Preheat oven to 400 degrees F. Prepare a sheet pan by covering it with foil.
Lay bacon flat on the prepared sheet pan. Place the pan in the oven and bake for 15 minutes, or until the bacon is brown and crispy.
Remove the bacon from the pan and place it on a paper-towel lined plate to soak up the extra grease. Crumble the bacon into small pieces.
While the bacon cooks, add eggs to a small saucepan. Add water over the eggs until they are submerged in water.
Place eggs on the stove over medium heat and bring to a rolling boil. Once boiling, turn off the heat and let eggs sit in the hot water for 10 minutes.
After 10 minutes, drain the water and rinse the eggs in cold water. Peel the eggs and chop them.
Remove any damaged outer leaves on the head of lettuce. Cut the lettuce in half and remove the core from both halves. Then, cut the halves into half again. You should have 4 equal-sized wedges of lettuce.
Place the lettuce wedges on individual plates or a large serving tray. Top with bacon, eggs, feta, and cranberries. Slice the apples and tomatoes, place them along the sides of the lettuce wedge.
Drizzle with homemade pumpkin salad dressing and garnish with fresh chives.