Week 15: Deluxe Caprese Dagwood

This sandwich is large and very much in charge. It’s a delightful blend of the flavours and textures of a classic caprese and BLT – with some squash thrown in for good measure! Not only is it a playful merging of sandwiches – it’s also a bridge between seasons as we continue to celebrate the tomato while we bring in the winter squash! The result is delicious, filling, and fun. Feel free to put your own spin on it, or lean towards one kind of sandwich or the other (leave out the bacon, forget the cheese, etc). It’s a pretty fun way to share a meal with friends or family.

We made our own pesto (basil, walnuts, parmesan, olive oil, lemon juice, salt), but here is a recipe from the blog you can use. There’s also a handy pesto template recipe, that helps you to mix and match while creating your own pesto.

Deluxe Caprese Dagwood


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)


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.