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Maple Dijon Acorn Squash with Apples + Chard

Active Time: 15 minutes
Total Time: 40 minutes
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Why we love it:

PSL seems to make its way into everything earlier and earlier every year, but maple, apples, and squash is a combination that truly means early Fall in my kitchen! This meal is fancy enough for guests but simple enough to pull off on a weeknight. It’s sure to say It’s Back to School, leaf peeping time, and planning Halloween costumes while you’re enjoying the flavor combination. *This dish is longer than our usual in the oven but short on active time, so plan accordingly!


  • 2 Acorn Squashs
  • 2 Apples (fuji, granny smith, gala, etc.)
  • 12 Red Onion
  • 2 bunches Green Chard (or red, swiss, or rainbow)
  • 1 Tablespoon Maple Syrup
  • 1 Tablespoon Dijon Mustard
  • 1 teaspoon Soy Sauce
  • 1 Tablespoon Extra Virgin Olive Oil (divided)
  • 1 teaspoon Kosher Salt (divided)
  • 2 Tablespoons Unsalted Butter (divided)

Cooking Instructions

  • 2. SQUASH

    Cut the squash in ½ and scoop out their insides. Make shallow slashes in the flesh with a paring knife - about 6 - 8 per squash half.

    Place them cut side down on a lined baking sheet, then carefully use a paring knife to make a few slashes in the thick skin on each one. Place into the oven. Roast for 10 minutes then we’ll return to them.

  • 3. CHARD + APPLE

    Slice the apples into thin slices, then cut those in ½ so you have thin square-ish shapes. Set aside.

    Small dice ½ of the red onion.

    Wash the chard leaves and shake off any excess water (a little clinging on is ok). Use your thumb and forefinger to strip the leaves off of the stems. Stack the stems together and trim off the very bottoms, which are usually quite woody and sometimes split and brown. Discard that part. Slice the stems into thin half-moons, like you would celery. Place these with the apple and onion.

    Stack the leaves and slice or tear them into approximately 2” squares. Set aside in a separate container.

  • 4. GLAZE

    Whisk together the maple syrup, dijon, and soy sauce.

  • 5. SQUASH PART 2

    Remove the pan from the oven and carefully flip the halves over. Drizzle each one with about ½ teaspoon of olive oil and about a ¼ teaspoon of salt per squash.

    Evenly pour the glaze into the center of each. Use the back of a spoon to spread the glaze up the sides of each piece, but it’s ok to let it pool up in the bottom.

    Dot the center with the butter, reserving just 1 teaspoon for the chard sauté.

    Return the pan to the oven and roast for another 25 - 30 minutes. During this time, you can baste the centers of the squash with the glaze using a spoon once or twice. It will start to absorb and evaporate though, which is what you want!


    When the squash have about 8 minutes left, start the side dish.

    In a large sauté pan, over high heat, melt the last teaspoon of butter. Then add the onions, apples, and chard stems. Add a pinch of salt and sauté for about 5 minutes until everything is softening up.

    Add the chard leaves and toss in the pan pretty much constantly for 2 minutes until the leaves are wilted and soft. Turn out into a serving bowl or place directly on plates.

  • 7. SERVING

    Serve the chard and apple sauté topped with a squash. If you’re feeling festive, add an additional dot of butter to the center of each squash before serving and let it melt there.

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    the only gluten would be in the soy sauce so be sure to use Tamari
    delicata squash are very good and you do not need to peel them! you can use cubes or wedges of butternut squash instead
  • CHARD:
    any variety of chard works well. Spinach, kale, or broccoli rabe would be a good sub if preferred
    if you aren’t into the sugar, you can omit the maple and add miso or tahini instead. You can also just omit it and add nothing else
    delicata squash halves will cook in 20 minutes! Or you can slice the acorn squash into 2” thick wedges and brush them with the glaze occasionally as they bake - wedges will cook through in about 15 minutes
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