Can Town Highway Superintendent plow a public official's driveway?

Generally No, with a few exceptions when the driveway is needed for Town business or during an emergency.

The following is from the Association of Towns of the State of New York explaining when Towns can plow snow from private property.

General Rule

The State Comptroller’s office has opined that since town property is acquired only for proper town purposes, it may not be used for purely private purposes (Op. St Comp No. 88-41, p 81; 1983 Op. St Comp, No. 83-103, p 127; 23 Op. St Comp, 1967, p 762; 16 Op. St Comp, 1960, p 56).  Therefore, the town highway department may not use town resources to remove snow and ice from private roads, parking lots or driveways unless an exception applies (Op. St Comp. No. 90-59).

Exceptions

The State Comptroller’s Office has recognized a few exceptions to this general rule:

Town Office Exception

A town may remove snow and ice from private property in order to provide access to a town official's home which is also used as his or her official office (Op. St Comp No. 77-672, (unreported)).

Emergency Access Exception

The highway department may remove snow and ice from a private road in order to provide immediate access to emergency vehicles attempting to access a private residence in order to provide immediate aid. It is important to note that the town may not regularly plow and sand a private road belonging to a disabled individual - the exception applies only to emergencies (Op. St Comp. No. 90-59).

Contractual Obligations Exception

The State Comptroller’s Office has opined that a town may agree to routinely plow snow from the private property of a volunteer ambulance corps as consideration for services provided by the corps under a contract with the town in order to facilitate the efficient provision of ambulance service within the town (Op. St. Comp. No. 82-123).

A town may enter into an agreement with the owner of a parking lot pursuant to which the town would lease a portion of the lot for town parking purposes and, in consideration therefore, would agree to plow snow on the portion of the property not used for town parking if the snow plowing is primarily in furtherance of a proper town purpose and the value of the services to the owner, plus any other consideration provided by the town, is commensurate with the value of the benefit received by the town under the lease (Op. St Comp. No. 92-42).

Resources

Legal Opinions of the NYS Comptroller from 1988-present
http://www.osc.state.ny.us/legal/index.htm

For Legal Opinions prior to 1988, the Comptroller has an online form that can be used for requests - http://www.osc.state.ny.us/legal/form/requestform.htm - or you can call 518-474-5586.

Association of Towns of the State of New York

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