Prepare the Stuffing

• Hollow out the cooked acorn squash wedges, keeping enough squash integrity to hold up to stuffing & baking. Scoop the squash into a medium bowl.
  
• Mash about a 1/3 cup of cooked potato (skin removed) and add it to the bowl of squash.  (Optional)
  
• Add a sprinkle of salt & pepper to the squash & potato mixture and mash it up until smooth. Warm it in the microwave for about a minute so it's warmed through and stir in 1 1/2 tablespoons of butter.
• Add 1/4 cup chopped pecans to the squash mixture.
• Coarsely chop the dried cherries and add them all to the squash mixture. Taste and add a small pinch of salt if necessary.
  

Prepare the Topping

• In a small bowl, combine the brown sugar, cinnamon, crushed crackers, remaining pecans, and 1 tablespoon butter. Microwave for about thirty seconds or until the butter melts. Taste, and if needed add a sprinkle of salt.

Stuff the Squash

• Divide the squash stuffing mixture between the acorn squash wedges.
• Using half of the remaining butter, dot the tops of the stuffed squash.
  

Add the Topping

• Top the stuffed squash wedges with the pecan topping. 
• Drizzle the olive oil over the topping.
  
• Using the remaining butter, dot the top of the squash filling.

Use an 8x8" pan, or cast iron pan large enough to hold the squash wedges side by side. Add a couple tablespoons of water to keep the pan from burning.

Bake, broil or grill over indirect heat for about 10-15 minutes, or until the top is browned and crunchy. Be very careful when serving. It will stay hot a long time!