5 Knockout Winter Squash Side Dishes

Squash is typically harvested in the autumn and shines in the winter months, and we have five recipes that make the perfect accompaniment to your cozy main course.

Peeling squash can be arduous, but for this delicious recipe you don’t have to. The skin of acorn squash is edible. Once cut into wedges, the squash is roasted until deeply golden brown to bring out the burnished, caramelized flavor of the vegetable. Accompanied by creamy pine nuts toasted and infused in oil, the bold flavors and textures of this dish are truly unforgettable.

Apple and squash truly sing in chorus when cooked together, thanks to their ability to bring out the sweetness in the other’s flavor profile. Cutting the butternut squash into thick wedges allows it to caramelize beautifully in the oven. It’s joined by its more delicate counterpart, the apple, in the last 8 minutes of cooking. The duo is paired with a zesty combination of minced shallot, red wine vinegar, and parsley to make a perfectly rounded-out side dish.

Don’t be fooled by the fact that this hearty dish is a salad—it packs just as much wholesome and satiating punch as any other side dish. Inspired by the famed British chef Yotam Ottolenghi, butternut squash is roasted until soft and then tossed with red onion and topped with an irresistible lemon-tahini dressing. 

To ensure that the interior of your squash remains creamy while the outside roasts into a golden-caramel shell, this recipe instructs the cook to chop it into unfussy chunks. Sweet apple is added while the squash roasts, and the dish is topped with creamy goat cheese and crunchy pepitas for a silky-smooth texture and luscious flavor.

When the bowl is this delicious, the filling is really just a bonus—and what a bonus it is. A stuffing mixture of apple, onion, and sausage that complements the creamy squash is cooked on the stovetop, while the squash itself is softened in the microwave. Then, the squash is stuffed and everything is popped under the broiler for a few minutes for some roasty notes. Simple, quick, and perfectly autumnal.