Chipotle Brown Sugar Baked Acorn Squash

Updated 4.17.2020.

Here’s what I said about this dish back in 2014:

With a snow storm hitting Portland hard this weekend, I was mostly stuck in doors. This gave me a lot of time to clean, organize, watch the Olympics and, of course, cook.

I’ve had an acorn squash and some sugar pumpkins sitting on my countertop for a few months now. I noticed today that my acorn squash was starting to turn a bit orange. Perhaps over-ripening or going bad. Not wanting to waste the squash or the pumpkins, I decided to spend my afternoon roasting.

This recipe is inspired by one found at Simply Recipes, one of my go-to blogs when I’m looking for classic recipe.

I’m not sure how thrilled I am over the combination of chipotle and brown sugar. I thought it would be a good combo (spicy and sweet) but it just wasn’t all that jazzy to me. I ended up having to add a lot of salt to bring out the flavor. Or maybe my acorn squash is over-ripened/gone bad. The good thing about experimenting with an acorn squash is they are small so if you don’t like what you make and don’t end up eating it, you haven’t wasted a bunch of food. I’m betting the classic Simply Recipes version is a winner.

In recreating this dish in 2020, I thought long and hard about whether or not I wanted to try to recreate a dish that I wasn’t too thrilled about in 2014. And I decided I didn’t. That being said, I still wanted to add a little bit of spice to the dish so instead of adding some chipotle pepper to it, I put the smallest dollop of Sriracha sauce into each half before baking.


  • 1 acorn squash
  • 1 T. Butter
  • 1 T. Brown Sugar
  • Chipotle Pepper or Sriracha Sauce (optional)
  • Salt and pepper


  1. Preheat oven to 400°F.
  2. Using a large chef’s knife, cut the acorn squash in half. Use a spoon to scoop out the seeds and the stringy guts in the center of each half.
  3. Score the insides of each half several times with a sharp knife. Place each half in a baking pan, cut side up. Add about a ¼ inch of water to the bottom of the baking pan so that the skins don’t burn and the squash doesn’t get dried out.
  4. Coat the inside of each half with the butter. Add brown sugar to the inside of each half and chipotle pepper or Sriracha sauce if using. Sprinkle with a little bit of salt in each half.
  5. Bake in the oven for 1 hour to 1 hour 15 minutes, until the squash is very soft and the tops are browned. Be careful not to undercook. I “basted” my halves with the brown sugar/butter mixture while baking.
  6. Remove from oven and let cool slightly before serving. Spoon the meat of the squash and the sauce into a bowl and mash. Add salt and pepper to taste. Serves two to four, depending on the size and appetites.

Recipe rating: 



  1. I would think the chipotle and the brown sugar would be a nice combination. I suppose you don’t really know until the dish is finished, which is sort of the fun of experimenting in the kitchen. And, as you mentioned at least you didn’t waste a lot of food and a lot of expensive, hard to find ingredients.


    1. Thanks, Allison. I was a bit disappointed. When I “dreamt up” the combination I did a web search and found a butternut squash post using the flavor combination and they raved about. Maybe I can chalk it up to an over-ripened squash!


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