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Deluxe Caprese Dagwood

Ingredients

Roasted squash and tomato spread

  • 2 cups winter squash, roughly diced
  • 2 cups cherry or Mountain Magic tomatoes
  • olive oil and salt, to taste
  • 2 tsp balsamic vinegar (optional)

Sandwich fixings

  • 1 large loaf of bread, unsliced - we recommend not too crusty, as it will be much harder to eat
  • 1/4-1/2 cup basil pesto, amount depends on your liking and the size of the bread
  • 1-2 cups prepared squash and tomato spread (see cooking notes below)
  • 1 bocconcini, sliced
  • 6-8 slices bacon, cooked
  • several handfuls of lettuce greens
  • mayonnaise, as needed (can sub with butter)

Instructions

Roasted squash and tomato spread

  1. Preheat oven to 400. Toss squash and tomatoes in olive oil and salt on a rimmed baking sheet. Allow to bake until tomatoes and squash are soft and starting to take on colour, about 20-30 minutes.

  2. Transfer to a bowl, and roughly mash with a fork. Add the balsamic and taste to adjust seasoning. Set aside and allow to cool slightly.

Sandwich assembly

  1. No instructions needed for this, really. But start by cutting the loaf in half (as if it were a hamburger bun). An optional step is to then use your hands to remove some of the "innards" from the bread, creating a bit of a hollow. This will make the eating slightly less messy, since the ingredients will then be more "nestled" but it's not required.

  2. Spread mayo (or butter) on both halves of the bread. Be generous as this is a protective layer that will help prevent your bread from getting too soggy.

  3. Spread basil pesto on top of mayo (we just did on the bottom half), then spread the roasted squash and tomato on top. Add bocconcini, bacon, and a generous amount of greens. Slap on the top, and you're set! We had a large loaf and cut it into 5 good-sized pieces. Serve with salad if desired.