The Millerton News’ candidate profiles for Town Board and town supervisor follow below. The candidates each wrote 100 words about themselves to share with voters why they should be elected.
Pine Plains Town Board Member
Diana Woolis (D)
Town Board candidate
I am a proven leader, who finds creative solutions to challenging problems through listening, engaging others in the process and respecting a diversity of opinions.
Successful leadership in government, nonprofits and as founding partner of a digital company, I have served Pine Plains, State and City government, and now work globally to assure quality education for all.
My goals include: sustainable economic development and building on what’s here (farm, table and tour to bring visitors and new businesses); affordable housing (to keep families and attract newcomers); and strengthening town infrastructure (broadband, waste management, sidewalks and a vibrant town center).
Matthew Zick (NOP, endorsed by
Republican and Democratic parties)
Incumbent
Town Board member
Running for second term.
I’m proud of my first term on the Town Board and am running for a second. My wife and I and our two young daughters live in the hamlet.
There are current projects I hope to see to completion.
I successfully helped settle a long unresolved tax issue with the Fire Company.
I’m very active with the Recreation Committee and passionate about strengthening our programs and facilities.
I helped purchase the outdoor winter ice rink, install it and maintain it for two successful seasons.
I’m always open to talking with voters and would appreciate your support this Election Day.
Pine Plains Town Supervisor
Brian Walsh (R)
Pine Plains Town
Supervisor Candidate
Born and raised in the town of Pine Plains, I have felt it to be my duty to work tirelessly to support my community.
For five years I held the title of fire commissioner and the past six years, of fire chief.
As supervisor, I plan to start by tightening the budget to relieve taxpayers, upgrade recreational fields and improve sidewalks.
I will focus on one project before moving forward to the next, keeping our community informed while being open to any opinions or concerns.
My leadership and dedication are proven.
Darrah Cloud (D)
Incumbent Town Supervisor
Running for third term.
I do not have a political agenda — I have a Pine Plains agenda: To bring Town Hall back into town; to find funding and permission to build a small central septic system in Pine Plains for the business district; to continue the Town Board’s collaboration with the developer of the Hudson Valley Project; to protect and develop economic strategies that are sustainable for both generations and the environment; and to fulfill the goals of the Comprehensive Plan.
I have the experience and the time to continue the work I have already done toward accomplishing these things.
Robert Ambrose (R)
Pine Plains Town Board candidate
My name is Robert Ambrose, a Pine Plains native for 45 years running for Town Board. I want to give back to my community and make a difference.
I am a life member of the Pine Plains Hose Company with 25-plus years of service. I was a fire commissioner for the fire district.
I want Pine Plains to become more affordable for people to come to live and the ones that do, to stay here.
I want to help the town evolve and be the best it can be, so Pine Plains is a place people want to come to.










Cella’s paintings are tucked in almost every available space thoughout Little Store Antiques. L. Tomaino


Jerron Paxton & Nora Brown at Oldtone Music Festival in 2025.Reed Shuzts


