Peel, seed and cube 1 medium butternut squash (about 2½–3 lbs). Quarter 1 large onion. Peel 3 garlic cloves (leave whole). Toss squash, onion, and garlic with 2 Tbsp olive oil, a generous pinch of salt and some black pepper. Spread in a single layer on a rimmed baking sheet (don’t overcrowd — use two sheets if needed).
Roast 25–35 minutes, turning once, until edges are caramelized and squash is very tender.
Peel, core and roughly chop 2 ripe pears (Bosc or Bartlett). Keep them reasonably firm
Half way thru the roasting add the chopped pears
Peel & finely grate 1 Tbsp fresh ginger and zest 1 orange (reserve a little zest for garnish if you like).
When the squash/onion/garlic are done, transfer them to a large pot. Squeeze the roasted garlic from its skins into the pot.
Add 4 cups vegetable stock, 1 Tbsp grated ginger, zest of 1 orange (plus a squeeze of juice if you want more brightness), ½ tsp ground cinnamon, ¼ tsp nutmeg, and a pinch of red chili flakes (start small — you can always add more at the end).
Bring to a gentle simmer and cook 10–15 minutes to let the pears soften and the flavors marry.
Tip: If you want a deeper savory edge, add a bay leaf or a sprig of thyme while simmering and fish it out before blending.
Remove the pot from heat. Use an immersion blender and blend until silky and smooth. OR transfer to a countertop blender in batches (fill blender no more than 2/3, remove center cap and hold with a towel to vent — very hot liquids expand). Blend, then return to pot.
Check consistency: if it’s too thick, add up to ½–1 cup more stock or water and rewarm.
Stir in ½ cup heavy cream or full-fat coconut milk for richness. Reheat gently (don’t boil if you used cream; just warm).
Taste and adjust: more salt, black pepper, extra orange juice for brightness, or more chili flakes for heat. If you used coconut milk and want less coconut flavor, add an extra squeeze of orange.
If you want a touch more zing, grate a tiny bit of fresh ginger over the top just before serving.
Notes
Roast for flavor. Deeper the caramelization on your squash and onion, the richer your soup. Balance the sweetness - with the ginger, orange zest, and chili flakes. If the soup tastes too sweet at the end, stir in a squeeze of orange juice or a splash of apple cider vinegar.