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Fall Squash Combo Favorite

Karen D
Posted by Karen D on Oct 30, 2019


Once Fall weather starts to hit, I start thinking about all those cooler-weather dishes that make me feel so warm and comfy! At the top of my list is roasted delicata squash, with butternut squash running a close second. A few years ago I decided to put them together in one dish to see how the flavors blended together. I added a couple of other ingredients and some warm spices and before I knew it, this became my go-to Fall side dish to enjoy. As an added bonus, this dish is completely vegan, which is especially perfect over the holidays when you don’t always know your guest’s preferences!

fall squash ingredients

Many are familiar with butternut squash, but not everyone is as familiar with delicata. I like to say “Delicata is delectable!” Apart from the texture and flavor (creamy, buttery and rich), the skin is very thin which means it is edible, and you don’t need to peel the squash. That cooked peel adds just the right amount of texture when it’s time to sit down and eat.

In addition to the squashes, I cut up fennel and also add some whole seedless red grapes (get the largest ones you can find because they shrink as they roast). The fennel cooks a bit more slowly than the squashes do, so it provides a bit of a firmer bite. The grapes add a touch of sweetness that offset the heat in the blend of spices. I use brown sugar, cumin, cayenne pepper, ground black pepper and kosher salt. While this “squash mix” does carry a bit of heat, it isn’t too hot. However, if you prefer less heat, add less cayenne – or use a milder red pepper like Aleppo or ancho. Only your own taste will tell you your preference! For garnishing after the dish is cooked, I use fresh mint along with some of the fronds cut off from the top of the fennel.

squash mix

Since I make this dish so frequently through the Fall and Winter, I usually just make a big batch of the squash mix so it’s handy. It minimizes any measuring, and I know it will turn out consistently. To make a bulk jar of squash mix, stir together:

  • 1/4 cup brown sugar
  • 1/4 cup ground cumin
  • 1/4 cup kosher salt
  • 1/4 cup freshly ground black pepper
  • 1/2 tsp cayenne pepper

As you’re mixing, be sure to break up any clumps of brown sugar to blend everything together evenly.

Now all that’s left is to cut up the vegetables. Slicing the squashes into “half-moons” will allow you to easily arrange the pieces in your baking dish. And if you choose to “scatter” instead of “arrange”, they’ll look pretty and hold up nicely as they roast.

I mentioned that the delicata squash has a thin skin – which makes cutting and slicing super-easy! Just cut off the ends so you can stand it up flat and stable:


Now slice straight down, so you end up with two long halves:


Using a spoon, scoop out the seeds:

squash cleaned halves

Then flip the halves over so they’re flat and won’t wobble, and slice them into 1/4"-1/2” half-moons:

delicata squash slices

The butternut squash takes just a little more time because the squash itself is typically larger than delicata and the skin is thicker. However, it is most definitely not the nightmare that many people anticipate it to be! A previous post walks you through the process, so I’ll just summarize it for you here.

As with the delicata, cut off the top and bottom. Then cut it just where the longer “neck” meets the rounder “bottom”:


Next, peel both pieces using a vegetable peeler:

peel butternut

I sometimes find that once I’ve peeled about half of each piece, the squash gets a little slippery to handle because the skin is gone from where I have to hold it. My solution is to just grab a small kitchen towel to hold onto the squash. Ta-da! Problem solved, and I can continue peeling.

Once again, slice both pieces in half, scoop out the seeds (found only in the round bottom piece), and slice them into 1/4"-1/2” half-moons:


For the fennel, I like keeping it super-easy and leaving the core/root intact. Don’t worry: the core will roast along with the rest of the vegetables. While you will likely end up with a little bit of “bite” when the dish is done, it will provide a bit of contrast and will most definitely be soft enough to enjoy. So, just slice the fennel bulb in half, vertically. Then, flat side down, slice each half into six pieces:


For me, the easiest way to do this is to slice the fennel half down the middle. Then, slice each side into three pieces. The end pieces may come apart, but the center pieces will be held together by the root. And you know what? If the slices don’t all hold together – or if you prefer to slice them in a completely different manner! – that’s fine. It’s all about arranging (or scattering!) the vegetable pieces in your baking dish… and you can do that no matter how you slice them!

Now blend your squash mix along with some extra virgin olive oil in the bottom of a large bowl. This is all about taste but generally, I mix about 3 Tablespoons of squash mix with 2 Tablespoons of olive oil. The mixture should be only slightly looser than a paste. This time around, I had to build both a large baking dish, as well as a smaller one for a friend – so I used A LOT of vegetables (1 butternut, 1 delicata, 2 fennel bulbs, 1 pound of grapes). So I blended together 3 times that amount, using 9 Tablespoons (1/2 cup plus 1 Tbsp) of squash mix and 6 Tablespoons (1/4 cup plus 2 Tbsp) of olive oil. Add your vegetables and whole grapes to the bowl, and toss to coat. I like to use my hands to mix everything together, since all my half-moon slices are less likely to break!

squash dish

As you can tell, how much of the squash mix/olive oil you use depends on the volume of your vegetables, but you want a nice coating, as you can see in the photo. You can easily add more if you need to. Keep in mind that the salt in the mix will begin to pull water from the vegetables, so you will likely find some liquid remaining in the bottom of the bowl after you transfer the vegetables to a baking dish.

Now set your oven for 425⁰F. Arrange the vegetables in a baking dish however you like. I like to sprinkle the grapes over the top. Note that there is no need to oil the dish.

grapes and squash

If you decide to “scatter” rather than “arrange”, try to keep  your vegetables no more than two layers deep. You really do want to get some char on the vegetables and if they are buried too deeply, that won’t happen. Using a sheet pan to give you more area to work with will help with that – just don’t forget to line your sheet pan with a piece of parchment to make clean-up easier.

Roast for about 25-35 minutes, until you see some char on the vegetables and hear a bit of sizzling when you check on it. You should also be able to poke the tip of a paring knife easily in and out of the thickest pieces.

finished squash dish

Isn’t the color great? I drizzled a little extra virgin olive oil over the top as soon as it came out of the oven and sprinkled it with torn mint leaves and bits of fennel fronds.  The mint may sound odd, but it really does give a nice little pop of flavor. While this makes a great side-dish, it also works well as a main dish. My husband and I like it over couscous or farro. It’s really flavorful and warming on a cool night. I hope this becomes one of your favorites as well!

Fall is most definitely in the air at The Chopping Block and our classes are reflecting the change of seasons! Check out the Fall versions of our Pasta Workshop and Know Your Gnocchi. In addition, we’ve added Autumn Farmhouse, Fall Dinner Party, and Homemade Butter, Conserves & Jams to our class schedule. And don’t forget your sweet side with our Cupcake Bootcamp: Fall Menu!


Topics: squash, butternut squash, fennel, fall, Cooking Techniques, delicata squash

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