A winter trip to Sheboygan

I have a soft spot for the off-season.

Having lived in resort towns for most of my life, I appreciate a good busy season (and its corresponding tourism) for what it provides businesses and communities. But I also love the quiet tenacity of a shoulder season. This is when the locals take over and the honest normalcy of a destination is on display.

Chad and I took a quick weekend getaway to Sheboygan, WI. I haven’t heard much about Sheboygan outside of its summertime glory: it’s known as the “Malibu of the Midwest,” with gorgeous white-sand beaches, spas, and small-town charm.

For us, we didn’t get to experience any of that. However, we loved every minute of our snowy, wonderful overnight experience in Sheboygan in off-season December.

The Watershed Hotel

Usually when it comes to travel, Chad and I do a fair amount of research beforehand—activities, breweries, attractions in the area. This time, however, we knew that we were heading to the “Malibu of the Midwest” in the middle of a snowstorm, and maybe because of a little seasonal burnout, we opted to play as we went.

Our first stop after arriving in Sheboygan (which is an easy hour drive north of Milwaukee, by the way) was directly to our hotel, the new Watershed Hotel. Upon check-in, we were met by the most delightful duo: manager Bailey and future service dog Hugo (a golden retriever puppy), who will go to an autistic child once his training is finished. In the meantime, however, he’s getting socialized with belly rubs and kisses at the front desk.

Thanks to Bailey, Chad and I walked away from our check out with a full itinerary of our stay—she offered several wonderful suggestions and we happily took them all. It turned out to be the best decision we could’ve made!

Making Spirits Bright

One of the main events for Chad and I was a drive-through holiday light display called Making Spirits Bright. It’s put on by the Sheboygan Rotary Club and is an incredible feat—it involves half a million colorful lights, put up in dazzling displays set to a radio station playing Christmas classics. It was probably half an hour’s worth of cheer!

It’s free to attend, though donations of canned goods or a few dollars are recommended. It starts late November and goes through New Year’s Eve and is run by volunteers.

Chad and I were blown away by the display and had never experienced anything like it. So impressive! Another huge shout out to Amanda for recommending it to us—it literally made our night. We vowed to return next year as a new tradition!

Eating, drinking, and merriment

Our first food stop was at Luigi’s, where Chad and I enjoyed a family-style Italian meal that really hit the spot. We delighted in a simple fact: you can never go wrong with a cheesy pizza.

Afterward, we went to Three Sheeps Brewing Company, which has been on our list for quite some time. It was awesome! Not only was their entertainment with a high school band’s holiday concert, but the drinks were varied and delicious. We loved the space, the beer, the dog-friendliness, and imagine that the summertime patio can’t be beat.

Relaxing back at the room

Chad and I ended our night with some well-earned rest and relaxation in our room at the Watershed Hotel. We loved it! Not only was it spacious, modern, and clean, but the bed was so comfortable. We popped a movie on the TV and couldn’t get over our wonderful and unexpected evening in Sheboygan.

The next morning, I awoke to an incredible surprise: blue sky! Our room was filled with large windows, but the best view came from the attached balcony. Outside, it felt like a postcard: the Sheboygan River ran right by, framed with snow from the night before and the gorgeous sky above.

I could have easily stayed out on the balcony all day.

Sheboygan’s 8th Street

Before heading back to Milwaukee, Chad and I went down to Sheboygan’s downtown, 8th Street. It’s charming and bustling with small town energy and lots of local businesses.

I imagine it gets busy during tourist season in the summer (fun fact: Sheboygan is known for their surfing!), but for a Saturday morning in December, we found free parking easily and had no wait for breakfast at Field to Fork. We had a delicious meal (I loved their biscuits and gravy), and felt charmed by all the holiday themed decorations throughout the city square.

Though our trip to Sheboygan was brief, we packed in an incredible amount of fun—more than most would expect, during a snowstorm to a summer destination.

If you’re looking to visit Sheboygan, Wisconsin, don’t wait. There’s plenty to do, see, explore, eat, and enjoy, right now.