Get out 2 or 3 cookie sheets and line them with parchment paper or silicon mats.
Very carefully twist the tops off of all the Oreo's and set all of the Oreos on the prepared cookie sheets. Don't over crowd them, you do not want them touching each other when you put them back on the silicon mat.
Melt 1/2 cup chocolate over a double boiler. Once chocolate is melted dip the end of a lollipop stick in candy and gently push it into the cream side of the Oreo half way in and all the way down.Then top the blank side of the Oreo with a small amount of chocolate and sandwich it with the other side of the cookie. Do this for all Oreos and then let them sit for 10 minutes.
Once the 10 minutes is up and your Oreo cookies have hardened, melt the remainder of your chocolate using a double boiler.
Then dip the Oreo into the melted candy, turning to cover them completely. Tap the stick on the edge of the container to get of the extra chocolate carefully.
Set the dipped Oreo Pop on it's back on one of the prepared cookie sheets and sprinkle with the crushed candy cane.
Do this until all Oreo Pops are done.
Let sit on silicon mat for 30 minutes, until all chocolate has cooled and hardened. Then you can use plastic treat bags to make them travel friendly or store them in an air tight container.
If you are not making the Chocolate covered Peppermint Oreos into pops, skip the first steps for inserting the lollipop stick and use a fork to dip the Oreos into the melted chocolate.