mother and son fall family pictures

Wisconsin Fall Family Weekend Getaway Photo Diary

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

I’m lucky that we’re a family that all likes to travel. My 1-year-old will frequently hand me his shoes because he wants to leave the house and my 4-year-old will ask me when we’re going to go somewhere because he’s “never been anywhere before” haha. (He really means “today” and we’re working on the right language to express time.)

Thankfully, my kiddos are pretty flexible with their routine, so if we have the opportunity to go somewhere to spend some family time we’re going to take it. We’ve been embracing the idea of a staycation (or not traveling very far) lately.

Living in a cramped rental in the middle of everything including a busy college has us craving peace and quiet whenever we can get it. And when you feel pretty tapped out, the thought of getting everyone on a plane (even for a sunny getaway) sounds so not worth it.

Instead, recently we took advantage of a free weekend and booked a stay at a woodsy cabin nearby. I’m thankful that we get these opportunities to reset, admire God’s creation, and have space to let our boys run wild!

Our Airbnb greeted us with a long private driveway.

After getting settled in, I explored the property with my camera. My love for photography started out with capturing nature and I know my heart will always find a feeling of peace in doing just that.

The property included a lake. Too cold to swim, but just right for looking at!

Progress on our custom build is slow and that can be discouraging at times. But all I have to do is remind myself that one day I’ll get to walk around the woods capturing pictures of nature, except it will be on my land and I won’t have to “escape” to get it. That’s when the gratitude sinks in.

Mmm, you can almost smell that bacon. Getaways are even better when I don’t have to make breakfast!

Captured: Father and son having a cozy moment by the fire.

In the slow afternoon, we made up our own version of Candy Land.

playing board games at a cabin

As we waited for our bonfire to start blazing, we took a family walk around the property.

And of course, I had to take some pictures with my boys. Who remembers when Will was born? Can you believe how old he looks now?

Being a boy mom is all kinds of special.

Once they got tired of taking pictures, we had dinner by the fire. Macaroni as requested!

toddler boy fall pictures

A weekend never seems like enough time, especially when you don’t want the time to end.

I forgot my tripod and I didn’t coordinate outfits (though it actually looks pretty decent), but I managed to snap a family photo. Whether it’s “picture perfect” or not, I’ve never regretted capturing these moments.

family fall picture

My boys.

Our last family trip was to Mexico and we’re hoping our next big family trip will be to the South of France next year. But I’m learning that not everything needs to be big. Some of the best trips are the small ones.

Up Next: How To Tackle Big Sur As a Family Vacation


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.