Pineapple Hand Pies

I was strolling through Target the other day.  It should have been a five minute visit, but I usually need to set about an hour aside because I know I’ll end up taking a slow walk through, checking the clearance racks and to see what’s new on the shelves in the main aisles. If you’re a Target fan, you know what I’m talking about…

I have a personal trail that I follow, which, if it’s during a holiday season, will always start in the back corner where they have the seasonal merchandise on display. I end up walking around the middle of the store, through the housewares department, and then end up at the kitchen and dining department, which is where I spend a lot of time.  The outer aisle shelves are also stocked with holiday themed merchandise.  That shelf was looking pretty picked over, and I was about to walk away, when on the bottom shelf two lonely little yellow dishes with the word “yum” printed on them, caught my eye.

I stopped.
I picked one up.
I ran my finger over the “yum”, thinking how absolutely adorable it was.
I wondered what I would do with the dish.
I couldn’t come up with an answer.
And then I put it back.


You know that there is that point of no return, that, if you make it far enough away, say… maybe 50 feet… there is a good possibility that you won’t be leaving the store with the item. I made it about 20 feet, and all of a sudden I was turning the cart around, and those plates were in my cart before my brain knew what was happening.

There is no fighting it.
You know…that impulse purchase.

So, on the way home, I was thinking about which dessert makes me say “yum”.  My mom makes this outstanding pineapple pie. I LOVE that pie, but I was quite certain that whatever I made to put on those dishes had to be chocolate based. I thought about chocolate cream pie.  I thought about molten lava cakes.  Fudgy brownies with raspberries drizzled with chocolate sauce and whipped cream.  Nope.  My brain kept going back to that pineapple pie. I kind of knew that it was hopeless… so I decided to make pineapple hand pies.  I’m not sorry.  I’ve eaten two of them.  They are delicious.


Pineapple pie has to be the easiest pie to make… yep…even easier than chocolate cream pie!  It takes no time to throw the ingredients in the pan, the crust together, and by the time you’re finished rolling it out, the pineapple is ready to be poured into the shell.  Top it with the other crust,  throw it in the oven for a half hour, and before you know it, you’re eating this sweet, gooey, pineappley deliciousness.

I can honestly say that this is one impulse buy that I have zero guilt over, and that makes me very happy…..very stuffed and about 2 pounds heavier after today…. but very happy.  Life is good with pineapple pie… Yum.


Pineapple Hand Pies
(Makes 20 individual hand pies)

Preheat oven to 350 degrees.   Line a baking sheet with parchment paper.

Aunt Linda’s Pie Crust
You will need to double this recipe. I suggest doing it in two separate batches.

This is my Aunt Linda’s recipe…I truly adore her.  When we were younger, my cousins and I used to fight over whose aunt she really is.  They used to insist that Aunt Linda was their aunt (which she is), but I really wanted her to be my aunt too (and she is)..  It’s funny to think about it today, but back then it was a battle!  Aunt Linda had no clue how we fought over her.  Well, now she does… (love you!) and I’d still fight today if I had to, just to have her as my aunt!

2 cups flour
1 cup shortening
½ tsp salt
½ cup milk
1 tbsp vinegar (I prefer cider vinegar, it tends to give the crust a good flavor)

In a small bowl, mix the milk and vinegar together.  Set aside. In a large mixing bowl, blend the flour, shortening, and salt together until mixture is in pea size crumbles. Pour the milk and vinegar mixture into the flour mixture and stir.   The dough will be sticky.

Divide the dough in half, and using a generous amount of flour on the rolling surface, roll the dough out to about 1/8” thick.  Using a round template that is about 5 – 5 ½” in diameter, cut circles out of the dough.  Repeat until you have 10 circles of pastry from each batch of dough.


The Pineapple Filling
1 20 oz can crushed pineapple (do not drain)
1 cup granulated sugar
3 tbsp cornstarch
½ tsp salt
5 tsp butter

Combine the pineapple, sugar, cornstarch, and salt in a pan. Cook over medium flame stirring constantly until it comes to a boil.  Boil for one minute, and remove from heat.




Place one tablespoon of pineapple filling in the middle of each dough circle. Be sure that the filling is away from the edge of the dough circle so that it seals properly.  Place ¼ teaspoon butter on top of filling on each pie.  Fold one half of the circle over the filling, so that the edges meet up, and makes a half circle.  Seal the edges with a fork.  Cut a little design on the top of the pie.  I always do a heart.

Place each pie on the lined baking sheet.  Bake for about 20-25 minutes, or until golden brown.

Remove from oven and cool completely on cooling rack. Drizzle with glaze.

The Glaze:
1 cup confectioners sugar
1 tbsp butter, melted
2 tbsp milk

Mix the confectioners sugar, butter, and milk until well blended.  Drizzle over each pie.


Don’t forget to use your dough scraps to make these cinnamon swirl pastries found at the end of the Rustic Tomato Tartlet recipe…



18 thoughts on “Pineapple Hand Pies

      • I must give this a try some time. I have to accomplish my mission about not baking in one month as I will forget that I want to lose weight as soon as I smell something delicious is waiting inside the oven. Haha! But I promise to give this a try. I love Pineapple, too. 😉 Enjoy the rest of the week.

  1. Haha, I’m exactly the same in shops, defo an impulse shopper. Your plates are so cute, you made the right move buying them 🙂 I love pineapple but never had it in a pie! What a delicious idea, love the idea of them as hand pies as well. Will be giving these a go for sure

  2. I’ve never had pineapple pie and I know it must be so delicious. I have a special love for hand pies, yours are perfect. How much flour is in the pastry dough? It looks perfectly flaky and tender.

    • Oh you need to try these… they’re so simple. Just a few ingredients, and you’ll be enjoying a gooey goodness of pineapple!! If you like pineapple, then trust me, you’ll love these! Two cups of flour… thats all! The dough recipe is truly fail proof… ❤ Thank you for stopping by!! ❤

  3. I love Target. I always spend a little too long perusing the $1 racks right when you walk in the door, haha. There’s always something you can find at Target, even if you don’t need a thing! Thank goodness there’s no Target nearby me right now. These pies certainly look like they’d make me say “yum!”

  4. Pingback: Flaky Pineapple Squares – Holiday Recipe #7 | 365 Days of Thank You

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