Rooting the Motorola Milestone has been a somewhat impossible task given Motorola locking down the bootloader. I say somewhat because some folks at AllDroid have managed to gain root access on the TELUS Milestone, albeit without kernel access.
A good start is better than nothing and there are some directions on how to root the TELUS Motorola Milestone over at AllDroid. I find the poll at the top quite humorous: “Did this thread help any†with the choices all answering questions with questions… one of them “Did you brick your phoneâ€? Feel free to try this out yourself, but if you have to answer the question with the question we noted – don’t blame us!