Guy's Weekend Trip to Sheboygan

A couple of months ago, I put together a blog with suggestions for having a girl’s weekend trip to Sheboygan; including suggestions for where to go out for food and drinks, shops to visit, activities to do as a group, and other local gems to enjoy.

I decided it’s time for suggestions for a guy’s weekend. I consulted with my partner on some of his favorite attractions in Sheboygan that he thinks would make for the perfect guys trip in Sheboygan.

Without further ado, let’s get into it!

3 Sheeps Brewery

Who doesn’t love starting the weekend by relaxing with casual company and a drink? After a day of travel, an obvious place to loosen up and kick off the weekend in Sheboygan is 3 Sheeps Brewery. The casual atmosphere, live music, lengthy list of beers to try, and more than enough seating to go around all accumulates as the ideal destination for the guys to gather and start the weekend. Take your time taste testing different beers, ordering beer flights, or trying the Cloudless gluten-free seltzers brewed by 3 Sheeps. Check their schedule ahead of time, but during the summer there is often live music on Fridays playing a range of genres from country, folk, rock, and more. Ultimately, if you’re looking for a chill place to meet up and ease into the weekend, 3 Sheeps is the place to go! The brewery also offers tours every Saturday, so you and the guys can be led around behind the scenes of 3 Sheeps and see the production process of their brews. Tours begin at 1pm each Saturday and last 45 minutes, including an entertaining and informative glimpse into their process, samples of the beers, and a commemorative souvenir glass. You can easily add this tour into your Saturday plans, and chill at the brewery after the tour is over trying more of the beers you just got to see produced.

Outdoor Activities

Depending on your groups’ interests, there are several outdoor activities that will get you out on the water and enjoying Sheboygan’s location on Lake Michigan and the rivers that feed into the lake. If you and the boys enjoy fishing, get out on the water with Dumper Dan’s Sportfishing Charters. Located just across the street from Blue Harbor Resort on South Pier Drive, Dumper Dan’s rests on the Sheboygan River and is close to the mouth of the river where it connects to the Great Lake. Enjoy fishing for Trout and Salmon aboard Baha Cruisers Sportfishing boats, and the feeling of being out on the water. There’s no better way to spend time in Sheboygan than out on the water. If fishing isn’t your groups’ interest, try going on a SEAS (Sailing Education Association of Sheboygan) excursion for a sailing trip on the great lake. Boating is a favorite activity among both the locals, and the tourists in Sheboygan, and there is no shortage of charter boats that can take you out on a spin on the lake, enjoying the wind in your hair, the lake water spraying on your skin, and endless blue stretching beyond the horizon.

Although Sportsfishing and boating is a popular Sheboygan activity, so is paddle boarding, kayaking, and of course, surfing. EOS Surf is a shop and outfitter based out of downtown Sheboygan, who can take groups out onto the lake guiding and teach those new to surfing. Whether your whole group is experienced with these water sports or not, you all will be able to safely participle in these unique Sheboygan pursuits. The Wandering Kayaker is an outfitter who can take groups of 6 on kayaking tours on the Sheboygan river, no matter how much or little experience your group has. Take a paddle up the Sheboygan river enjoying the nature and scenery of the boardwalk businesses, and keep an eye out for wildlife! Whether you kayak, surf, or go boating, you’ll have a day of adventure and enjoying some of Sheboygan’s finest qualities from the water that surrounds the city of Sheboygan.

BBQ, Brats, and Burgers

After your day of outdoor activities, the group will definitely be hungry and ready to eat. Sheboygan is un-paralleled when it comes to brats- after all, Sheboygan is known for its brats. Luckily, there’s no shortage of brats, BBQ, burgers, and sandwiches. Head just about anywhere in Sheboygan and you’ll find the famous brat and hard roll combo, but if you’re looking for some serious BBQ, Parker John’s and Legend Larry’s are both casual places to gather and eat as much BBQ, brisket, and wings as you can. Check the schedule on Parker John’s website to see if they will have any live music while you and your group are in town, and if there’s a game you all want to watch, Legend Larry’s has large flat screen TV’s on every wall. Legend Larry’s menu allows you to choose what kinds of wings you want, let’s you mix and match sauces, appetizers, and of course has a bar with endless options. Parker John’s portions are HUGE, and their Bloody Mary’s are next level: I’m talking loaded with toppings including the typical fixings, and going as far as daunting burgers, wings, pulled pork sliders, bacon strips, and more. These Bloody Mary’s are beyond drinks- they are the star of the show themselves. It’s certainly not for the faint of heart- neither are the spicy BBQ sauces from Legend Larry’s.

Night Life

If you all still feel up to going out on the town after BBQ, wings, and Bloody Mary’s, I have two suggestions of where to go. The first is Shebikin’, a pedal powered city crawler that can seat up to 15 people. You and your group can pedal through downtown, by the river and the lake, hitting local pubs and restaurants along the way. Shebikin’ is a BYOB gig, the only restrictions being 36 ounces per person, and no glass or hard liquor. Start your night out by biking, drinking, and goofing around, stopping at bars in the downtown area as you please. The latest time slot available during the summer is 8:00pm, perfect for getting the night started while it’s still young! Take note that although Shebikin’ can take groups up to 15, there is a 6-person minimum requirement. After your Shebikin’ experience is over, I suggest heading to Hops Haven off of N 14^th St. This is bar is a chill hangout spot serving beer, cocktails, and wine, as well as bar food. AND they have plenty of bar games, including pool, shuffleboard, darts, pull tabs, and more. I have no doubt the boys will have no problem hanging around until bar close, Hops has it all!

Sheboygan is a versatile destination for your group of friends to take a weekend getaway trip, your group is sure to have a great time making memories, trying new restaurants, hanging out on the water, and keeping quality conversation over drinks.