Lottie + Doof + Floriole Dinner (Pineapple Upside-Down Cake)

As you probably know by now, Chicago was hit by a pretty intense blizzard this week. It came just as we were preparing for the first Lottie + Doof and Floriole dinner. We decided to go ahead with the first dinner as planned and were cheered by a great group of people who braved the cold and mountains of snow to eat dinner with us. As a food writer, I spend a lot of time behind the safety of my computer and it was a real treat/challenge to have what happens in the privacy of my kitchen happen in real time and space. It turned out to be such great fun that I can’t wait to do it again.

Before we talk about the dinner, some gratitude. I can’t thank the staff at Floriole enough (Sandra, Mathieu, Amber, Claire (both of them), Heather, Kaitlyn, and Rachel (and everyone else who lent a hand outside of the event)) for their hard work and for allowing me the privilege of working with them. Thanks to the very good people of the Wisconsin Milk Marketing Board who sent us incredibly delicious cheese from Saxon Creamery, BelGiosio and Bleu Mont Dairy. I can honestly say that Wisconsin cheeses are one of the best things about this world. And most importantly, thanks to everyone who came out in the cold to share this hearty Midwestern menu with us.

Most of the recipes we used are from the archives of this site, though improved by Floriole’s expert staff. They included the charred onion dip, which we served with housemade potato chips. My favorite potato gratin dish, as well as the famous apple jellies, also made it onto the table. A couple of recipes (including the beautiful green goddess salad) will make their way here soon.

One of the new recipes, developed especially for the dinner, was a Pineapple Upside-Down Cake with Pink Peppercorn Ice Cream. Sandra had the idea for the pineapple cake, which immediately made me think of Claudia Fleming’s recipe for pineapple with pink peppercorns. I set about making an ice cream that had a bit of the floral pink peppercorn flavor but also the tang of buttermilk. Together, the plate was fantastic (if I do say so myself!). I’m hoping the pineapple cake makes it into the bakery case at Floriole on a regular basis (hint, hint).

Both dinners were great experiences and I’m very happy to say we will be doing this again. We’re hoping to collaborate together once a season, so look for a spring dinner in May. In the meantime, make this cake. You’ll be glad you did.

Pineapple Upside-Down Cake (adapted from a Rose Levy Beranbaum recipe)


  • 6 Pineapple rings (1 whole, 5 halved)
  • 11 Brandied Cherries (or maraschino)
  • 4 tablespoons butter
  • 1/2 cup firmly packed brown sugar


  • 3 egg yolks
  • 1/2 cup buttermilk
  • 1 teaspoon vanilla
  • 1 1/2 cup unbleached all-purpose flour
  • 2/3 cup granulated sugar
  • 3/4 teaspoon baking powder
  • 1/2 teaspoon salt
  • 9 tablespoons butter

Butter a 9-inch cake pan and line the bottom with parchment, butter parchment. Set aside.

Preheat oven to 350°F.

To Make Fruit Topping
Drain pineapple slices (reserving 1 tablespoon of juice) and cherries and place on paper towels to absorb excess moisture. You will need 1 whole pineapple slice and 11 whole cherries. Halve the 5 remaining pineapple slices.
In a skillet, stir together the 1 tablespoon pineapple juice, the 4 tablespoons of butter and the 1/2 cup of brown sugar, until the sugar has dissolved. Simmer on medium/low heat 3 minutes, stirring constantly just until it starts to bubble. Continue simmering until deep amber and caramelized (an instant read thermometer will be 300°F.) Remove from the heat immediately and pour the bubbling caramel evenly into the bottom of the prepared pan. Without touching the hot sugar, carefully place 1 whole pineapple slice in the center of the pan and 10 half slices surrounding it, like the spokes of a wheel. Place the whole cherries in the center of the whole pineapple slice and between each half.

To Make Cake Batter
In a medium bowl, lightly combine yolks, about 1/4 of the buttermilk, and the vanilla.
In a large mixer bowl, combine the dry ingredients and mix on low speed for 30 seconds to blend. Add butter and the remaining buttermilk. Mix on low speed until dry ingredients are moistened. Increase to medium (high speed if using a hand mixer) and beat for 1 1/2 minutes to aerate and develop cake’s structure. Scrape down the sides. Gradually add egg mixture to batter in 3 batches, beating for 20 seconds after each addition to incorporate ingredients and strengthen structure. Scrape down the sides. Scrape batter into fruit-lined pan, smoothing evenly with an offset spatula. Bake for 40 to 50 minutes or until golden brown and the wire cake tester inserted in the center comes out clean and the cake springs back when pressed lightly in center. Run a small metal spatula around the sides and invert at once onto a serving plate. Leave the pan in place one or two minutes before lifting it. If any fruit has stuck to the pan, simply use a small spatula to place it back on the cake.

*For fresh pineapple, use 1 golden pineapple peeled and cored. Cut pineapple into 6 1/2-inch thick slices, reserving 1 tablespoon of juice. Trim the diameter of the pineapple slices to approximately 3 inches wide.

Buttermilk Pink Peppercorn Ice Cream

  • 2 cups heavy cream
  • 3/4 cups granulated sugar plus 1/3 cup granulated sugar
  • 1/4 cup pink peppercorns, lightly crushed
  • 8 large egg yolks
  • 2 cups buttermilk
  • 1/2 teaspoon pure vanilla extract
  • pinch of salt

In a medium saucepan, heat cream and 3/4 cup sugar to a simmer, stirring until sugar has dissolved. Remove from heat, immediately add peppercorns and cover. Allow to steep for 1 hour. Strain cream into another medium pot (or the same one, cleaned) and warm over low heat. In a medium bowl, whisk egg yolks and 1/3 cup sugar. Slowly add the warm cream into the eggs to temper, whisking constantly. Once all of the cream has been added return the custard mixture to the pan and warm over a medium low heat until the custard has thickened and coats the back of your spoon. (this will be around 170-175°F) Immediately remove from heat and pour into a medium bowl. Add the buttermilk, vanilla and salt and stir to combine. Cover and chill overnight. The next day, stir the mixture before churning it in your ice cream maker according to manufacturer’s instructions.

24 comments to “Lottie + Doof + Floriole Dinner (Pineapple Upside-Down Cake)”

  1. Tim!

    Ed and I had a BLAST last night –thanks so much again for the wonderful hospitality and food! That pork was divine…Ed’s a picky eater and even HE cleaned his plate. Great work!!!

  2. Yowza I’m sorry to have missed this!

  3. I’m determined to get tickets next time around. I was sad I was too slow this time!

  4. This looks so fabulous! I only wish I was an itty bitty bit closer to Chicago so that I could come and join in the fun. Charred onion dip + housemade potato chips look divine, naughty, wonderful.

  5. How lovely! I expected nothing less.

  6. looks like it was a lovely event, even amidst the “snowpocalypse!” Congrats!

  7. It was so wonderful, Tim — all of it. Good to see you. Let’s talk soon.

  8. sounds like everyone was so happy to be @ this wonderful event & partake in such fabulous fare!
    thx for the pineapple upside-down recipe!…like the brandied cherries ingredient!

  9. Thanks for a great time, delicious food & terrific music! We will do it again! Come and see us!

  10. Very, very nice. Everything looks and sounds like it was great.

    Tim, what is your favorite source for pink peppercorns? Thanks!

  11. Thanks for all of the friendly words! Glad to see some who attended the dinners checking in. Whitney and Janine, we’ll see you next time!
    Pam, I like the pink peppercorns that The Spice House sells. They have a website. We actually found through the course of making/testing these recipes that different sellers (and even different batches from same seller) have different intensities. Makes it a little hard to plan for. You can taste the ice cream base before straining out the peppercorns to try determining if the flavor level is right, and then steep longer if you’d like more pepper. (keeping in mind that flavors will be duller when frozen)

  12. Jess Gordon says:

    February 4th, 2011 at 2:31 pm

    Looks amazing! so great that you collaborated with Floriole. I will have to come next time around. Keep me posted.

  13. What an amazing dinner! Too bad the San Francisco Bay Area is not closer to Chicago. I am impressed by the guests that braved the bad weather. Nicely done!!

  14. Congratulations! I so wish I could have been there. Now I am left hungry and envious.

  15. Did you actually make it in the skillet, or transfer the hot sugar to the parchment lined 9 inch cake pan? I’m hoping that you answer- the skillet- because that’s less work, and I like that.

  16. Hi Suzanne,
    I am here to dash your hopes. I made it according to recipe. You can make it in a 10-inch cast iron skillet, but that isn’t what I did. I like the straight sides of a cake pan. If you do it in the skillet, cook the caramel for just a couple of minutes because it will continue to cook off heat.

  17. Wow, looks like an amazing dinner! And beautiful pictures as always.

  18. Wow, Tim, this looks + sounds amazing! I am excited to try my hand at the pineapple upside-down cake!

  19. Love this recipe, just a few questions though…

    Place the whole cherries in the center of the whole pineapple slices..all of the cherries go in the middle of the one slice? Or a cherry in each half-center?

    Topping: pour in buttered and lined 9-inch cake pan
    Cake: “Scrape batter into fruit-lined skillet”

    As per your earlier post, I’m guessing that the batter goes in the 9 inch pan?

    Does a non-stick 10-inch work here?

    I grew up on homemade potato chips…:-)

    Thanks so much.

  20. Hi Melanie,
    Ugh. Sorry for all of those typos. I think I corrected it now.
    Yes, everything as you assumed. 10-inch non-stick should work fine (although I haven’t tried), the cake will be pretty flat in that sized pan, but I think it will work. Still use parchment.

  21. Oh man, I can’t believe I missed this. The menu looks amazing. I suppose that for your spring dinner you wouldn’t consider maybe making the menu a little more vegetarian/pescatarian friendly?

  22. Katie, thanks! The menu was totally vegetarian friendly, with the exception of the piece of pork. We substituted a really lovely vegetable tart for anyone who didn’t want to eat meat. Hope to see you next time!

  23. Stunning!! brilliant idea to pair pink peppercorns with ice cream and pineapple upside down cake!

  24. Ambika Kumar says:

    August 6th, 2012 at 9:34 pm

    Hi, i love your blog and this looks like a fantastic recipe:)
    I am baking this cake for a surprise birthday party for a friend tomorrow and i have a couple of questions….
    For the caramel topping can i use white sugar instead of brown?
    And how long can this cake sit out? Will it become too soggy if i bake it in the morning for the evening party?

What do you think?