I’ve never heard the term. Reading the Wikipedia article, it looks like the term was used more down south.
In New England, after receiving a patent or charter to settle from the crown, towns were authorized for settlement by the Provincial (Colonial) Governments. In Mass. they usually tried to purchase the land from the local tribes before settling, but not always. I think the earlier settlements were more likely to involve negotiation with the tribal sachem and the recording of a deed than the later settlements, after the various French & Indian wars. There was probably more of a “right of conquest” approach by then. Anyhow, the Proprietors-Selectmen of the new settlements would grant lands to the new settlers as they moved into town. These would probably qualify as headrights, though as I noted I’ve never seen the term used. The settlers may have had to pay the towns for their lands, with the money being used to build roads, bridges, and churches. Later, the Revolutionary War militiamen were paid for their service with land grants by the Provinces. There were no federal lands within the original colonies. I think the federal government may have paid the regular army and navy service men with land grants in the unorganized territories won from Britain (but disputed for ownership by the newly formed states for some years).