Simple Roasted Cinnamon Butternut Squash – This easy cinnamon squash side-dish is as at home on your weeknight dinner table as it is a holiday feast. Allergy-free, paleo, and vegan friendly!

Front view of cinnamon roasted butternut squash in a white bowl

As we move into fall and winter, I’m always looking for easy side dishes to add to our regular mix. In the summer, I usually rely on the abundance of fresh fruit and keep things light with lots of salads to go with lighter main dishes that work well in hot weather.

In the cooler months, as our meals get warmer and heartier, I’m always looking for yummy, easy side dishes that work well for weeknights, but also (especially!) I’m looking for healthy holiday side dishes I can serve for company, add to a Thanksgiving spread, or enjoy for Christmas.

This simple cinnamon roasted butternut squash has been one of our favorites for the last 4-5 years. It only takes 5 ingredients and doesn’t require a lot of fuss to taste amazing. (WIN!)

Butternut squash is one of those gorgeous orange veggies that plays nicely with savory flavors (like in this Autumn Squash Soup or Wild Rice Pilaf), but also goes with sweet flavors, like our Caramelized Brown Butter Squash or this Roasted Cinnamon Squash recipe.

In this recipe, the combination of maple syrup and cinnamon makes the whole house smell like cinnamon rolls (no joke!) and the flavor is gorgeous, thanks to the caramelization process. I always have a hard time not eating it all before it gets to the table!

Here’s all you need to get started…

Overhead view of cinnamon roasted butternut squash in a white bowl

Ingredients For This Easy Cinnamon Butternut Squash Recipe:

Butternut Squash. The first and most important ingredient is butternut squash! (Check out the FAQ below for tips on choosing a good squash, how to dice squash, and more!)
Olive Oil, Ghee, Butter, or Vegan Butter. I almost always make our Roasted Cinnamon Butternut Squash with olive oil, but you can absolutely use melted ghee, butter, or vegan butter.
Pure Maple Syrup. Next up is pure maple syrup. This little bit of sweetness plays up the natural sweetness of butternut squash and helps it caramelize during roasting.
Cinnamon. Then, you’ll add cinnamon. I love how this makes the squash taste and how it makes the house smell while it cooks. (The aroma is like cinnamon rolls!)
Salt. Last, but not least is some salt. This will help balance the flavors so they don’t run too sweet or too flat. Don’t skip it!

Small Business Shout-Out: Queen Creek Olive Mill

Our favorite olive oil comes from Queen Creek Olive Mill. Owned by the NICEST family who’s committed to responsible farming practices, the mill makes some of the best olive oil I’ve ever tasted. Their award-winning Balanced olive oil is my go-to for everyday cooking, but you can also use their Rosemary olive oil for a yummy flavor twist.

Overhead view of ingredients for roasted cinnamon butternut squash in a mixing bowl

Overhead view of butternut squash cubes coated with cinnamon, syrup, and olive oil

How To Make Roasted Cinnamon Butternut Squash Step-By-Step:

Preheat The Oven & Prep Your Pan. Preheat the oven to 400 degrees F. and set out a baking sheet to roast your squash.
Dice Your Squash (If You Haven’t Already). I follow this method for peeling & dicing squash.
Season & Mix The Squash. In a large bowl, mix together squash, olive oil, syrup, cinnamon, and a generous pinch of salt. Stir to combine well.
Spread Out On A Baking Sheet. Transfer the cinnamon squash and any remaining olive oil/seasonings out onto a baking sheet. Spread the squash out or shake the pan to evenly distribute the squash. (You don’t want it too tightly packed together so the air can circulate freely)
Roast, Stirring Every 10-15 Minutes. Pop the pan in the oven and roast the cinnamon butternut squash at 375 degrees F. for 35-45 minutes, or until cooked through and starting to caramelize. For even browning, stir squash every 10-15 minutes.
Enjoy! Now, that the squash is golden and roasted, the biggest challenge is not to eat it all yourself!

FAQ + Tips For The Best Cinnamon Squash Every Time.

How To Cut Butternut Squash. If you’ve never done it before, peeling and cutting a butternut squash can feel surprisingly intimidating. I promise it’s easier than it seems! This method is my favorite to peel and cut butternut squash for this roasted cinnamon squash recipe. Use a sharp knife to cut the skin away from the sides of the butternut squash, then follow these steps to cut the “neck” of the squash away from the base, then seed and dice it into cubes. (Microwaving the whole squash 30-60 seconds before cutting into it can make this a bit easier!)

Pro Tip! For The Best Texture, Set A Timer & Flip Every 10-15 Minutes. For even golden browning (and to prevent any scorching or burning), I recommend setting a timer and flipping the squash every 10-15 minutes for best results. This will give you that gorgeous caramelized outer layer, a tender interior, and even coloring.

How Many Cups Of Squash Are In a Pound? There are all sorts of ranges for this, but in general, I find that a 3 lb. squash (weighed whole, without peeling/seeding) will give me roughly 6-8 cups of diced squash. That equates to 2 to 2 2/3 cups of diced squash per pound.

How To Choose A Butternut Squash. Not sure how to pick a good squash at the store or market? Try these 5 tips for choosing winter squash! My favorite tips are to look for even coloring (no bruised/soft spots), and one that feels heavy for its size (which indicates it’s not dried out).

How To Use Leftover Roasted Squash. The easiest way to enjoy leftover roasted cinnamon butternut squash is to just re-heat it in the microwave or in the oven for a few minutes, but I also love tossing leftover roasted squash into quinoa salads like this one, or adding them to fully-loaded leafy green salads like our Fall Cobb Salad. (It’s delicious!)

How To Make Butternut Squash Last (And Last And Last). Butternut squash is a hardy vegetable and lasts weeks and weeks, but you can really extend the shelf life of an uncut butternut squash by following the butternut squash storage tips in this post From Cassie at Growfully.

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