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Preheat oven to 375°F (190°C).
Cut squash in half and scoop seeds and flesh from skin, leaving hollow shell. Reserve flesh in bowl for later use.
Lightly brush outer surface of squash shells with olive oil and season with sea salt and pepper. Place on baking sheet.
In skillet over medium heat, cook sausage until it's slightly browned, breaking it into small pieces as it cooks. Add chopped onion and minced garlic. Sauté 2-3 minutes, until onions are translucent and fragrant.
Stir in reserved summer squash flesh and cook an additional 3-4 minutes until it softens.
Remove skillet from heat and stir in breadcrumbs, grated Parmesan cheese, cherry tomato, basil leaves, sea salt, and pepper. Stir everything until well combined.
Carefully fill each hollowed-out shell with sausage stuffing mixture. Press down gently to pack filling. Place stuffed shells in preheated oven 25-30 minutes, or until squash is tender and tops are golden brown.
Remove stuffed summer squash from oven and let cool a few minutes before serving.