Twice Baked Delicata Squash with Swiss Chard

Whether served as a main course or side dish, these little stuffed squashes are always a hit.

One of my favorite winter squashes is the sweet little Delicata. Their compact size, and quick cook, makes them a perfect weeknight dinner side, or even main course if stuffed! They have a sweet orange flesh, store well for a long time, and are loaded with vitamins and minerals. Another bonus, this winter squash has an edible peeling, so you will get some extra fiber as well.

            The Swiss chard has been magnificent this year, abundant, large leafed, and beautifully colored. A quick chop of a few leaves adds a nice dimension to this dish. You can substitute spinach or other green if you do not have the chard.

Pineapple sage

            I’ve used pineapple sage here because my plant in the garden is giant! If you’ve never grown this, look for it next year, a quick crush of the leaves imparts a lovely scent of both pineapple and sage, but it doesn’t add a pronounced pineapple flavor when cooked. If you can’t find it, substitute another fresh sage here, or any other herb you really love. Thyme would be lovely, or rosemary.

            I’ve added an organic vegan sausage to this for a little extra dimension, so this is perfect for a meatless meal night. Serve it with a nice salad for a full meal. To serve as a side for a larger gathering, you can slice them in half after the second bake and fill the platter, leaving a couple whole for those who want to make this their main course.

Twice Baked Delicata Squash with Swiss Chard

  • 2 Delicata squash
  • 2 tbsp. olive oil
  • 1 small yellow onion
  • 2 cloves garlic
  • 4 leaves Swiss chard
  • 1 tbsp. butter 
  • 2 tbsp. pineapple sage, minced
  • 2 organic vegan sausage patties, browned
  • 2 ounces dairy-free or traditional Cheddar
  • Few pinches of smoked paprika

Preheat the oven to 350 degrees and float a little water on a baking sheet.

Slice the squash in half lengthwise and remove the seeds. Place cut side down on the baking sheet and bake on the middle rack for 30 to 35 minutes, or until the flesh and peelings are tender. This will depend on the size and hardness of the squash. Remove from the oven and let cool until you can handle them. Scoop out the flesh into a bowl.

While the squash is cooking, heat a sauté pan over medium high and add the olive oil followed by the onion. Cook for a few minutes until softened, then add the garlic and the chard, and continue cooking until everything is softened. Mix in the pineapple sage just to warm.

Add the chard mixture to the flesh of the squash, season, and taste. Lightly season the shells as well. 

Stuff the squash shells with the mixture, break up the soy sausages and divide to the top of the shells, then sprinkle with the cheese and paprika.

Pop under the broiler or in a hot oven until the cheese is melted, and serve. 

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32 Comments Add yours

  1. Suzassippi says:

    Looks and sounds delicious!

    1. Thank you! It was really lovely, and delicious reheated the next day as well.

  2. Nancy says:

    I loved seeing this. I need to be more familiar with different kinds of squash… thank you!

    1. I have to admit, I am not the biggest fan of some of the really “squashy” hard winter squashes, although I eat them without complaint, but I love butternut and some of the new (old) more delicate flavored varieties such as Delicata and Sweet Dumpling. These I could eat all the time!

  3. Bernadette says:

    Dorothy, I am really liking these vegetable recipes you have been posting. I am not familiar with pineapple sage.

    1. Thank you Bernie! This is the magnificent time of bountiful harvest here, and I’m using what’s good and local and in great supply. Luckily, it all tastes wonderful!

  4. At first glance, I thought you’ve used mushrooms in the filling, which I thought is a great idea. Never tried vegan sausage, but it sounds like a perfect recipe for using them,
    Pineapple sage must have added such wonderful aroma here. 🙂

    1. Mushrooms would be GREAT here! The sage adds a nice element to this dish, but I know most folks probably can’t get their hands on it, but any sage will add beautiful flavor.

  5. It looks absolutely delicious 😋 That pineapple sage intrigued me 🌱 I love sage!

    1. It’s a beautiful plan Ribana. Lovely scent, and beautiful flowers. This year, mine grew really tall!

  6. Carolyn Page says:

    So many great textures and flavours in this one, Dorothy! And so nutritious, too.
    I’ve never heard of pineapple sage. I’ll have to investigate..

    1. I love pineapple sage, and even if it didn’t smell and taste great, I would grow it just for the flower, a beautiful scarlet!

      1. Carolyn Page says:

        We definitely have it in Oz. It will be a matter of asking when next I’m at the local nursery.
        The plant itself sounds gorgeous with its red flower. And with Spring upon us it’s just the right time to plant… 😉 😉

      2. Good luck in your quest, and don’t forget your ruby slippers!

  7. My husband is not a squash guy, but I love it. This looks delicious.

    1. Thanks Judy, they were really good!

  8. Gail says:

    I get excited when I see all the varieties of squash this time of year. 🍁🍂🌾

    1. I know it! They are as delicious as they are pretty!

  9. I have been craving winter squash lately and this sounds perfect, thanks Dorothy!

    1. You’re welcome, it satisfies the craving!

  10. Chef Mimi says:

    Love love this. Except for the vegan sausage and fake cheese 🤣 Delicatas are so good. I forgot to plant them this year.

    1. Thanks! I think it’s been a great year for these little treasures!

  11. This looks amazing!!

    1. Thanks! So glad you stopped by!

  12. Another amazing sounding dish.

  13. CarolCooks2 says:

    I use sage a lot in cooking but have never came across Pineapple Sage I will have to have a google…the squash look and sound delicious not sure about the vegan sausage not something I have used yet 🙂

    1. I made this, as well as stuffed zucchini, to have a quick entree for a few of my vegan friends. Most of them taste like chalk, but there are a couple that have fairly good flavor if mixed in with other things. In general, I don’t care to substitute the fake meat products in dishes that used to have meat because too often they are made with lots of additives and are seldom organic, meaning the soy is probably genetically modified. Most of the time, I substitute mushrooms or lentils or another bean and it almost always works!

  14. I grow sage but I’ve never heard of pineapple sage, I bet it has a wonderful taste. Another favorite of mine is Swiss chard, you have the best recipes!

    1. Thank you Diane! I love pineapple sage, and I would grow it even if it wasn’t an herb because of the beautiful scarlet flowers!

  15. I love delicata squash!! Beautiful recipe!

    1. Thank you so much! It’s definitely a favorite of ours.

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