Fall weather in Chicago can be a bit of a gamble. You could get a gorgeous, sunny 65-degree day or you could be freezing your butt off in a winter coat. There’s really no telling.
Thankfully, we lucked out BIG TIME for this family session at Tower Road Beach in Winnetka. Not a cloud in sight, but just cool enough for sweaters. My idea of heaven, really.
I met the S family at Tower Road Beach for their session, and we kicked things off at the top of the bluff so their dog Henry could join us for a few photos. Because obviously, the four-legged family members deserve their moment, too.
After Henry’s modeling debut, we headed down the approximately one million stairs to the beach. (Okay, slight exaggeration. But if you’ve been there, you know.)
Family Photos at Tower Road Beach in Winnetka
A little heads-up if you’re considering Tower Road Beach for your own family photos and aren’t familiar with the location: there’s a playground right by the beach. And when I say right by the beach, I mean you basically have to walk past it to get to the water (and it’s a small beach).
Which, depending on your kids, could go one of two ways.
For some little ones, knowing there’s a playground waiting for them after photos is the ultimate motivation. For others, being asked to smile for pictures while a perfectly good playground is RIGHT THERE might be a tough sell.
Neither is wrong. Just something worth keeping in mind when choosing a location, especially if you have toddlers who are still working on that whole delayed gratification thing. (Honestly, same.)
A Little Lake Michigan Magic
Playground distractions aside, I absolutely love photographing families by the water. There’s just something about Lake Michigan that makes my heart happy. The open sky, the sandy beach, the gorgeous light. It’s one of my favorite backdrops for family photos on Chicago’s North Shore.
And this particular session was extra sweet because I got to meet the S family’s newest addition, Josephine!
At just three months old, she was already absolutely crushing it as a baby model. A natural, obviously.
And big sister Madeline? I mean, COME ON. The cutest thing ever. Also, can we please talk about those striped pants? I would like to know if they come in adult sizes because I would absolutely wear them.
Between the beautiful weather, the sweetest kiddos, and a little Lake Michigan magic, this session was such a good reminder of why I love what I do.
Looking for a North Shore Family Photographer?
If you’re thinking about family photos in Winnetka or anywhere along Chicago’s North Shore, Tower Road Beach is such a beautiful option, especially in the fall when you can get those perfect sweater-weather days.
I’d love to help you plan a session that feels relaxed, fun, and true to your family. Playground negotiations and all.
Learn more about my family photography sessions here.



























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