Cranberry Apple Stuffed Squash

Total Time
1hr 15mins
Prep 5 mins
Cook 1 hr 10 mins

It's fall in Wisconsin! Made this up last night after traveling to our local apple orchard and picking out a beautiful autumn cup winter squash, a 'cousin' of the butternut squash, too good not to share!

Ingredients Nutrition

  • 1 (2 -4 lb) kabocha squash (winter squash) or 1 (2 -4 lb) butternut squash (winter squash) or 1 (2 -4 lb) buttercup squash (winter squash) or 1 (2 -4 lb) autumn cup squash (winter squash)
  • 1 tablespoon butter
  • 1 medium apple, diced
  • 12 cup fresh cranberries, frozen can also be used
  • 2 tablespoons brown sugar
  • 2 tablespoons chopped pecans, toasted
  • 12 teaspoon cinnamon


  1. Preheat oven to 350 and prepare baking dish large enough to hold your squash.
  2. Halve squash and scoop out the pulp.
  3. Place cut side down in baking dish and bake for 35 minutes. I usually add just a bit of water to the dish to keep the squash moist.
  4. About 7-10 minutes before your timer goes off, prepare filling. Heat small saucepan over medium heat, add butter, diced apple, fresh cranberries, brown sugar, pecans and cinnamon. Heat over medium heat until butter is melted, then simmer on low until timer goes off.
  5. Remove squash from oven, flip over and fill with apple/cranberry filling.
  6. Bake an additional 25-35 minutes depending on the type and size of your squash, again adding just a little water to the bottom of your baking dish. Squash is done when fork tender.
Most Helpful

A buttercup squash, which has a sweet creamy orange flesh that tastes similar to a sweet potato, was the perfect vessel for this flavorful stuffing. I recommend using one of the naturally sweeter varieties of apples like a Gala because a sour Granny Smith apple would be too tart paired with the cranberries. I omitted the pecans and added one teaspoon of fresh orange zest which enhanced the flavor of the frozen cranberries. Instead of cooking the filling in a saucepan, I stuffed the raw squash with the uncooked cranberry-apple mixture and baked at 350F degrees for one and a half hours since I was not in a rush. The longer cooking time really allowed the squash to absorbed the delicious flavors of the filling. Since a buttercup squash has a very small inner cavity, there was excess filling. I baked the excess filling with a little water in a small Corningware dish with a lid. After the squash was done baking, its filling settled into the cavity making room to add the rest of the separately baked excess filling. The tartness and sweetness of Cranberry Apple Stuffed Squash was the perfect side dish for my roast lamb. Thank you, Brooke the Cooke in WI, for a combining my favorite flavors of fall into a side dish that is tasty enough to be star of the show!

Garden Gate Kate November 10, 2013

Delicious! I added a little fresh ginger as well to give it a bit of spiciness.

Pizzabeast October 22, 2009

Really enjoyed this I used a butternut & after cutting it gave it rub with a bit of "i can't believe it not butter" and also rubbed a bit of garlic, chili and brown sugar into them -than took advice from JanuaryBride and used fresh squeezed OJ in the bottom of the pan...i added dried cranberry as well as the frozen and did the rest of the stuffing as stated ...served them with herbed & nutty couscous w/ spicy sauce on the side (oh- i also "cut them in half"... length wise to make eating easier)...(you could even eat the skin...:) ) really nice, great flavor and pretty presentation too->Thanks Brooke!

free-free February 12, 2009