Roasted Winter Squash Two Ways (Sweet or Savory)

There’s something about making roasted winter squash that just feels like fall.

By the time the weather starts cooling down here in Wisconsin, our garden is winding down, the summer vegetables are coming to an end, and we’re bringing in the last of our winter squash.

And one of our favorite ways to enjoy it is also one of the simplest.

We cut the squash in half, scoop out the seeds, and roast it in the oven with a little butter and whatever seasonings sound good that day.

Most of the time, we make it sweet with a little brown sugar or maple syrup, butter, and a dash of salt. But sometimes we change things up and make a savory version instead.

Our favorite varieties for roasting this way are acorn and delicata squash. Both have wonderful flavor, and they’re the perfect size for an easy side dish.

Like so many of the things I cook, this isn’t really a recipe that needs exact measurements. It’s more of a simple method that you can adjust depending on what you have and what your family enjoys.

And that’s one of the things I love most about cooking from scratch.

A Simple Way to Enjoy the Fall Harvest

One of my favorite things about growing winter squash is that it gives us something fresh from the garden to enjoy long after most of our summer vegetables are finished.

Unlike zucchini and summer squash, which need to be eaten or preserved fairly quickly, properly cured and stored winter squash can last for months. Acorn and delicata have a shorter shelf life than others like butternut, so we tend to use them up first in the fall.

All that makes it such a wonderful crop to grow on the homestead.

And when you have a few beautiful acorn or delicata squash sitting on the counter, it doesn’t take much to turn them into a delicious side dish.

There’s no peeling, no complicated preparation, and no long list of ingredients.

Just cut them in half, scoop out the seeds, and let the oven do most of the work. Roasted winter squash for the win.

Our Favorite Winter Squash for Roasting

While there are many varieties of winter squash, acorn and delicata are our favorites for this recipe.

Acorn Squash

Acorn squash has a dark green, ridged skin and a beautiful golden-orange flesh.

It has a mild, slightly sweet, nutty flavor that becomes even better when roasted.

The natural hollow in each half is perfect for holding a little melted butter and maple syrup or brown sugar.

And because the squash holds its shape well during cooking, you can serve it right in the skin.

Delicata Squash

Delicata squash is another favorite around here.

It’s usually smaller and more elongated than acorn squash, with cream-colored skin and green or orange stripes.

The flesh is sweet, tender, and delicious when roasted.

One of the nice things about delicata squash is that the skin is thin and edible when cooked, so there’s no need to peel it.

Delicata also tends to cook a little faster than larger acorn squash, so keep that in mind when you’re roasting different varieties together.

Can You Use Other Winter Squash?

Absolutely!

Butternut, buttercup, and other winter squash varieties can also be roasted using a similar method.

Larger squash may need more cooking time, and some varieties have thicker skins that you probably won’t want to eat.

The important thing is to cook the squash until the flesh is tender.

You Don’t Need a Special Oven Temperature

One of the things I love about this recipe for roasted winter squash is how easily it fits into whatever else I’m making for dinner.

I rarely heat the oven to a specific temperature just for the squash.

If I’m already baking chicken, roasting meat, or cooking another side dish, I’ll simply put the squash in the oven alongside it.

Anywhere between 350°F and 400°F works well.

Of course, the cooking time will vary depending on the temperature, the size of the squash, and how tender you like it.

A smaller delicata squash might cook fairly quickly, while a large acorn squash may take quite a bit longer.

That’s why I always check the squash with a fork rather than relying strictly on the clock.

When the flesh is soft and easily pierced, it’s ready.

How to Roast Winter Squash in the Oven

This is the basic method we use whether we’re making sweet or savory squash.

Step 1: Wash and Cut the Squash

Start by washing the outside of your squash to remove any dirt.

Using a large, sharp knife and a sturdy cutting board, carefully cut the squash in half lengthwise.

Winter squash can be pretty hard, so take your time and make sure the squash is stable before cutting.

Sometimes if it seems impossible to cut, I put the whole squash in the microwave for 30 seconds or a minute to soften it up enough to slice through.

Step 2: Scoop Out the Seeds

Use a spoon to scoop out the seeds and stringy pulp from the center of each half.

You can compost the seeds and pulp, save suitable seeds for planting if you’re growing an appropriate variety, or even roast the seeds for a snack.

Our pigs always get them around here.

Step 3: Place Cut Side Down

Place the squash halves cut side down in a baking dish or on a rimmed baking sheet.

I like starting them this way because it helps trap some of the moisture and allows the squash to soften as it cooks.

If your pan tends to stick, you can lightly grease it or add a small splash of water to the baking dish. I use a silat or parchment paper if not using a glass container.

Step 4: Roast for About 30 Minutes

Place the squash in an oven heated anywhere between 350°F and 400°F.

Let it roast cut side down for approximately 30 minutes.

For smaller delicata squash, you may want to check it a little sooner.

Step 5: Flip the Squash Over

After about half an hour, carefully turn the squash halves over so the cut sides are facing up.

Be careful, as the squash and pan will be very hot.

At this point, the flesh should be beginning to soften.

Now comes the fun part: adding your favorite seasonings!

Step 6: Add Butter and Seasonings

For a sweet version, add a little butter, brown sugar and/or maple syrup, and a dash of salt to each squash half.

For a savory version, add butter or olive oil along with your favorite herbs and seasonings.

Return the squash to the oven and continue baking until the flesh is completely tender.

The butter and seasonings will melt into the squash as it finishes cooking.

Our Favorite Way: Sweet Roasted Winter Squash

This is how we make our winter squash most of the time.

There’s just something about the combination of sweet squash, melted butter, and a little maple syrup and/or brown sugar that is so delicious.

And you really don’t need much.

For each squash half, I usually add a small pat of butter, a sprinkle of brown sugar or a drizzle of maple syrup, and just a dash of salt.

Sometimes I’ll use both brown sugar and maple syrup if I’m feeling a little extra generous!

The salt might seem like a strange addition to a sweet dish, but it really helps bring out the flavor of the squash.

As the squash finishes roasting, the butter melts and combines with the sugar or syrup to create a wonderful little pool of sweetness in the center.

To serve it, we get a 1/2 of the squash on our plates. Each person can use their spoon or fork to scrape down the sides of their squash and mix it up with the sugary mixture in the middle.

It’s simple, comforting, and one of our favorite fall side dishes.

Try a Savory Version, Too!

While we usually prefer our winter squash on the sweeter side, a savory version is delicious, too.

Instead of brown sugar or maple syrup, try adding:

• Butter or olive oil
• Salt and freshly ground black pepper
• Garlic powder
• Onion powder
• Italian seasoning
• Fresh or dried thyme, rosemary, or sage

You certainly don’t need all of these at once.

I usually choose just a few seasonings that go well with whatever else we’re having for dinner.

For example, butter, salt, pepper, and a little sage are wonderful with roasted chicken or pork.

Garlic and rosemary are another delicious combination.

And if you want something really simple, just butter, salt, and pepper allow the natural flavor of the squash to shine.

How Do You Know When Winter Squash Is Done?

The easiest way to tell if your squash is finished cooking is to pierce the flesh with a fork.

If the fork slides in easily and the flesh is soft, it’s ready.

If there’s still resistance, give it a little more time.

The total cooking time can vary quite a bit.

At 350°F, larger acorn squash may take an hour or longer.

At 400°F, smaller squash may cook more quickly.

And remember, delicata squash generally cooks faster than acorn squash because it’s smaller and has thinner flesh.

Don’t worry too much about the exact time. Just cook it until it’s tender and delicious!

Easy Roasted Winter Squash (Sweet or Savory)

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Learn how to make roasted winter squash with butter, maple syrup, brown sugar, or savory herbs. An easy fall side dish using simple ingredients.

Prep Time 10 minutes

Cook Time 40 minutes

Total Time 50 minutes

Ingredients

• This is more of a cooking method than a strict recipe. Use the measurements as a starting point and adjust them according to the size of your squash and your family's tastes.
• Basic Ingredients
• 1–2 acorn or delicata squash
• Butter or olive oil
• A dash of salt
• For Sweet Roasted Squash:
• 1–2 teaspoons butter per squash half
• 1–2 teaspoons brown sugar or maple syrup per squash half, or to taste
• A dash of salt
• For Sweet Roasted Squash:
• Butter or olive oil
• Salt and freshly ground black pepper
• Garlic powder, optional
• Onion powder, optional
• Italian seasoning, rosemary, thyme, or sage, optional

Instructions

1. Preheat the oven to anywhere between 350°F and 400°F.
   
2. Wash the squash and carefully cut each one in half lengthwise.
   
3. Scoop out the seeds and stringy pulp.
   
4. Place the squash halves cut side down in a baking dish or on a rimmed baking sheet.
   
5. Roast for approximately 30 minutes, checking smaller delicata squash sooner.
   
6. Carefully flip the squash halves so the cut sides face up.
   
7. Add butter and your choice of sweet or savory seasonings.
   
8. Return the squash to the oven and continue roasting until the flesh is soft and easily pierced with a fork.
   
9. Spoon the melted butter and seasonings over the squash before serving.

Notes

Cooking time varies depending on the squash variety, size, and oven temperature.

Delicata squash usually cooks faster than acorn squash.

The skin of delicata squash is edible when cooked.

Brown sugar and maple syrup can be used separately or together.

For a savory version, try butter, salt, pepper, and sage.

Leftover roasted squash can be refrigerated in an airtight container for 3–4 days.

Enjoying the Harvest One Simple Meal at a Time

One of my favorite things about growing our own food is finding simple ways to enjoy what we’ve harvested.

Winter squash is such a wonderful example.

We plant it in the spring, watch the vines spread through the garden all summer, and harvest those beautiful squash as autumn approaches.

And then, on a cool fall evening, we can take one of those squash, cut it in half, add a little butter and seasoning, and have a delicious homemade side dish without much fuss.

That’s the kind of cooking I love.

Nothing complicated. Nothing fancy. Just good food made with simple ingredients.

Whether you prefer your winter squash sweet with maple syrup and brown sugar or savory with herbs and garlic, I hope you’ll give this easy method a try.

And don’t be afraid to experiment a little. Sometimes the best recipes are the ones we make up as we go!

Happy cooking!