Italians use vinegar and sugar to create the flavor they call agrodolce, and the sweet and sour combo is perfect for the subtly sweet roasted winter squash and bitter radicchio in these little three-bite sandwiches. While any winter squash would work, it’s easy to cut the cylindrical delicatas into thin slices, especially for the winter squash curious who might not be ready to butcher one of the pumpkiny varieties like kabocha. And like almost all winter squash, the skin is edible (thick and flinty butternut skin is the exception).
Cut off the stem and a thin slice from the other end, then halve the squash lengthwise. Don’t just scrape the seeds into the compost, they’re delicious roasted. Use the tip of a spoon to tease out the seeds (I do this over a small skillet, and don’t sweat it if some of the membrane gets in the pan, it’ll disappear as they cook). Then use the spoon to remove the rest of the stringy membrane. Add a splash of olive oil, a pinch of salt, and maybe some red pepper or a spice blend, then set the skillet aside while you slice the squash (everything gets roasted at the same time).
While any variety of radicchio works, I prefer the long, romaine-like Treviso over the more bitter Chioggia, which looks more like red cabbage. For any radicchio, it’s a good idea to taste it for bitterness. It can be tamed by soaking the cut leaves in cold water for at least 20 minutes, longer if it’s very bitter.
I’ve yet to find slider-sized buns at the grocery store, but most carry Hawaiian-style dinner rolls, and the slightly sweet, buttery rolls work perfectly. Slice them carefully with a serrated knife, and for an even better sandwich, grill them in olive oil or butter until lightly browned on the cut side. The rolls come 12 to a pack, and you could use them all to make a party platter. If I can exercise restraint, I’ll just make a few sliders at a time and freeze the rest of the rolls. But it’s not that hard to eat a half dozen, either.
Recipe
1 6–8 inch delicata squash, halved and sliced about ½ inch thick
4–5 leaves radicchio, shredded*
2 teaspoons sugar
¼ teaspoon kosher style sea salt
1 tablespoon red wine vinegar
2 tablespoons extra virgin olive oil
2 tablespoons mayonnaise
Hawaiian dinner rolls
*Radicchio can vary in size; you want roughly as much shredded radicchio as winter squash
Put the squash slices in a bowl, add a splash of olive oil and pinch of salt, and toss so they’re lightly coasted. Transfer to a sheet pan and roast at 425F for 25 minutes. Put the skillet with the seeds in the oven at the same time, but give them a stir at least once during cooking. They should be nicely browned and crispy by time the squash is done.
While the squash cools, shred the radicchio by rolling it in a tight cylinder and cutting into ½ inch pieces. I like to cut the longer shreds to about an inch so they mix with the squash better. Make the dressing by dissolving the sugar and salt in the vinegar, then stir in the olive oil and mayo.
Cut the squash slices into cube-like pieces about ½ inch long. Combine them with the radicchio and dressing, then mound a couple of spoonfuls of the mix onto the bottom half of a grilled roll. Add the top, eat, and repeat.

