Preheat your oven to 400°F (200°C).

Halve the butternut squash lengthwise and scoop out the seeds, placing cut-side up on a baking sheet. Drizzle with olive oil and season with salt and pepper.

Slice off the top of a whole head of garlic, drizzle olive oil over the exposed cloves, wrap in foil, and place alongside the squash on the baking sheet.

Roast the squash and garlic for 45–50 minutes until tender. Check doneness with a fork.

Allow to cool for about 10 minutes, scoop the squash flesh into a mixing bowl, and squeeze out the roasted garlic cloves.

Mash the squash and garlic together, gradually adding in the butter and heavy cream until creamy.

Season with salt and black pepper to taste.

Transfer to a serving dish, drizzle with olive oil or melted butter, and garnish with fresh herbs if desired.