Acorn Squash Stuffed with Beef

Along with the pumpkins, October rings in a great variety of squash. Acorn squash is a fun one to work with, providing you with a rich, orange-colored, naturally sweet bowl that is ideal for stuffing with something savory. You’ll find a really wide range of interesting fillings out there–apples, nuts, rice, meats–all sorts of things. No matter what the filling though, they all have one thing in common: they showcase the tender texture and the sweetness of the squash.

Acorn squash stuffed with beef

In this case, I’ve stuffed my squash with a ground beef mixture which has Mexican flavors akin to a milder mole sauce that is tilted less towards spicy and more towards sweet and savory so as to enhance the sweetness of the squash. There’s a lot of savory spices and a small amount of heat, but a lot of the major players in this mixture work towards having a fuller profile of sweetness: dark molasses, balsalmic vinegar, golden raisins, bittersweet chocolate, honey, lime, and brown sugar.

  • 1-1.5 lbs ground beef
  • 2 Acorn squash
  • Extra virgin olive oil
  • Honey
  • Dark brown sugar
  • 1 red pepper
  • 6 cloves of garlic
  • 5 scallions
  • 1/4 cup cilantro leaves
  • 1/4 cup flat-leaf Italian parsely leaves
  • 1/4 cup golden raisins
  • 1/8 cup bittersweet chocolate
  • 1/4 cup dark molasses
  • 1/4 cup tomato sauce
  • 2 Tbsp balsalmic vinegar
  • juice of 1 lime
  • 1 tsp dried oregano
  • 1-2 tsp ground cinammon
  • 1 tsp ground cumin
  • 1/2 tsp ground nutmeg
  • 1/2 tsp ground pepper
  • 1/2 tsp cayenne
  • 1/2 tsp chipotle

If you’ve never worked with acorn squash before, go for one which is firm and has a deep, rich green skin (some bright orange patches are fine!).

Open and clean the acorn squash

With a sturdy knife, carefully halve your squash from top to bottom, take in the aroma, and scoop out the seeds and stringy stuff. Also worth noting, you can hang on to the seeds and roast them, just like you would pumpkin seeds if you’re into that.

Fill each squash with honey and oil

Preheat your oven to 400? F. Fill a baking pan with roughly half an inch of warm/hot water and place your squash halves in this, open side up. The water is there to both keep the squash moist and to prevent sticking. Now fill each squash cavity roughly half way up with a mixture of extra virgin olive oil, honey, and a crumble of brown sugar. While squash is inherently sweet, we want to help bring those sugars to the forefront, so while the squash are cooking, they’ll have this sweet mixture seeping down into them. A few fork pricks in your squash will get better penetration.

So now transfer your squash baking pan to the oven. You want them cooking until you can somewhat easily prick them with a fork, which for me, took somewhere around 45 minutes (this will vary by squash). You don’t want to leave them in terribly long though as you will be baking them again in a little bit, so keep your eye on them.

Brown the beef Dice the veggies

While that’s baking, let’s prepare the filling. Dice up your garlic and pepper somewhat finely. Start browning your beef over medium heat and as the beef looks almost totally browned, add in your garlic and pepper so as to fry them in some of the grease. Keep tossing the mixture so nothing gets burnt, and also, dice up your remaining fresh items (cilantro, parsely, and scallions). Once the veggies seem done frying (~5 minutes), toss the herbs and the raisins in.

Simmer the beef with everything else

Finally, incoroporate all of the remaining ingredients into the beef mixture and just keep it moving. The chocolate should melt down, the molasses will mobilize, and combined with your balsalmic and tomato, your beef mixture will quickly take on a darker tone with a really complex sweetness to it. Consider lowering the heat, if not completely turning it off–you don’t want this mixture to start sticking nor do you necessarily want to totally finish cooking. Preparing the filling can go pretty quickly relative to baking the squash, so you don’t want to leave it over heat for too long while you wait for the squash to finish. Otherwise, the final step (baking in the oven) will dry out your meat. Its ok for the meat to still look a little “wet” at this point with everything we recently added.

Spoon the beef into the baked squash

So once your squash are done baking, drop the oven temperature down to 350?F and remove them from the oven. Carefully scoop out the honey/oil mixture that’s been sitting in each squash reservoir and set this aside in a cup. Now, scoop in your beef mixture, filling each squash equally, probably just a little over capacity. Finally, drizzle your honey/oil mixture back over the beef and into the squash again.

Completed stuffed squash

Return your baking pan to the oven for 25-30 minutes more. Once they’re done, you should have a juicy, tender squash with your name on it. I find a half of a squash to be the perfect sized serving for one.


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