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First of all – I need some dining advice. We will be going to New York City in May! I’m so excited! My husband is a big baseball fan, and since this is the last year before they tear down Yankee Stadium, we figured this would be a perfect excuse to go. I’ve been to New York twice before, but it has been a little while, so right now I am just getting over the shock at how expensive hotels are. So we are looking for places to eat. Inexpensive places to eat. We might have one nice dinner or lunch, but we’re already breaking the bank with hotel and baseball tickets!! So any suggestions are definitely welcome.

When I mentioned that I would be posting a lot of cupcakes this year, I really meant it!! Although it is more of a mini cake to me than a cupcake, the book still calls them cupcakes so I will stick with that.

Sometimes when it is a work birthday, I will ask the birthday person a couple of days before their birthday what their favorite kind of cake or treat is. This particular co-worker said he didn’t really have any preferences, but then he mentioned pineapple upside down cake. I can’t remember the last time I had pineapple upside down cake, and I don’t think I had ever made it before. So while looking through some cookbooks that night, I came across this recipe for Pineapple Upside Down Cupcakes! Even better than making a whole cake!! These cupcakes are made in jumbo muffin pans. I didn’t have a jumbo muffin pan, so I ended up buying one. It holds 6 muffins, but I would buy an extra one next time so I could make 12 at a time, because it was kind of a pain with only one pan.

These were so good. At the bottom of the pan, that became the top of the cupcake when flipped out of the pan, it became a gooey glazed topping. The cupcake was extremely moist, and the pineapple slice added the perfect amount of pineapple flavor to the whole thing. The recipe says you can serve the cakes with whipped cream, but I think they are perfect just plain!
Pineapple Upside-Down Cupcakes
from cupcakes!

Pineapple Topping
6 tablespoons unsalted butter
2 tablespoons light corn syrup
1 cup packed brown sugar
12 pineapple slices (one 20-ounce and one 8-ounce can pineapple in its own juice), drained

Easy-Mix Yellow Cupcake Batter for 12 extra-large cupcakes (see below)

Posistion a rack in the middle of the oven. Preheat the oven to 350F. Line the bottoms of 12 jumbo muffin tins with wax paper circles. Spray the inside of each cup with non-stick spray.

Make the topping – In a medium saucepan, combine the butter, corn syrup and brown sugar and cook over medium heat, stirring occasionally, until the mixture is smooth and the sugar is dissolved. Remove from the heat.

Make the cupcakes.

Put 1 tablespoon plus 1 teaspoon of the brown sugar mixture in the bottom of each muffin tin. Put a pineapple slice on top of the brown sugar mixture. Spoon a generous 1/3 cup of the cupcake mixture over the pineapple slices. The batter will come just to the top of each muffin cup.

Bake until the tops feel firm and a toothpick inserted in the center comes out clean, about 25 minutes. (When inserting the toothpick, do not enter the whole way down into the pineapple). Cook the cupcakes for 5 minutes on a wire rack.

Use a knife to loosen the cupcakes. Place a wire rack on the top of the pan and flip the pan over carefully. Leave the cupcakes upside-down to cool completely.

Easy Mix Yellow Cupcake Batter
*this recipe is for 12 extra-large cupcakes

2 1/2 cups unbleached all- purpose flour
1 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
2 large eggs
2 cups sugar
1 cup canola or corn oil
2 teaspoons vanilla extract
1 cup sour cream

Sift the flour, baking powder, baking soda, and salt into a medium bowl and set aside.

In a large bowl, using an electric mixer on medium speed, beat the egg and yolk and sugar until thickened and lightened to a cream color, about 2 minutes. Stop the mixer and scrape the sides of the bowl as needed during mixing. On low speed, mix in the oil and vanilla until blended. Mix in the sour cream until no white streaks remain. Mix in the flour mixture until it is incorporated and the batter is smooth.

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28 Responses to Pineapple Upside Down Cupcakes

  1. Jessy and her dog Winnie says:

    That looks delicious! I love pineapple!

  2. Mary says:

    Pineapple upside down cupcakes sound amazing! And they look really tasty!

    My sister lives in New York and last time I visited we mostly went around to all the different fancy chocolate shops and had 1 or 2 at each one. I really liked the windows at Teusher (chocolate shop). Murray’s cheese shop at Grand Central Station (the big train station) is worth going to see too. And definitely hit Junior’s for cheesecake. I think we mostly snacked our way through. We did go to Patsy’s for dinner and that was excellent.

  3. Peabody says:

    An excellent idea…make it portable. I love pineapple upside down cake.

  4. Katie B. says:

    I love love love fruit upside-down cakes!!! Man, I wished I worked in your office! 🙂

    Mind you, I’ve never done this, because I don’t have any candied ginger, but Alton Brown drops some in with the butter and sugar and fruit, before he pours in the batter… just for a nice zing!

    And as far as NYC, for us, a trip wouldn’t be complete without a stop at Grey’s Papaya… if you like cheap hot dogs, give them a try. (They’re like crack.) My favorite place is Norma’s, in the Le Parker Meridian hotel – they only do breakfast/brunch! Heaven!

  5. mimi says:

    those cucpakes look so moist!

    even though i can’t believe you’re actually going to see the yankees (instead of catching a game with who we all know will be the better team!) there are tons of inexpensive places here to find great food, and that’s why i love living here! my first suggestion for a nice dinner is noodle pudding for italian. yes, it’s in brooklyn, but if it’s a nice day you can walk across the bridge. super delicious italian food at very reasonable prices! have fun!

  6. Susan from Food Blogga says:

    This post makes me think of my dad: he’s going to Yankee stadium in Sept. when they play the Red Sox (go Sox!) and upside down pineapple cake is his #1 dessert. He’d love these miniature ones, for sure. They look deliciously adorable, Deborah.

  7. glamah16 says:

    Youll have so much fun in Nyc. Cant wait to read of your travels.

  8. Happy cook says:

    Yumm Delicious.
    Love the colour and the freshness of the cake;

  9. Madam Chow says:

    These look fantastic!
    As for dining advice – you should head over to Ivonne’s blog, Cream Puffs in Venice. She’s going to NYC, too, and asked for suggestions in her latest posting, and people are giving her a lot of feedback. Also check out Kathy’s blog, A Passion for Food. She lives in NYC and is constantly reviewing places to eat.

  10. linda says:

    Cute, a pineapple upside down cupcake instead of cake.

  11. Gabi says:

    Yummy and just the perfect size!
    Wow I wished you worked with me…
    x x x

  12. Cakespy says:

    Ooooh, I haven’t had this for so long–it looks so good!! And way to take away the stress of flipping!

  13. Melanie says:

    Pineapple upside down cake is one of my favorite desserts! Can’t wait to try the mini-version. They look so moist and delicious.

  14. Birdie says:

    Love the cupcakes. Thanks for your comments on my site as well. I’m new to blogging and actually writing down my recipes and it’s always nice to hear positive feedback. I love your site and visit often. You take really good pictures

  15. Steph says:

    Yum! These look beautiful and delicious!

  16. Catherine Wilkinson says:

    What??? Get out of town! These are AMAZING! Oh, my son would go nuts for these…he loves pineapple upside down cake, but he’s in Iraq right now, and is lucky to get a gumball! But when he gets home….!

  17. Cookie baker Lynn says:

    Pineapple upside down cupcakes – genius!

  18. Tarah says:

    Mmm, that looks so good! I love pineapple!

  19. ~Madeline~ says:

    These are absolutely perfect! I’ve been looking for something exactly like this for a while now. I wanted to make individual cakes and I can’t wait to try these.

  20. Gretchen Noelle says:

    I love pineapple upside down cake! I cannot wait to try these!

  21. PheMom says:

    I read about this the other day and thought you might find it an interesting option for your trip if it works. (And the pineapple upside down cupcakes are BRILLIANT! 🙂


  22. Kevin says:

    I keep hearing about pineapple upside down cakes but I still haven’t had one. It looks really good. Bookmarked to try.

  23. taste memory says:

    luv pineapples in pastry – upside down looks tempting!

    momofuku’s is a can’t miss when in nyc….there is a great italian bakery right across the street for cookies & espresso afterwards.

    of course WHOLE FOODS was practically my living room the last time i was in new york – no WF where i’m at..have fun!

  24. Gigi says:

    Pineapple perfection! I love it, mini pineapple cake.

  25. Shandy says:

    OMGoodness! These huge pineapple upside down cupcakes look absolutely delicious! You are one of the sweetiest people. Your co-workers must all look forward to their b-days just to see what you’ll will bring.

  26. ruthEbabes says:

    I love pineapple upsidedown cake! How creative to make cupcakes out of this!

    Looks fab!

  27. Anonymous says:

    I made these last night and they are fantastic! The sour cream in the cake batter adds to the moisture of the cupcake. I’m a huge fan of using sour cream in baked goods, so when I came across this recipe I was really excited! Also, I added a cherry to the midde of the pineapple ring. They are adorable!

  28. Amelia says:

    I just made these tonight and they were fantastic! Even though they were quite large, people had seconds. Thank you for posting this recipe!

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