Apple-Stuffed Acorn Squash

End of summer vibes again. The light is changing. The mornings are cooler. School is starting — you can tell because the Wauwatosa traffic picks up and the kids on the block are wearing backpacks and looking miserable. I don't miss school. I do miss Danny at school. But that's a different kind of missing. Brewed the rye saison on Tuesday. It's an interesting beer to make — saison yeast is wild and temperamental, fermenting hotter and drier than most strains. You have to let it do its thing and trust the process. The rye malt adds complexity: spicy, bread-like, with a dry finish that plays well with the saison character. First samples were promising — dry, peppery, with a rye backbone that felt uniquely mine. I also brewed a batch of the Fireside winter warmer — year two. Same recipe, minor tweaks. It's becoming a tradition at the brewery, which is a strange thing to say about a beer I invented last year. But traditions have to start somewhere. At home, I threw a dinner party. An actual dinner party. Six people: Kevin, two brewery guys (Marcus and a new hire named Leo), a woman from the taproom staff named Jess, and Danny's sister Sarah, who's home from college for the summer. I haven't mentioned Sarah before because she's always been Danny's little sister — three years younger, quiet, sweet. She's twenty now, at UW-Madison studying psychology. I invited her because she messaged me about the Milwaukee Record article and said, "Danny would have been so proud of you, Jake." And I thought: she should be at my table. The menu: slow-roasted pulled pork, coleslaw, cornbread, baked beans, and a cherry cobbler for dessert. A barbecue spread. My kitchen was chaos — six people don't fit in my apartment easily, so we ate on the balcony, passing plates across the grill. It was loud and messy and perfect. Sarah said the cobbler was amazing. I said it was just canned cherries and a biscuit topping. She said, "That's what makes it amazing. You made something out of nothing." She sounded like Danny when she said it. Same cadence, same quiet honesty. Sunday at Babcia's: racuchy — apple fritters, late summer edition. The apples are coming in from the orchards. The year is turning. The fritters are perfect. The tradition continues.

The apple fritters at Babcia’s got me thinking about what else I could do with the early orchard apples piling up on my counter. This stuffed acorn squash hits that same sweet spot—warm, simple, the kind of dish that tastes like the season turning. It would’ve fit right in on the dinner party table next to the pulled pork, and honestly, Sarah probably would’ve said the same thing she said about the cobbler: you made something out of nothing.

Prep Time: 15 minutes | Cook Time: 55 minutes | Total Time: 1 hour 10 minutes | Servings: 4

Ingredients

2 acorn squash, halved and seeded
2 tablespoons butter, melted
2 medium apples, peeled and diced (Honeycrisp or Granny Smith)
1/4 cup brown sugar, packed
1/4 cup dried cranberries
1/4 cup chopped pecans
1 teaspoon cinnamon
1/4 teaspoon nutmeg
1 tablespoon maple syrup
Pinch of salt

Instructions

Preheat the oven. Set your oven to 400°F. Line a baking sheet with parchment paper or foil.
Prep the squash. Brush the cut sides and cavities of the acorn squash halves with melted butter. Place cut-side up on the baking sheet and season lightly with salt.
Make the filling. In a bowl, toss the diced apples with brown sugar, dried cranberries, chopped pecans, cinnamon, and nutmeg until evenly combined.
Stuff the squash. Divide the apple mixture evenly among the four squash halves, mounding it into the cavities. Drizzle each with maple syrup.
Bake. Cover the baking sheet loosely with foil and bake for 40 minutes. Remove the foil and bake for an additional 15 minutes, until the squash is fork-tender and the filling is golden and bubbling.
Serve. Let cool for 5 minutes before serving. Pairs well with roasted pork or as a standalone side dish.

Nutrition (per serving)

Apple-Stuffed Acorn Squash — When the Year Turns and the Apples Come In