(Kelsey Dayton is a former Jackson resident who now lives in Lander. She wrote our cover story on the Victor Emporium’s huckleberry milkshake for the summer/fall issue. Thanks to her sweet tooth, we now know where to find cupcakes in Chicago.)
I have always loved cupcakes for a few basic reasons.
I love cake.
I am incredibly indecisive, and with cupcakes, if I can’t decide if I’m in the mood for Red Velvet, or want to try a more creative flavor like chai — well cupcakes are small enough I can get both.
I am easily swayed by visuals, and cupcakes are, at the very least, cute, and at, best exquisite.
My friend, Andrea, is one of the few people with a sweet tooth rivaling my own. In college she introduced me to a grocery store that sold cake by the slice, perfect for anyone who wanted cake just because it was Tuesday, or Thursday or Sunday afternoon. When I visited Andrea in Washington DC several years ago, she greeted me with a surprise: cupcakes from her new favorite bakery Georgetown Cupcakes.
I still remember the first bite of the banana chocolate one I nibbled. The icing was the perfect consistency, light and sweet. The banana was infused not just in the moist chocolate cake but also in the frosting.
That cupcake was a turning point. No longer did grocery stores — or most bakeries — meet my new high cupcake standards. It started an obsession to find equally delicious cupcakes that has spanned the country. Each city I visit usually involves stops and comparisons at cupcake shops.
When Andrea asked me what I wanted to do when I visited her in Chicago over Memorial Day, I half-jokingly suggested a cupcake tour of the many bakeries Andrea spoke about in the city. Soon after, I received an email with a PDF map of Chicago with pink cupcakes marking different stops (find it at the . Our weekend plan was set.
Andrea picked only bakeries that specialize in cupcakes and were in the main part of the city.
We started out ambitiously — one day and seven cupcake shops — but had to split our tour into two days after realizing, even with our high sugar tolerance, the walking between cupcake shops helped us digest and we found ourselves surprisingly full after our first stop and uncomfortably full after the fourth.
The tour, which involved us walking more than six miles the first day, was the perfect way to see Chicago. We stopped in shops or hopped a boat tour as we made our way across the city cupcake-to-cupcake.
For those not headed to Chicago anytime soon, read-on, many of the bakeries deliver nationwide.
Here’s what we found:
Stop No. 1: Phoebe’s Cupcakes
Cost: $2.95 per cupcake
What we got: Pear Melba and Margarita Cheesecake
What we thought: Phoebe’s had the most interesting flavors we’ve seen as far as cupcakes with ones like Mango Chili Pepper. Our cupcakes, which we split, were super moist with a very subtle, almost non-existent flavoring. The icing was melting and a bit runny due to the heat.
Stop No. 2. Molly’s Cupcakes
Cost: $3.75 per filled cupcake
What we got: Peach Cobbler and Peanut Butter Nutella
What we thought: Molly’s is known for cupcakes with filling. The peach cobbler was like eating a peach cobbler. It looked and tasted like the dessert- but not like a cupcake. If we wanted a peach cobbler we would have just gone somewhere and order it. The Peanut Butter Nutella Cupcake was so thick it was like eating a thick peanut butter cookie and tough to get down.
Stop No. 3 Swirlz Cupcakes
What we got: Gluten Free Banana Nutella.
What we thought: It was basically banana bread with icing and a thin layer of nutella, delicious but not necessarily a cupcake.
Stop No. 4: Sweet Mandy B’s
What we got: Snickerdoodle
What we thought: The flavor was in the frosting. We could taste the cream cheese in the frosting, but also cinnamon. The cake itself was fairly non-descript in flavor. The bakery was cute, decorated in sugary pastels with plenty of seating.
Stop No. 5: More
What we got: S’mores
What we thought: The S’mores was so pretty we ordered it despite More being known for its savory cupcakes, specifically bacon maple. This was the richest cupcake we tried. The chocolate cake had a marshmallow filling and the frosting tasted like graham crackers
Stop No. 6: Sugar Bliss
Cost: $1.50 for minis
What we got: Orange creamsicle and banana chocolate minis.
What we thought: “Major points for the minis in all the flavors,” Andrea said. The cupcakes were fully infused with flavor. However the icing was so sweet and sugary it almost made your teeth ache. This was of course, our sixth stop on the tour, so perhaps our bodies were becoming extra sensitive to the mass amounts of sweets we were ingesting. Andrea let me know the bakery does offer frosting shots, but neither of us could stomach the thought of an extra dose of frosting when we still had one more stop.
Stop No. 7: Sprinkles
What we got: Salty Caramel with sea salt and lemon
What we thought: Unintentionally we saved the best for last. While Sprinkles’ cake is very dense and filling, the flavor can be tasted in the cake and frosting. Plus, our favorite thing was the sea salt on top of the Salty Caramel. We finished our tour toasting cold glasses of milk we bought to go along with the last cupcakes either of us would eat- at least for a few days.
Here’s a handy map to print off for your own cupcake tour.