-on ensures your blanket is completed and ready at the workshop. Purchase this at least two weeks prior. The add-on is available only with an $85 workshop registration. For last-minute changes such as illness or schedule conflicts, contact the organizer as soon as possible to discuss options.

The event is held at the American Club in Kohler, Wisconsin.

Promoted as Wisconsin’s largest real estate investor networking gathering, this Sheboygan meetup is entirely about conversation and connections. The format is simple, with no pitches, no set agenda, and no sponsors, so the time is 100 percent focused on networking. Attendees typically include business owners, real estate investors, entrepreneurs, and other high performers who value growth through collaboration. Plan to arrive with an open mind and be ready to share what you are working on, what you do best, and something you could use help with in your business. Free parking is available in the back, and the group meets between Field to Fork and Il Ritrovo in the bar area, the buildings are connected. This gathering takes place in Sheboygan on the first Thursday morning of each month, with additional monthly meetups held in other Wisconsin cities such as Green Bay, Appleton, and Milwaukee. For updates and connections between events, look for the Caffeine & Cashflow Business Networking group on Facebook.

Blue Harbor Resort transforms into a festive setting for the Run Santa Run 5K, a spirited celebration where holiday characters take center stage. Runners and walkers fill the streets of Sheboygan in Santa and Elf outfits and other wintry looks, spreading cheer with every step. Along the route, participants encounter playful aid stations, a visit from Santa Claus, and a lighthearted mission to keep the Grinch from spoiling the fun. Participants can choose to run or walk as Santa, Elf, or Penguin, with character shirts, hats, or accessories available to help complete the look. The experience is designed for all ages and mixes friendly competition with plenty of seasonal joy. After crossing the finish line, the festivities continue with a North Pole themed post race party at Blue Harbor Resort.