Legal Question in Administrative Law in Massachusetts

This is an interesting, thoughtful question. Frankly, I don't know the answer off hand, but agree your analysis does make some sense and probably deserves to be further explored. Feel free to contact me directly to discuss this further, without obligation to you. Good luck.

I am not familiar with this particular statute, and so I can only give you my best guess. However, in light of the non-mandatory language contained in the statue, I do not see why the Town would be compelled to continue to plow these private roads.

Private roads may not receive an entitlement to plowing services from a municipality unless and until they are "accepted" by the Town. Littleton has a Town Meeting style of government and a Warrant to accept the road would need to voted by the majority of persons in attendance.

Before a road can legally be accepted, it must be built to standard (comply with the then existing code) with adequate drainage, width, grade and with proper materials. Only after a road has been accepted can a town receive state highway funds to offset the cost of plowing and maintaining the road. Towns may not use public moneys to plow and maintain private roads, with limited exception.

Getting a road accepted requires either that the municipality fund the project from general revenue (rare) or by a special assessment (normal) to the abutting property owners and any who benefit from the improvement. When done by the municipality, it is subject to government contracting requirements and the prevailing wage act. As a homeowner on a private road, you may be eligible to petition the court to appoint either yourself or another homeowner to act as a lead or point person to oversee the construction (privately contracted) and assess the abutting homeowners their proportionate share of the costs. Once the road is built to standard, you can petition the Town to have it accepted and deeded over to the Town of Littleton, at which time, the town would assume liability for maintaining and plowing the road.