Preheat oven to 350°F.
Cut the jalapeños into a boat cut. (Click the link above to see how to do a Boat Cut.)
Sprinkle insides of cut jalapeños lightly with salt and pepper, to taste.
Place the jalapeños on a cookie sheet. Place sheet in preheated oven. Cook for about 10 minutes. (Skip this step if you prefer your finished jalapeños to be more raw and crunchy.)
Remove from oven and allow to cool slightly so you can handle them.
Add cream cheese to each jalapeño to cover the bottom, leaving a concave "well" to place other ingredients. (Click the link above to see pictures of this step, if the instructions are unclear to you.)
Fill the well in the cream cheese with a generous helping of Cheddar cheese.
Cut bacon strips in 1/2.
Wrap bacon around each jalapeño. Secure with a toothpick, if you like.
Place jalapeños back on cookie sheet and place back in oven.
Cook, watching closely, until cream cheese is hot and bubbling and bacon is done, about 25 - 30 minutes. Check to make sure jalapeños and bacon are done to your liking. If not, place back in oven for more time.
Remove from oven when done.
Serve hot with blue cheese and/or Buttermilk Ranch Dressings, to dip.