Photo of Roasted Pumpkin and Chestnut Salad with Orange-Cranberry Vinaigrette by WW

Roasted Pumpkin and Chestnut Salad with Orange-Cranberry Vinaigrette

Points® value
Total Time
55 min
30 min
25 min
Don’t toss the pumpkin seeds. Rinse, dry, season and roast for a tasty snack or salad topping.


Uncooked pumpkin

2 pound(s), fresh, whole sugar pumpkin (or kabocha squash)

Cooking spray

10 spray(s)

Uncooked European chestnuts

1 cup(s), halved, peeled frozen (or use water-packed jarred chestnuts)


1 small

Olive oil

1 tbsp(s)

Balsamic vinegar

1 tbsp(s)

Dijon mustard

1 tsp(s)

Dried cranberries

2 tbsp(s), chopped

Table salt

½ tsp(s)

Black pepper

¼ tsp(s), freshly ground


8 cup(s), chopped, chopped, torn, chicory variety

Grated Pecorino Romano cheese

1 cup(s)


  1. Preheat oven to 450°F. Line two baking sheets with aluminum foil (or just coat with cooking spray).
  2. Microwave whole pumpkin (or squash) for 1 minute to make it easier to cut. Using a heavy-duty knife, cut stem end from pumpkin. Put pumpkin cut side down and halve lengthwise; remove and discard seeds (or save for other use). Cut unpeeled pumpkin into 1/2-inch wedges.
  3. Spread pumpkin wedges on prepared pans, cut side down, in a single layer; lightly coat both sides with cooking spray. Roast until lightly golden, about 15 minutes.
  4. Remove pans from oven; flip pumpkin wedges with a spatula. Add chestnuts to pans; roast until pumpkin is golden and just tender when pierced with a knife, about 15 minutes more.
  5. Meanwhile, zest orange into a large bowl. Halve zested orange; squeeze to yield 2 Tbsp juice and add to bowl. Add oil, vinegar, mustard, cranberries, salt, and pepper to bowl; stir to combine.
  6. Add chicory, roasted pumpkin, chestnuts, and cheese to bowl: toss to combine. Divide among 6 plates and serve.
  7. Serving size: 1 1/2 cups salad with 4 pumpkin wedges