Vanilla-Maple Grilled Acorn Squash (adapted from Grill Every Day, 2007)

In my neck of the woods acorn squash is a winter vegetable, and winter’s not a pleasant time to grill.  But after reading Diane Morgan’s Grill Every Day (2007) I was determined to take her at her word.  Ms. Morgan is a Pacific Northwesterner like me – if she could do it, so could I.   And I’m glad I did – acorn squash grills up brilliantly and the sweet maple glaze that Ms. Morgan recommends is stellar.  Think smoky candied yams with a caramel char – it elevates a vegetable that I frankly find otherwise inedible into something worth celebrating.

This is fantastic as a vegetarian main course, but for a carnivore like me this recipe presents some logistical challenges.  Acorn squash takes some time to soften, meaning that you need a long cook over indirect heat.  If you’re using charcoal this typically means pushing the coals to the sides and leaving an open spot in the center.  If you’re using gas it means turning off a couple of burners.  Either way it means that you’re working with less cooking area that you’d normally be accustomed to, and if you’ve got a standard 22″ round grill like I’ve got there just won’t be enough room for all the acorn squash.   There also won’t be room to grill up the hearty pork or poultry main that this dish demands.

So when I make this at home I cheat.  I prep the grill for a medium-hot sear and pre-cook the squash in the oven.  Once the squash is soft I lather on the glaze and give it a nice hot sear, the same way I would a good steak or pork chop.  I’m sure that I’m sacrificing some smoky goodness in the process, but if I have to choose between that and a tepid sear on the main course it’s worth the tradeoff.   I’ve included instructions for both the traditional grilling and “cheating with the oven” method below.

I’ve made one important change to Ms. Morgan’s original recipe.  The original recipe calls for a good quality bourbon, and I’ve got a house full of teetotalers.  I’ll cook with wine from time to time, but I’ll go through a bottle or two in a single recipe.  I’ve only got a handful of recipes that call for bourbon. It would take me five or six years to work through a bottle, and I’ve got better things to do with my cupboard space.  Instead of bourbon I’ll use a tablespoon of a good quality vanilla.  It’s not quite the same flavor profile, but it still pairs well with the maple syrup.

Vanilla-Maple Grilled Acorn Squash is sweet and rich and delicious.  It’s not quite dessert-quality sweet like your average marshmallow-and-yams, but it needs a strong salty counterbalance.   When I cooked this last for my family I paired it with an Espresso-Cardamom Rubbed Pork Roast, inspired by the same cookbook, but a thick slice of ham would have worked well also.  The thought of serving this with beef makes me a little bit uneasy, but fresh roast turkey, a sage-scented poultry sausage, or even a rotisserie chicken would match well.   I have a hard time deciding whether squash is a starch or a vegetable so I usually call it neither and serve a green salad and a starch alongside.   Enjoy!

Vanilla-Maple Grilled Acorn Squash (adapted from Grill Every Day, 2007)

  • Preparation: 10 min
  • Cooking: 30 min
  • Ready in: 40 min
  • For: 8 side dish servings
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  1. Prepare a grill with a "hot side" and a "cold side". On a charcoal grill this usually means pushing all of the coals to one side, or covering half of the coals to facilitate indirect cooking. On a gas grill this means preheating the grill and then turning off one of the burners. If all of this seems like too much trouble, or you are grilling other food besides the squash, prepare a medium-hot grill and preheat your oven to 350º F.
  2. Cut acorn squash in squash and scoop out the innards. Slice into wedges as you would a cantaloupe, 8-12 wedges per squash depending on their size. Trim away any woody bits near the stem. Lay on a baking tray and then set aside.
  3. Melt ¼ cup of butter in the microwave or a small saucepan. Ladle over the top of the squash, turning the squash as needed and brushing to ensure that all surfaces are coated. Sprinkle with salt and pepper.
  4. Place on the "cold side" of the grill, cover and cook with indirect heat for 20-25 minutes until skin is starting to peel away and squash is tender. If you're using the oven, bake in a 350º F oven for 15-20 minutes.
  5. While the squash is cooking, melt the remaining butter and whisk in the remaining ingredients.
  6. Brush the squash on both sides with the butter/syrup mixture. Place slices on the "hot side" of the grill and cook over direct heat for 2-3 minutes per side, until you have pronounced grill marks and the glaze is nicely caramelized. Continue brushing with glaze as desired while grilling, being careful not to burn.

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