Photo of Roasted pumpkin and chestnut salad with orange-cranberry vinaigrette by WW

Roasted pumpkin and chestnut salad with orange-cranberry vinaigrette

SmartPoints® value per serving
Total Time
1 hr
30 min
30 min
This delectable salad screams fall, combining sweet chestnuts and pumpkin, rich and salty pecorino and the slightly bitter crunch of chicory. Microwaving the pumpkin before cutting makes getting a knife through the dense flesh much easier. Don’t toss the pumpkin seeds. Rinse, dry, season and roast for a tasty snack or salad topping. Great for a Thanksgiving salad, divide the servings in half and serve a whopping 16 people. Ready in under an hour, this main-dish salad can stand alone or top it with some roasted chicken breast for a heartier version.


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

2 Tbsp

Balsamic vinegar

1 Tbsp

Dijon Mustard

1 tsp

Dried cranberries

2 Tbsp, chopped

Table salt

½ tsp

Black pepper

¼ tsp, freshly ground


8 cup(s), 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 pan 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