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Election 2026: Tom O’Brien Discusses Roxbury Town Supervisor Race

Democratic candidate Tom O’Brien joins Radio Catskill’s Kimberly Izar to discuss his campaign for Roxbury Town Supervisor, his experience as a school superintendent, priorities for Roxbury and Grand Gorge, and his challenge against incumbent Town Supervisor Allen Hinkley in November.
Election 2026: Tom O’Brien Discusses Roxbury Town Supervisor Race
Tom O’Brien (Photo: Tom O’Brien for Roxbury Supervisor campaign)

Democratic candidate Tom O’Brien joined Radio Catskill’s Kimberly Izar to discuss his campaign for Town of Roxbury Supervisor, his experience in education and the issues facing residents of Roxbury and Grand Gorge ahead of the November election.

O’Brien is challenging incumbent Town Supervisor Allen Hinkley. A longtime Roxbury resident and former Roxbury Central School superintendent, O’Brien said his experience managing school districts has prepared him for the responsibilities of town government.

During the interview, O’Brien discussed his career in education, including serving six years as principal and more than 12 years as superintendent of Roxbury Central School. He retired in 2020 and has since worked in interim administrative positions, including at Stamford Central School.

O’Brien said many of the responsibilities of a school superintendent are similar to those of a town supervisor, including managing budgets, personnel, contracts and negotiations.

Government transparency was a major focus of the conversation. O’Brien said residents have expressed concerns about communication from town officials and the process through which decisions are made.

He called for a more open approach to town government, including providing residents with clearer information about board discussions, decisions and major developments affecting the community.

On town finances, O’Brien discussed the importance of long-term budget planning. He said budgets should not be considered one year at a time, but should account for historical spending, revenue trends and projected expenses.

The conversation also addressed development and how Roxbury can accommodate new residents and businesses while maintaining its rural character. O’Brien said the town should use its comprehensive plan to help guide future growth.

He also discussed the relationship between longtime residents and newcomers, emphasizing the importance of bringing different groups together as the community changes.

O’Brien pointed to the Roxbury Partners independent ballot line as part of his effort to encourage cooperation and community involvement.

Environmental protections and development within the New York City watershed were also discussed. O’Brien said the town must balance watershed regulations with opportunities for housing, business development and improvements to existing properties.

He emphasized the importance of maintaining working relationships with the New York City Department of Environmental Protection, New York State Department of Environmental Conservation and other agencies involved in local development.

O’Brien also discussed the role of organizations such as the MARK Project in securing funding for improvements in Roxbury and Grand Gorge.

Infrastructure and road safety were additional concerns. O’Brien called for improvements to roads, intersections and pedestrian crossings, including the intersection in Grand Gorge and crosswalks near Roxbury Central School.

He said the town should work more closely with the New York State Department of Transportation to address road conditions and pedestrian safety in both communities.

When asked why voters should choose him over Hinkley, O’Brien pointed to his experience in school administration and discussed his approach to town leadership, emphasizing transparency, communication and collaboration with residents.

He also discussed his connections to the community and his belief that Roxbury should remain welcoming to new residents and businesses while preserving the qualities that make the town distinctive.

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