Preheat oven to 400 degrees.
Cut butternut squash in half and scoop out seeds from center.
Place in roasting pan with flesh side up.
Place 1 tablespoon of butter in each center of each half.
Drizzle maple syrup on each half and sprinkle with brown sugar and salt and pepper.
Place in oven and cook until tender for approximately 50 to 60 minutes.
Let cool and scoop cooked squash from flesh.
Mash the squash so that it is smooth and creamy. Feel free to add a little more butter or salt and pepper to taste.
Place to the side.
Over medium heat in a pan add olive oil and add onion and cook until onions soften.
Add chicken and garlic and season with salt and pepper.
Cook until chicken is no longer pink.
Add sweet potato, russet potato, and granny smith apple.
Stir in wine and cook for a minute or two.
Add chicken broth and cook until potatoes begin to soften.
Add cream of mushroom soup and poultry seasoning.
Stir to incorporate. You may need to add a little more chicken broth if mixture seems to thick.
Add bag of frozen vegetables and continue to cook until vegetables thaw and warm.
Spoon chicken mixture into ramekin and top with the mashed butternut squash.
Place in oven and cook until squash browns, about 10 minutes or so.