School’s Out Chocolate Cupcakes with Whippy Chocolate Frosting

It’s Sunday, so that means Alyssa is sad. There’s always something sad on a Sunday for that child of mine. This week, it wasn’t that she had to wear a dress, but because the big sister would share her bubbles, her ball, her spot on the couch. There were many, many things to be sad about today, but the more horrid of all trickled into her mind well past bedtime. It was nearly ten o’clock when I went into her room for a late night tuck and discovered her weeping.

“Baby, what is wrong?” I begged of her, cradling her tender cheeks with my lips as I spoke.

“I don’t want to go to school anymore! I just want it to be summer!” Whimper. Gasp. Sniff.

It didn’t matter that there are two field trips this week. It didn’t matter that she’s a mere six days from the bliss of summer freedom. All she knew was that she was home and safe and wearing pajamas, and all of that would change at 6 a.m. tomorrow when her alarm clock rings.

I was tempted to tell her she’d be just fine and the week was going to fly by, but remembered the words of Gretchen Rubin in The Happiness Project when she says that acknowledging a person’s feelings can actually help them get over them.

So, rather than saying, “girlfriend, it’s late. You’re tired.” I ran my fingers through her hair and said, “Lyss. I can tell you are so sad to think about going back to school tomorrow.”

“I ammmmmmm!” she wailed.

I’m so sorry, I said.

Then her daddy came and kissed her and offered a tuck and she was asleep before one could say overdramatically exhausted.

But you see, here’s the secret. I feel just the same as that little Alyssa of mine. Bring on the sunshine. Call off the routine. I’m ready for lazy days and lollipops. I want to walk barefoot through the green grass of our backyard and read books at absurd hours of the afternoon. Why do we have to go to school anyway?

Well, thank goodness. In six days, we don’t.

So to celebrate, here is one of my favorite ways to treat a class full of students to an end-of-summer treat. These chocolate cupcakes are sure to win you the title of Room Mother Extraordinaire. Popping  a wee, colorful sucker right inside makes a quick and simple decoration that kids of all ages are sure to adore.

Kids and moms. Cupcakes and the Last Day of School. It’s the simple things, you know.


Whippy Chocolate Frosting


2 sticks butter
1 ½ c. brown sugar
3 eggs
2 squares unsweetened baking chocolate
1/2 Tbsp. olive oil
1 c. milk
½ tsp. baking powder
½ c. cocoa powder
1 c. flour
1 tsp. pure vanilla

1 (8 ounce) package cream cheese, softened
1/2 cup white sugar
1/3 cup cocoa powder
1 teaspoon vanilla extract
2 cups heavy cream


In a large bowl, cream butter, sugar and eggs until extremely fluffy (this step is CRUCIAL. Don’t skip it!). In a small bowl, microwave baking chocolate and olive oil just until melted (about 1 minute), stir, add to batter. Add remaining ingredients and whip until evenly incorporated but DO NOT MIX. Fill cupcake wrappers 2/3 full with batter, then bake in an oven preheated to 350 degrees for 18-20 minutes.

In an electric mixer fitted with the whisk attachment, beat together the cream cheese, sugar, cocoa powder and vanilla. While the mixture is still whipping, slowly pour in the heavy cream. While whipping, turn off your mixer and scrape the bottom of the bowl. Beat until the frosting holds a stiff peak.

Pipe frosting from a pastry bag fitted with a large star tip onto cooled cupcakes.

36 Responses to “School’s Out Chocolate Cupcakes with Whippy Chocolate Frosting”

  1. ashley says:

    All purpose or cake flour? Can you use either?

  2. Elizabeth says:

    These look great! I’m a little confused about the batter though…when do you add the flour, milk, etc? Also, do you think these need to be refrigerated or will the frosting hold up at room temperature? Thanks!

  3. What a fun treat, for kids or adults! I wish I was in the class, they look just delish!

  4. Shauna says:

    Those kids are so lucky they can have homemade treats brought into the classroom!!

  5. Amanda N says:

    Fun! And they make for good, colorful pictures too. I don’t have kids, but I hear a lot of my girlfriends say that their kids’ schools don’t allow homemade food to be shared anymore. Isn’t that sad?

  6. You are the best mom ever!! I totally agree. Sometimes, a kid just needs a sympathetic hug and be allowed to cry it out.

  7. Ashley says:

    Those look soooo fun! And I loved that book. Isn’t it crazy how acknowledging their feelings really does help? Who knew? I mean seriously, who wants to be listened to? :)

  8. Karly says:

    I love that you used a sucker as a way to decorate the cupcakes. Such a cute idea!

    Hope this last week goes quickly for your little ones! We homeschool and I was a baaaaad teacher this year, so we still have another month or so left to go. That’s what I get for taking unplanned vacation days, I guess!

  9. Donna says:

    Love the cupcakes. Going to have to try them with the cream cheese frosting, they look delish!

    Our poor kids having to go to school every day, it’s hard. My youngest one has a hard time going to sleep at night. Who has heard of a 10-yo insomniac? But if I just let him crawl in my bed he usually crashes and we can move him into his when we go to bed. It’s the little things that comfort our children.

  10. Amy Allen says:

    I’m totally making these when my kids get out of school on JUNE 20th!!! What the heck is that? This last month is killer because we feel ready already, you know? And I’m just not one of those moms that dreads them getting out of school or gets excited for them to go back. If I wasn’t such a fanciful, flighty, unscheduled type of person, I would home school them just so I wouldn’t have to be without them. But I am honest with myself and we would spend more time doing nothing/fun things than actually learning.

    But these cupcakes will sure help. What would I do without you and all your fun food?

  11. Katrina says:

    Amazing looking cupcakes!

  12. Amy P. says:

    Looks Yummy!!! My oldest will finish kindergarten in June and I will have to make these for him!! Thanks!!! what a fun way to celebrate a first year of school!!

  13. Becki says:

    Oh that sweet Alyssa, she is such a dear. Hang on- summer will be here before you know it!!!!! The treats look delicious Brooke! Thanks again for being so talented!

  14. suzanne singer says:

    I wanted to make cupcakes for my daughter’s class and these look great. She is also a bit of a drama-mama and I have to just hug her and listen.

  15. Anna says:

    aw, an adorable story. i feel just the same on sunday nights! can’t wait for summer!

  16. Lindsay says:

    All your Cupcakes are lovely and always look soo good. I believe this is my new go-to chocolate Cupcake recipe. I normally use your other Chocolate recipe but this one sounds good just by reading the recipe. Thank you! :)

  17. Jamica WIlcox says:

    AMEN!!! Bring on those summer days! And bring on last minute trips to Rock Ledge Ranch, or a new park! We hope our paths can cross more these next few months! Mwaa!

  18. awww… I think we all felt like that at some stage during our school days! Chocolate cupcakes make the world a little brighter!

  19. becca says:

    hi brooke! i’ve been a fan for quite a while now, but this is my first time posting. first of all, all of your recipes look amazing. i have yet to make any, because i’m pumping myself up first :)

    i had a question… when you said “whip” but “do not mix,” what do you mean?

    you should totally have videos on step-by-step instructions for little things. considering the quality of your food and photos, the videos would be an excellent addition to your website. “how to frost cupcakes.” “how to whip frosting.” “how to embellish a lovely plate.” etc.

    • Brooke says:

      Becca- I WISH I could have such videos. Brilliant! I’ll put it in my list of to-do’s and try to make it happen someday soon.

      When it says “whip” but do not over mix, I just mean to get everything incorporated, then stop beating. You don’t want to whip it together, then turn your mixer on high and keep mixing for another 5 minutes. That will alter the texture and cause your cupcakes to not bake up as beautifully as they do with just a quick mixing of the ingredients together. Good luck!

      And…thanks so much for your comment! XO

  20. becca says:

    hey brooke! thanks so much for your response! i’m going to try to make these with my boyfriend :) he had cocoa powder but didn’t know what to make with it. but now he does! <3


  21. Danielle says:

    Hi there!

    I was making your frosting this weekend and it was definitely very tasty, but sadly it was super runny. It just never thickened up. I just wanted to make sure that the quantity of the heavy cream is correct. Do I really use 2 cups of heavy cream?

    Thanks :)

    • Brooke says:

      Absolutely! The cream is the trick! Hmmm….let me get back to you with some possible explanation on why it didn’t thicken. So sorry!

  22. Northwest Kirsten says:

    Holy cow. This frosting is the best ever. Will have to try it without the cocoa for for a vanilla version. I don’t really like traditional frosting — just too dang sweet and not creamy enough. This was good enough to put in a bowl and eat as dessert itself. Devoured by everyone I shared it with.

    You’re genius. I love every recipe I’ve ever made from your site.

    My 10 year-old just requested your Tres Leches cake for his birthday. That boys has him some good taste. Just saying.

  23. Shruti says:

    How many ounces are 2 baking squares? Ghiradelli squares are 1/2 ounce each and Baker’s ones are 1 ounce each…

  24. […] by Cupcake Inspiration on February 28, 2013 School’s Out Chocolate Cupcakes recipe via cheekykitchen […]

  25. Tony says:

    Hi:Thanks for the website to check on niuoittrn data and also for the carb data for this recipe. I’ll try this recipe today! I appreciate this information and will pass the website on to other diabetic friends. You’re the best!

Leave a Reply