Yes, you can take him to small claims court. I haven't done it, so I can't tell you the details of the process, but it's supposed to be fairly simple and it can be done without an attorney.
As for the "lien," just to be clear, what a statutory road association allows is not a true lien, but a notice of claim. The difference, as I understand it, is that a true lien has a required timetable ending in taking the land. It can be a rather complicated undertaking. A notice of claim simply goes on record in the registry of deeds, and remains there until it is settled. That means that if the person goes to sell his land, he will have to settle the claim first. It also will pop up on his credit rating, which means if he wants to take out a loan, he'll have problems. Many people find that to be a powerful incentive for settling.