Legal Question in Constitutional Law in Massachusetts

On private property probably. On roads no. There is no such thing as a right to travel. Driving is a privilege

No. You do have a right to travel within the U.S., but that does not mean you have the right to operate a motor vehicle. You can travel as a passenger in someone else's vehicle, by bicycle, by horse, or on foot. But motor vehicles are much more likely to harm other people if driven by someone who does not know what he's doing. The government has a legitimate -- indeed, a compelling -- interest in making sure people who drive know how to do so safely. You have no more right to drive a car without a license than to fly a plane without one.

You are subject to the laws of your state whether you have a driver's license or not. That is just as true of registration and insurance laws as any other. It might not be possible for an unlicensed driver to comply with those laws, but that does not mean lacking a license frees you from the requirements. It just means that you will simultaneously violate multiple laws if you drive without a license.