A Halloween-Fanatic’s Guide to Top 5 Spooky Events in Sheboygan

If there is one thing I go absolutely all out for, it’s Halloween. Ask me any random day of the year how many days it is until Halloween, I won’t hesitate. And as much as I love the holiday, I love the month it resides in. October has got to be one of the best months, period. I know a lot of people agree especially here in the Midwest, October is when we get the gorgeous transition weather. It’s the perfect in-between temperature; August’s blaze has died out, the air is crisp and comfortable for layering, but it’s not so cold that you need to bundle up in your winter scarves and jackets. Plus, the changing leaves are at their peak throughout the month of October, as is football and tailgating season, pumpkin flavors, and moody skies. If you’re psycho for Halloween like I am, it’s also the best season for horror movie marathons, haunted houses, and skeleton-decorated everything.

So, naturally, being new to Sheboygan (in addition to being the self-proclaimed Queen of Halloween), I have to learn about all the spooktacular attractions and things to do that are related to the most wonderful time of the year: O C T O B E R.

1) BOO-Harbor

Okay, give me a break. It’s my favorite holiday of the whole year- and the place I work- so two of my favorite things in my life. But trust me, this event would be at the top of my Sheboygan list of Halloween-related activities whether I worked at Blue Harbor or not. Fellow Halloween connoisseurs and families looking to get festive, you won’t want to miss this.

Blue Harbor cleverly hosts their play-on-words Halloween event, BOO-Harbor, almost every year. This event is ideal October fun for families, couples, team building, and everything in between. There are festivities for people of all ages to enjoy, whether you are bringing trick-or-treaters with you, or looking for an adult treat… (a.k.a. spirits)

A large reason why I love Halloween so much still as a 22-year-old young adult has to do with the Halloween memories I have from when I was a kid. I loved dressing up and getting candy as much as the next kid, but what really sold me on the holiday was all the fun spooky activates. Decorating the front yard with purple and orange lights, fake spider webs, and giant pumpkins, carving jack-o-lanterns or painting scary faces on pumpkins, baking special treats shaped like ghosts and gravestones, or watching Halloween specials in the evening with the glow of the plug in pumpkins on either side of the TV. Plus, I was a kid into all things creepy. I even had a picture book titled “Animals Nobody Loves” full of pictures of spiders, reptiles, and nocturnal critters. Sorry mom.

So an event like BOO-Harbor is exactly the type of event that little Em would have DREAMED of. The opportunity to dress up in my Halloween costume and showing it off in a costume contest, trick-or-treating, decorating pumpkins and cookies, coloring pages of Halloween-themed pictures, and running around a massive hotel decorated for the occasion, it would have been my own personal heaven. There are so many fun activities for kids to indulge in at BOO-Harbor allowing kids to be creative, excited, and enjoy this holiday in a not-too-spooky way.

There are also events for adults and parents to enjoy at BOO-Harbor- and they are sure to get you in the spooky-mood. For those who enjoy cocktail parties, and Bloody Mary’s in particular, Blue Harbor offers a Bloody Mary and Buffet special on the weekends of BOO-Harbor. Leave the mixing to our bartenders, and garnish your Bloody Mary so that it’s perfectly tailored to you. Additionally, in the evening you can enjoy your Bloody Mary at a Witches Brew Bonfire out on our back lawn. Adults, you can get as festive as you want, dress up in the Halloween spirit- or not. It’s a custom Halloween experience for families, groups, and couples!

2) BOO-tique Crawl

What’s better than Halloween and shopping combined? Maybe Halloween Shopping, but besides that, this combination is calling my name. Luckily, there is an event just for people who share this niche interest with me! The annual BOO-tique crawl takes place on October 9^th Downtown on Riverfront and South Pier, with participating businesses offering special deals and promotions during the crawl. On top of these specials, by participating in the BOO-Crawl and supporting small local businesses, shoppers will be entered to win prizes for local restaurants and shops. I love window shopping during the “ber” months for several reasons. The first being that by October- I like many others- I am already on the lookout for unique gifts for the upcoming holidays, and strolling through different local businesses makes it easier to find a unique and meaningful gift for friends and family. Another reason I enjoy window shopping this time of year is because it’s fun to walk around and enjoy the festivities that we start seeing more businesses partake in during October. The decorations, seasonal products, and cozy vibe that local businesses have as the days get shorter is practically contagious. I just want to enjoy it all, the scents, the flavors, the colors. Plus, I certainly want to see the collection of Halloween related products.

3) Happily Haunted Bookworm Gardens

Bookworm Gardens in Sheboygan is a magical place to visit in the Summer and Autumn; their gardens have the ability to transport your imagination to places both new and nostalgic no matter your age. The garden is, of course, mainly a summer attraction here in Wisconsin, but Bookworm Gardens does stay open through the Fall. One reason for that is their spectacular Halloween lights display, Happily Haunted. Enjoy walking through the magical garden while thousands of twinkling lights guide your way through this friendly and not-so-spooky attraction. It’s the perfect festive activity to attend if you have little ones or if you just prefer the milder side of Halloween. In addition to all the wondrous lights that are strung up, Bookworm Gardens also offers a scavenger hunt, stories, and a pumpkin walk for the kiddos! Costumes are more than just welcomed, they are encouraged! There’s no need to bring any trick-or-treat bags because all kids take home a little treat bag. Additionally, there are snacks, festive beverages, and a dinner fare all available for purchase should you choose. All in all, it’s an excellent event no matter how much you like the spooky side of Halloween. One aspect of the Happily Haunted event that I am all about is the pumpkin walk. Kids, adults, and anyone in between is invited to decorate a pumpkin of their own -whether that’s painting, gluing, bedazzling, you name it- and drop it off at the gardens between October 8^th and 11^th and your pumpkin will be on display during Happily Haunted. As an artist myself, not to mention an avid pumpkin decorator this time of year, I can’t wait to plan out my pumpkin, paint it, and know kids and adults will get to see and enjoy it during this fun event.

 4) Dominion of Terror

This local Haunted House attraction is my kind of terror; a non-profit haunted house that is focused on giving back to the community, “one scare at a time.” Located in Sheboygan near 3 Sheeps Brewery, this 20+ room haunted house is worked on year-round and run by volunteers. The weekend of October 13^th and 14^th, the Dominion of Terror holds “throwback weekend.” Normally, admission is $20, but for that weekend, the haunted house offers tickets for $15 like they did when they first opened nearly 50 years ago. This haunted attraction is an annual favorite in Sheboygan that has stood the test of time, and with good reason. The property Dominion of Terror resides on property owned by RCS, a non-profit whose mission is to empower and advocate for individuals with disabilities and special needs. Not only is this an important cause, but it’s one that is very close and personal to me. I was super excited to check out Dominion of Terror this past weekend and engage in two things that are central aspects to my life: supporting a non-profit and enjoying a night of horror. Let me tell you, I was not let down. This haunted attraction was amazing, a perfect length, countless rooms decked out with creepy, disorienting, and chilling horror scenes. The Haunters were excellent too, their characters detailed, dedicated, and fun. There’s a particular clown at Dominion of Terror that is a bit of a mascot for them who carries a sign announcing “free hugs” and to say the least is VERY charismatic! I was surprised and impressed by how much this non-profit and volunteer-run haunted attraction had, it is truly outstanding. You can tell that everyone who has a hand in putting on this production year after year for the past several decades truly have a passion for Halloween and helping those in need. For these reasons alone this event should be on your list of Halloween Fun to do in Sheboygan, but especially if you like trying to spook yourself like I do.

5) Wisconsin Fear Fest

This is yet another haunted attraction in the Sheboygan area, and it’s just opening its doors for the 2023 season by the time this blog is published! Because of that, I haven’t been able to attend this event YET but you bet it’s on my list. Three haunted houses, a haunted hay ride, a rage room, escape rooms, it’s the Halloween HUB for fear. Fear Fest is not for the faint of heart so consider this your warning to either skip out on this event if it’s not your forte, or to add it to the top of your list if you like being scared! Perhaps this blogger will return with another Halloween related blog after she has the opportunity to attend this event…

Stay Tuned!

Once again, because it bears repeating, I am CRAZY about Halloween, so although this brings us to the end of this particular blog on spooky Sheboygan experiences it doesn’t mean I won’t find more creepy-cool fun to indulge in and share with my readers. But for now, you know the drill- rock on Sheboygan and stay spooky!