Preheat the oven to 350 degrees Fahrenheit.
Slice the pear in half and remove the seeds and stem. Use a spoon to create a small cavity where the seeds were.
Place the pear halves cut side up in a roasting pan. Drizzle the cut sides of the pear with maple syrup and then sprinkle on the cinnamon.
Remove the shell from the chestnuts and discard. Place a chestnut in each pear half.
Roast for 30-35 minutes and serve warm.