This is one of the most popular recipes from my cookbook, Hungry for Harbor Country. It's a perfect gluten free Thanksgiving side dish and has helped turn a whole lotta' Brussels sprout haters into lovers—because the roasted sweet and savory flavors are down right addicting!
Preheat the oven to 400°F. Line two baking sheets with parchment paper or aluminum foil, brush with oil, and set aside.
In a large mixing bowl, mix together the brussels sprouts and squash. Drizzle with the olive oil, sprinkle the brown sugar evenly over the top, and add the chili powder, salt, pepper, and allspice (if using). Toss using a spatula or two large spoons, ensuring the vegetables are evenly coated. Add more salt and pepper to taste.
Divide the vegetable medley evenly between the two prepared baking sheets in one layer to avoid steaming. Roast in the oven for 25 to 30 minutes. Remove the baking sheets from the oven and evenly divide the cherries and pecans between them, sprinkling over the vegetables. Use a spatula to gently toss the cherries and pecans with the vegetables before returning to the oven to roast another 10 to 15 minutes, until the brussels sprouts and squash are fork tender and the edges have browned.
Fill a large serving dish with the roasted vegetable medley. If not serving immediately, keep warm until you’re ready to bestow this craveable side dish upon your guests, who are likely to start requesting that you make this for most holidays and other days.
Tips for Success
If using whole butternut squash, choose large squash with longer tops and smaller bulbs, which is where the seeds are found. It’s far easier to cut cubes from the longer solid portion of the squash.
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