How to Have the Sweetest Day in Kansas City: Your Guide to A 10-Stop Dessert Crawl

A few things we’ve already established:

I love birthdays.

I love to eat.

I love sweets.

You may remember that, back in January, my husband and I celebrated his birthday by visiting nine different BBQ restaurants in one day. And if not, you can read all about it in this post. So it was only fair that when my birthday hit the calendar, we celebrate with the most appropriate version for my personal palate: A Dessert Crawl.

The concept seems pretty straightforward, but it must be said, the planning of this adventure proved much harder than one would expect. In your visions of eating your way through the city, one cookie crumb at a time, here’s something you don’t consider–Dessert is everywhere. Literally everywhere. Every restaurant has a dessert menu. Coffee shops have cookies (and more). There are more bakeries than can be counted. And let’s not even start with the ghost kitchens and hidden menus. The list grows by the second, and it’s enough to overwhelm even the largest sweet tooth. So where to start?

When I sat down to coordinate a game plan, there were several directions I could have taken in my approach. And after several scratched up pieces of paper, I landed on the strategy of Dessert Categories. I started by making a list of Dessert Categories: cupcake, cookie, cake, ice cream, etc. That alone has so many options and variations, but I landed on a solid list of ten core dessert categories.

Once I had my categories, I plugged in my KC favorites (It was MY birthday, after all…), the most recommended by friends, and the most well known or highest regarded. This exercise was similar to picking a favorite child, because I’ve never had a bad dessert in our city, and so many of our hometown heroes offer delicious choices in several categories. But you gotta start somewhere, and there’s only so much your stomach can handle. (To which I say, “Hold my beer!”)

Once I had the categories, and the list of places, I had to create our route. As I’ve mentioned before, I am not the most directionally gifted individual, so I anticipated this would be another challenge. (I promise I actually have fun planning these things, regardless of how many times I use the word “challenge.”) However, the Kansas City Dessert Infrastructure Division (that’s definitely a thing) has done an exceptional job of situating so many places in close proximity, which really helped a girl out.

The categories, the places, the route, done. Let’s go!

Here is a recap of our adventure, and keep scrolling for some ideas and recommendations for a Dessert Crawl of your very own. Because you’re totally doing it. Right? As a reminder: Only order one of each item and share. Otherwise, those final stops might be pretty painful or nonexistent.

Stop 1: Fairway Creamery (Fairway, KS)

What To Get: Donut

Stop 2: Dolce Bakery (Prairie Village, KS)

What To Get: Cake

Stop 3: Andres Confiserie Suisse (KCMO, South Plaza)

What To Get: Chocolate

Stop 4: Heirloom Bakery & Hearth (KCMO, Brookside)

What To Get: Cookie

Stop 5: McLain’s Bakery (KCMO, Brookside)

What To Get: Cupcake

Stop 6: Ashleigh’s Bake Shop (KCMO, Westport)

What To Get: Pie

Stop 7: Bloom Baking Co. (KCMO, River Market)

What To Get: Macaron

Stop 8: Betty Rae’s Ice Cream (KCMO, River Market)

What To Get: Ice Cream

Stop 9: Best Regards Bakery & Cafe (Overland Park, KS)

What To Get: Brownie

Stop 10: Sweet Thang & Cafe (Olathe, KS)

What To Get: Milkshake

I’m really pleased with our plan, and I would definitely recommend this approach. But I have so many other ideas for future versions. (Yes, of course I’m doing this again.) Here are a few:

  • Pick one of the categories, and make that your theme for the crawl. Examples: Cupcake Crawl, Cookie Crawl, Ice Cream Crawl. Eating from one category at multiple spots throughout the city.
  • Kansas City Signatures: This will require a little more research and planning, but it’s high on my radar. Design your adventure around desserts that are KC faves. Examples: McClain’s Cupcookies, Creative Culture Milkshakes, Tannin Fudge Stuffed Peanut Butter Cookies. The best type of sightseeing.
  • Stick to one area of town. Like I said, EVERYONE has dessert. So pick a spot of the city that’s walkable, and make dessert stops along the way. Examples: Country Club Plaza, Brookside, Downtown Overland Park.
  • Group Favorites: Go with a group, and each person in the group picks their favorite dessert place, and you design the crawl around checking off those super sweet boxes.

There are so many possibilities, and I’m really going to enjoy adding to the list and trying them all!


Molly B.

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