Maple Walnut Roasted Delicata Squash

Autumn Roasted Delicata Squash at The Little Shop of Olive Oils

If fall had a favorite side dish, this just might be it. 🍂 Sweet, caramelized delicata squash gets roasted until golden around the edges, then topped with tart cranberries, crunchy toasted nuts and fresh herbs for a colorful dish that feels right at home on any autumn table.

For our Little Shop twist, we're bringing together two of our October favorites: Roasted Walnut Oil and Vermont Maple Dark Balsamic. The walnut oil adds a rich, toasted nuttiness while the maple balsamic brings just enough sweetness and tang to make that roasted squash absolutely irresistible.

The Perfect Cozy Fall Side Dish

Delicata squash is one of those fall ingredients we look forward to every year. It's naturally sweet and nutty, it caramelizes beautifully in the oven, and—possibly the best part—you don't even have to peel it!

This Maple Walnut Roasted Delicata Squash is simple enough for a cozy weeknight dinner but pretty enough to earn a spot on your Thanksgiving or holiday table. And those gorgeous half-moon slices make the finished dish look like you put in much more effort than you actually did. We won't tell. 😉

What Makes This Roasted Delicata Squash So Delicious?

  • Delicata squash becomes tender, sweet and beautifully caramelized in the oven.
  • Roasted Walnut Oil adds a deep, nutty richness that pairs naturally with winter squash.
  • Vermont Maple Dark Balsamic gives the dish a sweet, tangy maple finish without needing traditional maple syrup.
  • Cinnamon adds just enough warmth to make the whole dish feel extra cozy.
  • Cranberries or pomegranate add a tart pop of flavor and beautiful seasonal color.
  • Toasted nuts bring crunch and tie everything back to that wonderful roasted walnut flavor.
  • Fresh thyme or parsley adds a fresh finishing touch that balances all those rich fall flavors.

Roasted Walnut Oil + Vermont Maple Balsamic = Fall Magic

This is exactly the kind of recipe where our Roasted Walnut Oil and Vermont Maple Dark Balsamic shine together.

The Roasted Walnut Oil complements the naturally nutty flavor of delicata squash and helps those edges turn beautifully golden in the oven. Then a drizzle of Vermont Maple Dark Balsamic adds rich maple sweetness with that signature balsamic tang.

Sweet, savory, nutty and a little tangy—it's everything we want from a fall side dish.

No Peeling Required!

If you've ever wrestled with peeling a winter squash, here's some good news: delicata squash has thin, edible skin, so you can leave the peeler in the drawer. Simply cut the squash in half, scoop out the seeds and slice it into pretty half-moons.

That makes this recipe especially handy during the holidays when easy prep is always welcome.

Make It Your Own

  • Use pomegranate arils instead of dried cranberries for a fresh, jewel-toned finish.
  • Choose toasted walnuts to really emphasize the Roasted Walnut Oil.
  • Add crumbled goat cheese or feta for a creamy, savory contrast.
  • Sprinkle with red pepper flakes for a little sweet heat.
  • Add a pinch of smoked paprika or cardamom alongside the cinnamon.
  • Finish with an extra drizzle of Vermont Maple Dark Balsamic just before serving.

Can You Make Roasted Delicata Squash Ahead of Time?

You can do most of the prep ahead! Slice and seed the squash earlier in the day and keep it refrigerated until you're ready to roast. The nuts can also be toasted ahead of time.

For the best texture, we recommend roasting the squash close to serving time. Add the cranberries or pomegranate, nuts, herbs and final balsamic drizzle after roasting so everything stays colorful and fresh.

A Beautiful Side for Thanksgiving & Holiday Dinners

This recipe pairs beautifully with roast turkey, chicken, pork or ham, but it's just as delicious alongside a simple weeknight dinner. The golden squash, ruby-red fruit and fresh herbs also make it especially pretty for Thanksgiving, Friendsgiving and holiday entertaining.

And because there's no complicated sauce or fussy preparation involved, it's one of those holiday sides that looks impressive without taking over your kitchen. That's always a win in our book!

Bring the Flavors of Fall to the Table

Warm roasted squash, toasted walnut flavor, maple balsamic and all those beautiful seasonal toppings—this Maple Walnut Roasted Delicata Squash has autumn written all over it.

Grab a bottle of Roasted Walnut Oil and Vermont Maple Dark Balsamic, and give this cozy fall side a Little Shop twist. Just don't be surprised when everyone asks for seconds. 🍁

Maple Walnut Roasted Delicata Squash with Cranberries & Herbs

Servings

6-8

Prep Time

10 minutes

Cook Time

30 minutes

Calories

150

Cuisine

American

Category

Side Dishes

Sweet delicata squash is roasted with Roasted Walnut Oil and warm cinnamon until beautifully caramelized, then finished with Vermont Maple Dark Balsamic, tart cranberries, toasted nuts and fresh herbs. An easy, colorful fall side that's perfect for Thanksgiving and holiday entertaining.

Maple Walnut Roasted Delicata Squash with Cranberries & Herbs

Ingredients

  • 2–3 medium delicata squashes, halved, seeded and sliced into ½-inch half-moons
  • 2 tablespoons Roasted Walnut Oil
  • 1–2 tablespoons Vermont Maple Dark Balsamic, plus more for finishing if desired
  • ½ teaspoon ground cinnamon
  • ½ teaspoon kosher salt
  • ¼ teaspoon freshly ground black pepper
  • ⅓ cup dried cranberries or pomegranate arils
  • ⅓ cup toasted walnuts, pecans or pepitas
  • Fresh thyme or parsley leaves, for garnish
  • Red pepper flakes, optional

Directions

  1. Preheat oven to 400°F. Line a baking sheet with parchment paper or lightly grease the pan.

  2. Halve the delicata squash, scoop out the seeds and slice into ½-inch half-moons. There's no need to peel the squash.

  3. In a large bowl, combine the Roasted Walnut Oil, cinnamon, salt and pepper. Add the squash and toss until evenly coated.

  4. Arrange the squash in a single layer on the prepared baking sheet, leaving a little room between the pieces so they can caramelize.

  5. Roast for 25–30 minutes, flipping once halfway through, until tender and beautifully golden around the edges.

  6. Transfer the warm roasted squash to a serving platter and drizzle with 1–2 tablespoons Vermont Maple Dark Balsamic.

  7. Scatter the dried cranberries or pomegranate arils and toasted nuts over the squash. Garnish with fresh thyme or parsley and red pepper flakes, if desired.

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