Midweek Meetups and Small-Town Gems: A Day Trip to Sheboygan, Wisconsin
Tuesdays have become kind of sacred for my best friend Paige and me. We both have the day off, so we try to make the most of it. Lately, that’s meant paddleboarding—we both love being out on the lake, getting a bit of a workout in, and getting in a fun little swim. But this week, Paige’s board had a small leak, so we decided to switch things up while she gets it patched.We live about two hours apart, so we try to meet somewhere in the middle. Sheboygan is kind of a perfect half-way meeting point. It’s got that relaxed small-town feel, but there’s enough to do that we can turn a simple day off into something that feels memorable.
Coffee at the Greenhouse at Kohler Resort
We started the day at The Greenhouse at Kohler Resort, which had a little moment on TikTok a while back. I’d been once before in the winter—it was beautiful but freezing inside. This time, with the sun out and the windows glowing, it felt much more inviting.
I got a banana and dark chocolate decaf iced latte with almond milk, and Paige went with a London Fog latte. Both were solid—definitely a step up from my last visit. They’ve started making a few of their own syrups in-house, which is always a nice touch.
After coffee, we walked around the gardens tucked into the resort grounds. It’s one of those places you wouldn’t expect to find unless someone told you about it—quiet, a little tucked away, and really peaceful.
Thrifting for Fall and a Closet Refresh
Next up: thrifting. I was hoping to find a few more workout tops and some sweaters for layering—Scotland in December demands warmth and layers to combat the weather. Paige was on a mission to finally retire her collection of skinny jeans and try something with a looser fit.
We each grabbed carts and split up, then met in the dressing rooms like we always do. Paige hit the jackpot with jeans—I think five pairs worked out. I found five sweaters I’m excited about, a really nice worn-in leather belt, and two decent workout tops. We didn’t get everything we were looking for, but not a bad haul either.
Dinner Plans Don’t Always Go to Plan
We decided last minute to go back to Black Pig, a restaurant we’d eaten at a twice before. But when we looked at the menu, it had gotten a lot more expensive, and the gluten-free options were limited. So we pivoted and found a spot nearby called Cocina Mi Familia.
The place was super cute, friendly, and had a nice patio. Their homemade salsa was the standout—it had that fresh, bright flavor that doesn’t need anything fancy to make it good. I got al pastor tacos, she got fajitas, and we both got a margarita. It ended up being the perfect casual dinner.
Wrapping Up a Low-Key, High-Quality Day
We had one more thrift store on our list, but it had already closed by the time we finished dinner. Not a big deal—by that point, we were ready to head home.It was one of those easy, low-pressure days that feels restorative. A good mix of catching up, being outside, and doing something productive (if you count adding to your fall wardrobe as productive, which I do).
Looking Ahead
We actually get to see each other for a second time later this week, which is rare. We’re heading out on a boat with one of my late brother’s friends for a lake day, which should be a good time.
These kinds of days always remind me how important it is to make time for your people—especially when life gets busy and routines take over.
The Roaming Rebel 
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