I really love this recipe for a couple of reasons. First, you can process 10 lbs of market-fresh tomatoes without having to cut, peel, or seed a single tomato. No standing over a hot stove, either! Plus, it freezes really well, the ingredients are simple to find and pretty inexpensive, and, of course, it has great flavor from the deliciously buttery browned squash and the fresh, ripe tomatoes. It also passes the toddler test: familiar, slightly sweet and yummy, very healthy, and able to be eaten with hands or silverware (eater’s choice!). Last, the butternut squash really extends the amount of sauce you get without being nearly as costly as tomatoes. For me, it’s really a miracle harvest recipe, which is why I’ve been making it every summer for the past few years just as soon as big boxes of paste tomatoes and butternut squash start showing up at the market. It’s very forgiving, so adapt it to suit your tastes and what’s available. This is best done early on a lazy summer afternoon, because although you don’t have to do much work, it does take a while. It’s especially nice to do during that seemingly inevitable fake-fall cool front that sometimes comes in during late August or early September, because roasting can make the kitchen heat up.
First, you’ll be using whole, unpeeled tomatoes for this recipe. No blanching, peeling, seeding, or cutting involved. Pre-heat your oven to 425°. Wash and dry the tomatoes, then evenly divide the tomatoes between two large rimmed baking sheets. Drizzle with just enough olive oil to coat when gently hand tossed. Don’t overcrowd the tomatoes too much or they: a. won’t roast well, and b. the juices may overflow off the baking sheets, creating a huge mess for you. Hence, two baking sheets instead of one.
Roast tomatoes until they are browned and starting to split and collapse, about 40-50 minutes. (Less if they’re all on one oven rack).
Meanwhile, chop the top from your butternut squash, halve it, then scoop out the seeds. Chop your onions into large chunks (quarters or eighths, depending on the size of your onions). Prepare your garlic by cutting off the top and bottom of the entire head (keep it together if possible), drizzling it with just enough olive oil to lightly coat (too much and it’ll fry instead of roasting), and wrapping the heads in foil.
Once the tomatoes are finished, take them out of the oven very carefully (there’s likely to be some very hot and very swishy liquid in the sheets). Put the butternut squash (cut-side down), the onions, and the garlic bundle on a baking sheet and roast for 30 minutes. The squash may need a little more time, but be sure to pull the garlic out as soon as it’s soft and squishy (20-30 minutes), or it will burn. You know the squash is done when the top is slightly browned and bubbling. You can put the tomatoes, the squash, and the rest in together if you have an awesome kitchen like my mother-in-law (she has 2 stacked ovens!), but if you have a tiny apartment-sized oven like me, then you have to roast in batches. (If you have a normal oven, I don’t know! Experiment! Maybe you can get it all in. Be aware that adding more pans increases cooking time).
While the squash is cooking, process the tomatoes in the food mill using the medium-sized disk. Revel in the glory of not having to skin or peel your tomatoes. If you finish the tomatoes before the squash, then put the pot in the fridge to keep it cool until the squash is ready.
Let the squash, onions, and garlic cool to the touch. Once they’ve cooled, you can very easily scoop the squash out of the skin using a large spoon (See? You’re rewarded for your laziness here), then blend the onions, squash, garlic, herbs, balsamic vinegar, and salt into the pot with the tomatoes with a hand blender. Celebrate how much that bulked up the sauce for so little cost. You have so much more to put in the freezer for a future lazy evening! Almost double!
Toss with your favorite pasta and enjoy. I often sprinkle (or pour) some parmesan on top. I also like to pair it with a spinach salad tossed with a bit of balsamic vinaigrette and topped with goat cheese. Put the rest into freezer-safe jars (I use glass ball jars with freezer-safe lids), label, and stick in the freezer.