Can a private landowner plow a seasonal road to access his property?
If the landowner does plow the road he should have a contract with the town to provide snow plowing services. The contract should specify the requirements, duties, liability, payments, etc. If the town employees are unionized it could trigger a need to negotiate with the union the sub-contracting of their work to a third party.
It may also impact the town’s authority to designate the road as seasonal since the road is not closed, just that it will not be maintained in the winter. If the landowner does not need access on a regular basis, he may be able to make arraignments with the town in advance to make sure the road is open. Alternatively, maybe this is a road that could be abandoned and turned back to the abutting property owners under Town Law, Section 205
Anytime work includes outside service providers, the Town Attorney should be consulted to protect the municipality from any kind of liability.