Roasted Acorn Squash, with Applesauce and Cinnamon

When we were growing up, my mother cooked dinner every night. There was always a  protein, a vegetable, and a starch, although on Sundays, when one of my grandmothers cooked dinner, the lines between the food groups were blurred by a magnificent batch of spaghetti and meatballs. Now, I am the grandmother!

Milk was the only beverage served at meals, and it was poured from an “Orange Poppy” ceramic milk pitcher. Milk bottles on the table were a big No-No. All of her serving pieces were in this pattern.

One of us kids set the table and another cleared it. There was a rhythm to the dinner hour. We ate what Mom served us. At the time, I so envied our next-door neighbors who on Monday nights got to eat TV Dinners when The Monkees came on.

Mom was a single parent who worked full-time and was a fabulous cook. I was her sous chef and worked by her side to get dinner on the table nightly. Helping with dinner was a point of pride; we were a team. While structured family meals have undergone some changes in the last fifty years, the way I prepare acorn squash remains the same. Mom knew how to prepare adult foods so children would eat them.

Serves 8


4 acorn squashes
¼ cup extra virgin olive oil
2 cups unsweetened applesauce
Cinnamon sugar (1 T sugar and 1 t ground cinnamon)
cracked pepper or garlic pepper

Preheat oven to 400º
Line two baking sheets with parchment paper.

Prepare Squash:
Cut off each end of the squash. Cut off as little as is necessary to stabilize the squash, so it stays upright.

Cut squash in half. Take a moment to admire nature’s beautiful details, and then … scoop out the seeds!

Coat the interior and top edges with EVOO.

Add one-third cup of applesauce to each squash half. Sprinkle with cinnamon sugar, followed by a little cracked pepper or garlic pepper. Place squash halves on a parchment paper-lined baking sheet.

Roast for 45- 60 minutes, until fork-tender. Serve in a pretty serving dish.

I love to eat them cold from the fridge the next day so I always make extras.

Mom and I in the kitchen. She was tiny but mighty.

Serve with:
Cooking Dinner in an Unfocused Way, or Ode to the Rice Cooker
Brooks’s Pork Tenderloin with the Most Amazing Marinade
Judy’s Mom’s Meatloaf
Mom’s Marinated and Grilled Lamb
Mom’s Apple Pie (with a cheddar streusel topping)
Mom’s Pumpkin Pie


Follow my photos of vegetables growing, backyard chickens hanging out, and dinner preparations on Instagram at JudysChickens.

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© 2014-2020 Judy Wright. All rights reserved. Photos and text may only be used with written consent.

24 thoughts on “Roasted Acorn Squash, with Applesauce and Cinnamon

  1. Oh does this bring back memories! I’ve never heard of the applesauce trick, will have to try that. On Sundays I would go home with my Grandma after church – she would have started the meal before church and Grandpa would tend it. My great Aunt would join us and we would play games while Grandma finished dinner. Table was always properly set and the good china was used and I had better use my manners. Great times!

    1. Kathy, Yes! The sauce was started by my grandmothers before they went to church on Sunday, too. Before they left for church they would turn the heat off. Dinner was served when they got back home. The rest of the day you were too full to do anything useful. And the table was beautifully set. Thanks for sharing your memories. They were good times. Smile.

  2. That squash made it into my napkin most of the time- it was the one thing I dreaded most, since until our plate was cleaned, you had to sit at the table (sometimes for hours)-I remember that milk pitcher well-finally, where is the “shake and bake” 😆

    Samuel A Culotta Jr. President, Broker – Owner Platinum Group Companies, LLC

    1. Sam!! Your post made me laugh. Lou was the king of falling asleep at the dinner table. I have a picture of him (somewhere) doing just that. Shake and Bake! I forgot all about THAT. Mom used it for chicken and thin pork chops. You are such a good rememberer. xo

  3. I have an acorn squash in my kitchen. I prepare and cook it like you do except I fill each of the centers with cranberries, (fresh or frozen) sprinkle with about 1T brown sugar, add some cinnamon and place 1T salted butter on top. Next time I’ll try yours!

  4. Hi Judy,

    Had to laugh at your latest blog post – the intro could have been written about our family. Yes, we always sat down to meals together. Dinners like yours, were a protein, veggie and starch for the most part, there were exceptions. My mother didn’t allow milk bottles on the table either, nor any condiment jars or green cans of parmesan cheese. All of that stuff was transferred into their own bowls.

    I was always envious of my friends who didn’t have to “sit down” to a meal with the family, but could eat on the fly. In fact I liked it when my dad was out of town and meals became more casual, like waffles and sausage. Better yet we got to go to Howard Johnson’s for fried clams!

    TV DINNERS!! The only time I had one of those was when my parents were going out so that was a “treat” for me. I only liked one kind – it was pork with stewed apples and I can’t remember what else.

    Ah, those shared universal memories . . .


    1. Kren, no condiment jars were allowed on our dinner table, either. Think about all the extra dishes to be washed that those bowls generated. I loved when Mom made pancakes for breakfast, too. It seemed so decadent at the time. Plus, faster cleanup. The only time I had TV Dinners was when I babysat for one family on Friday nights — that’s how I learned about Salisbury Steaks. I never ordered one in a restaurant because of my remembrance of how they tasted in those tin trays.

      Look what a great cook you turned out to be, by the way – some of that love of great cooking stuck. Thanks for writing! xo

  5. This looks great (well, not that TV dinner!), and reminds me to plant acorn squash again when it’s time to get back out to the garden!

    1. That is my favorite image, as well! I didn’t grow them. I picked up a boxful at a Mennonite farmstand in KY where we go for vegetables. They had a big sell off just before they closed in November for the winter. They last for a long time.

  6. O how I loved your story……she and I are from a different time, one which is now a lost art. I still do it for small dinners but my dinner guests say I am being “too fancy”….. hey, I love being fancy once in a while. XOXO

  7. If you are hosting Thanksgiving Day dinner what do you “make-ahead” and how do you plan your days leading up to the big day?

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