
Maple Roasted Delicata Squash with Cranberries brings together the honeyed softness of squash and the jewel-bright tang of cranberries for a side dish bursting with fall flavor. I reach for this recipe every time autumn squash hits the markets because the colors alone feel like a centerpiece, plus the hands-off roasting makes it so easy.
I first tested this for Thanksgiving but now it shows up at Sunday dinners and even weeknight meals because it checks every box for cozy and impressive.
Ingredients
- Delicata squash: choose firm, heavy squash with bright coloring and no soft spots, its edible skin means no peeling so look for nice clean skins
- Pure maple syrup: the real stuff brings rich flavor and sticky caramelization, thinner syrupy blends just do not give the same effect
- Fresh cranberries: look for glossy berries that feel plump not mushy, frozen work too just do not thaw first or they get mushy
- Olive oil: helps every piece brown evenly and crisps the edges, a good extra virgin makes a difference
- Sea salt: brightens and balances out both the sweet and tart
- Ground cinnamon: brings warmth and a little holiday spice, use Vietnamese cinnamon for best aroma if you can
- Black pepper: just a touch gives the dish a subtle heat and rounds out the sweet maple and tart cranberry flavors
Instructions
- Prep the Squash:
- Slice both ends off each delicata squash. Cut in half lengthwise and scoop out the seeds with a spoon. Slice into half-inch thick moons. Leave the skin intact, it softens in the oven and adds color.
- Mix the Glaze:
- In a large bowl, whisk together maple syrup, olive oil, cinnamon, sea salt, and black pepper. Make sure the mixture looks glossy and well combined so every piece gets coated.
- Toss and Arrange:
- Add delicata squash moons to the bowl and toss thoroughly until each piece is slick and shiny. Spread the squash in a single layer on a rimmed baking sheet lined with parchment for easy cleanup. Sprinkle fresh cranberries over and nestle some between the squash pieces so they roast evenly.
- Roast to Perfection:
- Slide the pan into a hot oven preheated to four hundred twenty five degrees. Roast for twenty minutes then flip each squash piece with a spatula. Roast ten to fifteen minutes longer until the squash is golden with deep caramel edges and the cranberries are slightly broken and glossy.
- Finish and Serve:
- Let the squash rest for five minutes on the pan so the maple glaze thickens as it cools. Serve right from the platter for a beautiful presentation. Leftovers reheat well in the oven or even on a skillet.

My all-time favorite part is how the tart cranberries mellow right into sticky pools of maple and squash. My family loves crowding around the kitchen island to sneak the most caramelized pieces off the pan.
Storage Tips
After cooling completely transfer leftovers to an airtight container. They stay fresh three to four days in the fridge. For longer storage spread cooled squash and cranberries on a baking sheet and freeze until solid then transfer to freezer bags. The squash reheats best uncovered in a hot oven or under a broiler to revive its crispy edges.
Ingredient Substitutions
No delicata squash Go for acorn or kabocha which have equally sweet flavor and edible skins. You can also swap out maple syrup for honey for a slightly different floral depth. If you only have dried cranberries use a small handful but reduce the maple syrup slightly since dried fruit is sweeter.
Serving Suggestions
I love piling these alongside roasted chicken pork or turkey or as part of a simple grain bowl with farro and spicy greens. They are right at home on holiday spreads but also taste amazing tucked into leftover sandwiches with a smear of cream cheese. Add feta crumbles or toasted pepitas for a savory twist.
Cultural and Historical Context
Delicata squash has been grown in North America since the nineteenth century and is prized for its thin edible skin and naturally sweet flesh. This modern version borrows maple flavors from traditional New England cookery and pairs them with cranberries which have deep roots in Native American and colonial cuisine. The simple roasting technique honors how these ingredients have long brought color and nutrition to fall meals.
Seasonal Adaptations
Swap in butternut squash or sweet potatoes when delicata is out of season. Scatter a few sprigs of fresh thyme or rosemary for extra fall fragrance. Try adding a pinch of cayenne or smoked paprika for warmth.
Success Stories
After my neighbor brought this to a potluck it quickly became the talk of the party, nobody guessed it was so simple. I started making it at Thanksgiving and now friends request the recipe every year. It is always first to disappear from the buffet and the kids love sneaking the slightly crispy squash chips when nobody is looking.
Freezer Meal Conversion
Roast a double batch and freeze half in single layers on a parchment-lined tray. Once solid bag up for easy side dishes all winter. For serving let thaw briefly and crisp in a hot oven. This works especially well for weeknight speed or vegetarian lunch bowls.

This dish is the taste of autumn and a showstopper every time. Make it part of your fall celebrations, or just for a weeknight when you need color and comfort on the table.
Recipe Help & FAQs
- → How should I prepare delicata squash?
Slice the delicata squash in half lengthwise, remove seeds, and cut into half-moon shapes with the skin on for tender texture.
- → Can I use frozen cranberries for this dish?
Frozen cranberries work well; add them directly without thawing for even roasting alongside the squash.
- → What herbs pair best with maple-roasted squash?
Fresh thyme and rosemary provide savory notes that complement the sweet maple glaze and tart cranberries beautifully.
- → How do I know when the squash is roasted perfectly?
The squash should be golden brown at the edges and fork-tender, usually after 25-30 minutes at 400°F.
- → Can I make this dish ahead of time?
Yes, roast the squash and cranberries in advance and reheat before serving. Garnish with fresh herbs last for bright flavor.