Smaller holiday gatherings can still be special without the heavy lift of making a huge spread of food or having a bazillion dishes on the table. During the Covid years, my husband and I learned that combining favorite Thanksgiving foods into fewer dishes was a good way to satisfy all our cravings for tradition when it was only the two of us at the table.

I got the idea for this dish only a couple of years ago, and it features two of our favorite veggies, Brussels sprouts and winter squash. There’s a scatter of crispy bacon in there, too, and a luscious cranberry-maple dressing that makes it super addictive. For me, one of the requirements for Thanksgiving food is visual appeal, and this tasty side certainly has that covered, too.

There’s nothing difficult about this autumn recipe, but it is best served immediately after cooking, so get ahead of the game by making the dressing and prepping the veggies early so that putting it together at dinner time is a snap. Here we go!

The basics of roasting Brussels sprouts

Choose Brussels sprouts that are large, if possible, as they shrink considerably during roasting. They should have a fresh appearance, with tightly formed leaves. Ideally, the sprouts should all be about the same size so that they roast evenly.

We follow two key principles for perfectly roasted Brussels sprouts, and the first is removing all excess moisture. You’ll rinse them, of course, and then trim off the brown ends and halve them top to bottom. Spread the sprouts out onto a clean kitchen towel, and then roll it up and place it in a large bowl in the fridge for a couple of hours or up to one day, and bring them back to room temperature before proceeding with the roasting stage. 

The second principle for roasting any vegetable, including Brussels sprouts, is to toss them lightly with olive oil—I like to do this in a large zip-top bag— and then roast them at a high temperature so that good caramelization can take place before the veggies have a chance to turn soft or soggy. An ideal temperature is 425° F, so crank up the oven right after you take the turkey out. 

And now, the rest of the recipe

The rest of this dish is easy peasy, with sautéed onions and bacon and roasted slices of tender delicata squash. This variety of winter squash is so easy and doesn’t require peeling, because the skin is soft and edible after cooking. Go ahead and prep the squash ahead, as with the sprouts, and let them rest at room temp for a bit before you toss them in oil for roasting.

You will roast the squash at the same time as the sprouts, but not together on the same pan. They each need some breathing room for proper roasting, and then the two are layered and and drizzled with the cranberry-maple dressing when you’re ready to serve.

Ooh, this autumn dressing! 😋

This tart and sweet dressing would be delicious on any roasted autumn vegetable or even a green salad, and if you make vinaigrettes at home, you already know how easy it is to whisk a few simple ingredients together to create an emulsion. If you prefer, you could choose any store bought vinaigrette with flavors that say“autumn” to you. Avoid oil-free dressings, as their moisture content would wreck the crispy edges of the roasted sprouts.

As with most roasted vegetables, this dish is best served right away, so make it one of the last things you do while the turkey is resting under foil. If you choose to make the entire thing ahead, it will still have terrific flavor, but it will lose the satisfying crispy texture after reheating.

Just one more thing. If you omit the bacon, this dish is entirely vegan. 😊 Enjoy!

Roasted Brussels Sprouts with Delicata & Cranberry-Maple Dressing

• Servings: About 8
• Prep Time: 20 minutes
• Cook Time: 20 minutes
• Difficulty: Average
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Ingredients

• 1 1/2 pounds Brussels sprouts, trimmed and halved
• 1 medium delicata squash, seeded and cut into 1/2-inch slices
• 2 Tbsp. extra virgin olive oil, divided (you’ll use some to roast each vegetable)
• Salt and pepper to taste
• 2 slices bacon, cut into 1-inch pieces
• 1/2 medium onion, cut lengthwise into crescents
• Cranberry-maple vinaigrette (recipe below)

Notes: All components of this dish may be done one day in advance, but for best texture and flavor, suspend roasting the vegetables and assembling the dish until just before dinner.

Directions

1. Rinse and gently toss fresh Brussels sprouts in a colander under running water. Trim off brown ends and cut the sprouts in half lengthwise, discarding any damaged or discolored leaves. Spread the sprouts out onto a clean kitchen towel, and then roll it up and place it in a large bowl in the fridge for a couple of hours or up to one day. Let them sit a room temperature for an hour or so before roasting.
2. Heat a heavy skillet over medium heat. Cook bacon and onions together until bacon is just crispy and onions are somewhat tender and browned. Remove from heat and set aside.
3. Preheat oven to 425° F, with one rack just above center and the other just below. Line two baking sheets with parchment paper.
4. Transfer the sprouts to a large bowl or zip-top bag and drizzle with a tablespoon of olive oil. Toss to coat, and arrange them, cut side down, on one of the baking sheets. Sprinkle with kosher salt and give them a few twists of freshly ground pepper.
5. Toss squash slices in another tablespoon of oil and arrange slices on the other baking sheet. Resist the temptation to roast the squash and sprouts together, as they both need a little breathing room so that they don’t trap steam and turn mushy.
6. Slide both baking sheets into the oven to roast for about 20 minutes, with sprouts on the top rack and squash on the lower one. At the halfway mark, turn squash pieces over and swap the pan positions.
7. When you see plenty of roasted edges on the sprouts, remove both pans from the oven. Turn over all the sprouts to prevent steam getting trapped between the leaves. Arrange the squash slices over the sprouts and scatter the bacon and onions over the whole thing. Drizzle with the vinaigrette, but be careful not to drown them. You will have some dressing left over. Transfer to a serving bowl and enjoy!

This cranberry-maple dressing is a winner all by itself! Note that this recipe makes more dressing than you will need for the Brussels sprouts and delicata dish; enjoy the rest on a mixed greens salad with apples and candied pecans!

Ingredients

• 2 Tbsp. white wine vinegar
• 2 Tbsp. real maple syrup
• 1 Tbsp. cranberry juice
• 1 tsp. Dijon mustard
• Kosher salt and freshly ground black pepper to taste
• 4 Tbsp. extra virgin olive oil

Directions

Whisk together vinegar, syrup, cranberry juice and Dijon mustard. Season with salt and pepper to taste. Drizzle in olive oil, whisking constantly to create an emulsion.