This Honey Balsamic Roasted Acorn Squash and Brussels Sprouts dish is one of those late-autumn sides that feels both cozy and a little celebratory. I first put this together on a chilly November evening when I had a medium acorn squash and a bag of small Brussels sprouts left from a farmer's market run. The combination of honey and balsamic adds a glossy, balanced glaze that caramelizes just enough on the edges while the cranberries add bright bursts of tartness. It quickly moved from an experiment to a regular on our weeknight rotation and then to the holiday table when friends came by.

The textures are part of what make this dish stand out. The acorn squash slices roast to tender, melt-in-your-mouth pieces with crisped edges, while the Brussels sprouts develop a sweet, nutty char. The cranberries remain pleasantly chewy and tangy. I like that it can be plated alongside roasted meats, grain bowls, or simply served with crusty bread. It is forgiving, forgiving in timing and technique, and accessible in ingredients so it is a perfect choice when you want something seasonal and impressive without an elaborate process.

Ingredients

• Acorn squash: One medium acorn squash, roughly 1.5 to 2 pounds. Look for a firm squash without soft spots and with a deep green skin. The skin crisps when roasted and is edible, so no need to peel.
• Brussels sprouts: Twelve small Brussels sprouts, about 10 to 12 ounces. Choose compact, bright green sprouts; trim the stem ends and remove any loose outer leaves to help them caramelize evenly.
• Extra virgin olive oil: Two tablespoons. A good quality extra virgin adds aroma and helps the glaze adhere and crisp the edges.
• Honey: Two tablespoons of a mild, runny honey. Local wildflower or clover honey works well for balanced sweetness.
• Balsamic vinegar: One tablespoon, preferably a good-quality aged balsamic for depth. It provides a tangy counterpoint that turns syrupy as it roasts.
• Fresh cranberries: Half cup of fresh cranberries. These add bright tartness and a pop of color; frozen can be used but fresh keeps a better texture.
• Salt and pepper: Kosher salt and freshly ground black pepper to taste. Start with about 1/2 teaspoon salt and 1/4 teaspoon pepper and adjust at the end.

Instructions

Preheat the oven: Set the oven to 375 degrees Fahrenheit and position a rack in the center. A moderate oven allows the squash to soften without burning the glaze; 375 F produces tender centers and nicely caramelized edges in 15 to 20 minutes. Prepare the squash: Wash the squash and slice off the stem and tip. Cut in half from stem to tip and scoop out the seeds with a spoon. Place the halves cut side down on a cutting board for stability and slice into 1/2 to 3/4 inch wide crescents. Keeping the skin on helps the slices hold together while roasting and adds texture when crisped. Trim the sprouts: Trim the stem ends of the Brussels sprouts and halve any larger ones so pieces are roughly the same size as the squash slices. Even sizing ensures even cooking and consistent caramelization. Make the glaze: In a large bowl whisk together 2 tablespoons extra virgin olive oil, 2 tablespoons honey, and 1 tablespoon balsamic vinegar. Whisk until thinly emulsified. The oil helps the honey and vinegar coat the vegetables and encourages browning during roasting. Toss and arrange: Toss the squash slices and Brussels sprouts in the bowl to fully coat them with the glaze. Spread them in a single layer on a rimmed baking sheet; crowding can cause steaming instead of roasting so use two sheets if needed. Roast: Roast for 15 to 20 minutes, turning once halfway through, until squash is fork tender and edges are caramelized. Add the cranberries for the last five minutes of roasting so they heat through but retain chew and brightness. Timing varies slightly with oven and thickness of slices; look for golden edges and a tender center. Finish and serve: Remove from oven, sprinkle with salt and freshly ground pepper to taste, toss gently, and serve immediately. The dish is best warm when the glaze is glossy and the cranberries are still slightly chewy.

Storage Tips

Cool leftovers to room temperature for no more than two hours, then store in an airtight container in the refrigerator for up to three days. To freeze, spread cooled vegetables on a baking sheet in a single layer, freeze until firm, then transfer to a freezer-safe bag for up to three months. Reheat thawed portions in a 350 F oven for 10 to 12 minutes to regain crisp edges. Avoid microwaving from frozen as it can make the squash mushy.

Ingredient Substitutions

Maple syrup can replace honey one-for-one for a slightly earthier sweetness and to make the dish vegan. If you do this, select a good-quality aged balsamic for depth. Swap red or golden beets for squash in a pinch, but increase roasting time. Dried cranberries may be used if fresh are not available; soak dried berries in warm water for 10 minutes to plump them before adding in the final minutes of roasting.

Serving Suggestions

Serve warm as a side to roasted turkey, pork tenderloin, or grilled chicken. For a vegetarian plate, spoon over warm farro or quinoa and top with toasted pepitas and a squeeze of lemon. Garnish with chopped fresh parsley or a few crumbles of goat cheese if you tolerate dairy. This also pairs nicely with a simple arugula salad dressed with lemon and olive oil to cut the sweetness.

Cultural Background

Roasting winter squash and brassica vegetables is a classic technique in American fall cooking that highlights seasonal produce. Balsamic and honey glazes are inspired by Mediterranean flavor combinations that balance sweet and tangy elements. This dish is a fusion of straightforward American roasting tradition with the sweet-tang pairing common in European cuisine.

Seasonal Adaptations

In winter, use roasted chestnuts and dried cherries for a rich holiday version. In early fall, add sliced apples with the cranberries for a fruity note. For spring or summer, substitute with roasted zucchini and halved cherry tomatoes and finish with a light balsamic reduction rather than the honey glaze.

Meal Prep Tips

Trim and slice the squash and sprouts up to 24 hours ahead and store separately in airtight containers. Make the glaze and keep it at room temperature; toss just before roasting to prevent the honey from sticking. Dividing into meal-size portions and using shallow containers helps foods cool quickly and reheat evenly. This makes weekday dinners effortless and great for packed lunches.

Sharing this dish feels like sharing a small season in a bowl. It is simple, adaptable, and has earned a place at our table for both ordinary meals and special occasions. Try it once and you will likely find yourself returning to the honey and balsamic combo as a fast way to transform humble vegetables into something just a little bit magical.