Sweet & Savory Stuffed Acorn Squash Dessert {Not My Mother’s Stuffed Acorn Squash}

Squash for DESSERT? HUH! Yep, squash for dessert. This is no ordinary squash. It’s like a pumpkin pie and a pecan pie had little single-serve babies. But better!

I think my mother was having a genius moment when she served acorn squash stuffed with brown sugar, cinnamon, butter, Saltine crackers, and pecans. Seriously, can you think of any better way to get a kid to eat squash? I’ve modified her recipe quite a bit from what I remember, from decades ago, with the addition of dried cherries and extra filling making it perhaps a bit healthier, but every bit a dessert as her original recipe.

Supplies

• Shallow microwaveable dish, preferably with lid, to fit 2 acorn squash halves.
• Large sharp knife
• Shallow baking dish
• Spoon
• Fork
• Skillet to brown pecans on the stove
• Two 2-4 cup (medium) sized bowls. One needs to be microwaveable.

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Ingredients

• 1 acorn squash
• 1/3 cup cooked potato smashed with a fork. I microwaved an Idaho potato, peeled the skin and mashed when cooled.
• 1/4 cup water
• 1/2 cup pecans, toasted, chopped & divided
• 2 tbsp dried cherries, coarsely chopped. I use Mariani dried cherries.
• 3 tbsp butter divided (salted is fine)
• 1/4 tsp salt
• 1/4 tsp black pepper
• 6 Ritz crackers, or butter/club crackers, crushed into bite sized pieces.
• 2 Saltine cracker squares (optional) crushed into bite sized bits and pieces.
• 2 tbsp brown sugar
• 1/2 tsp cinnamon, for the topping
• 1/4 tsp cinnamon for the filling
• 1/2 tbsp olive oil - enough to drizzle over tops
• 2 tsp real maple syrup, divided. (Optional, but a great addition!)
• Vanilla Ice Cream optional

Step 1: Prepare and Pre-cook Your Ingredients

1. Wash and dry your raw acorn squash and potato. (You can use leftover cooked potato if you have any!)
2. Very carefully cut your squash. If they are large and you are creative you can cut it into nearly equal thirds. They work best if you cut them in half because the filling stays in nicely.
3. Scoop out and discard the seeds and stringy squash guts.
4. Test the squash and see how flat they will sit. You can shave off the high spots on the bottom to make them sit flat in the dish.
5. Score the insides of the squash, but don’t cut all the way through.

Step 2: Pre-cook the Squash and Potato

1. Poke a few holes in the potato and sprinkle with salt.
2. Sprinkle a little salt and pepper on the insides of the squash. Place cut sides down in a microwaveable dish with 1/4 cup water. If you can fit the potato in with it, go ahead.
3. Microwave until they start to get nice and soft. Gently squeeze with tongs or poke with a fork or knife to see if they are soft. They will need to be soft enough that you can scoop out most of the flesh, but not totally squishy, and the potato is soft enough to mash up with a fork.

Step 3: While the Squash Is Cooking, Prepare the Filling and Topping

1. Toast the chopped pecans in a skillet just until browned and aromatic and set aside to cool.
2. Combine brown sugar, 1/2 tsp cinnamon, crushed crackers and 2 tbsp butter in a small bowl.
3. Add 1/4 cup of the cooled, chopped pecans to the bowl with the crushed crackers mixture.
4. Stir gently to combine, but don’t mash up the crackers too much. There should be nice bite sized pieces.
5. Microwave in 30 second increments stirring gently, just until the butter is melted and evenly distributed.

Step 4: Prepare the Filling & Preheat the Oven or Grill

1. Coarsely chop the dried cherries into bite sized bits and add to a small to medium sized bowl.
2. Add 1 1/2 tbsp butter to the bowl with the chopped cherries.
3. Add 1/4 cup chopped pecans, 1 tsp maple syrup, 1/4 tsp cinnamon and a small pinch of salt and pepper.
4. Preheat your oven or grill to 450°. *Alternatively, you can use your broiler.
5. If the potato is cool, peel and discard the skin. Mash some potato with a fork until you have about 1/3 cup and add it to the bowl with the cherries.
6. When the squash is cool enough to scoop out the flesh, gently scoop most of the squash out and add it to the bowl with the cherries. Leave enough squash in the skins so that the squash maintain their shape.
7. Stir to combine. Taste and adjust for salt. If you like it sweeter, add another dash of maple syrup, or a small pinch of brown sugar. *A small dash of nutmeg is wonderful in this filling too!

Step 5: Assemble the Stuffed Squash

1. Place your squash in an oven, grill or broiler safe dish and sprinkle with a bit of salt and pepper. Just a little bit.*If the squash won’t set flat, use rolled up foil, or foil balls to hold them up so the filling won’t fall out.
2. Evenly distribute your cherry & squash/potato filling among the squash pieces.
3. Using the remaining bit of butter, dot the tops of the squash filling.
4. Drizzle half the olive oil over the tops.
5. Distribute half of the topping mixture over the tops pressing down to secure it to the filling.
6. Distribute the remaining topping over the tops, pressing gently and drizzle with the remaining maple syrup and olive oil.

Step 6: Cook Until Nicely Browned

1. Broil or bake until the tops are golden brown. The topping will turn into a hard crunchy crust over the cherry and pecan filling! It won’t take too long, maybe ten to fifteen minutes if baking, or five minutes if you are broiling. If you are broiling, keep an eye on them because the sugar and nuts will burn quickly!
2. Allow the squash to cool for at least ten minutes. It will hold it’s heat for a long time and the topping can burn you if you attempt to eat it right away.
3. Serve with a scoop of vanilla ice cream sprinkled with cinnamon or whipped cream if you are feeling extra fancy!

The nutrition label photo shows two servings but depending on the size of your squash, you can easily get four servings out of one squash if you cut the halves in half again when serving. They are very filling, especially with a scoop of ice cream on top!

Enjoy!