Words About Wilton: Gail Hoar – What, retire? You must be kidding

Gail Hoar

Gail Hoar COURTESY PHOTO

Dick Rockwood served 40 years in various roles for the Town of Wilton, and still works as a property appraiser.

Dick Rockwood served 40 years in various roles for the Town of Wilton, and still works as a property appraiser. —PHOTO BY GAIL HOAR

Dick Rockwood and his dog, Buddy.

Dick Rockwood and his dog, Buddy. —PHOTO BY GAIL HOAR

Published: 03-07-2025 8:34 AM

Modified: 03-07-2025 2:02 PM


When Dick Rockwood and his wife Jane offered to take my husband to one of his medical visits while I was down with COVID, I realized his is a face that’s been missing from town boards and committees for far too long.

Whichever group he joined was fortunate to have his strong, straightforward, knowledgeable, honest and often opinionated voice offering suggestions or information that may not have been what was expected, but certainly made people look again at their positions on an issue. With this realization, I had the topic for my next column.

If you haven’t lived in Wilton for at least 12 years, you probably have not been fortunate enough to witness Dick in action. He was a fixture on almost every board and committee in town since 1973 when he joined the School Board. He said, “I looked around and saw things I may be able to help with. I think the only board I haven’t served on is the Board of Adjustment.”

His ventures as a Wilton public servant ended when he retired as a town selectman in 2013. During those 40 years, Dick also served on the planning and zoning boards, been a library trustee and offered insight and leadership for years as the budget committee moderator. In March, 2005, Dick represented that role in the Men of Wilton Calendar.

But he may perhaps best be remembered as moderator for both the School Board and Town Meeting. With him at the microphone, you’d be guaranteed the meetings would never be dull and everyone who wanted to speak was given a chance to voice their opinions.

Dick and I sat down in his family room with his dog and cat intermittently demanding attention. When I asked him how he viewed his years of service to Wilton, he replied, “While I was on the School Board, one of the things I really enjoyed was handing out the Blanchard scholarships to students. We always tried to make certain that everyone who applied received something, but I enjoyed the job of town moderator best. I wanted everyone to feel free to say what they wanted without being intimidated. That’s what Town Meetings are all about – citizens freely speaking up about things that concern them.”

In our ensuing conversation, I learned it was Dick’s background that gave him such a solid understanding of so many municipal issues. Even though he is now in his 80s, he is still working in the field that gave him this experience, property appraisals.

“I can’t give it up. I still enjoy going out to do an appraisal,” he said.

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He didn’t just walk into this job. Dick took a circuitous route to get there, starting with retail sales that led to store and then regional management. Somewhere along the way he decided to add real estate agent to his resume and took the exam to be a broker. This led to an encounter that brought him into the world of property appraising.

“It’s not an easy job and takes time, training and attention to details to begin to understand every aspect,” he said. “Now to do the job, you must also be certified and put in at least 1,500 hours of appraisal work with a certified appraiser to be considered qualified.”

Dick had taken enough courses to be certified. He explained to me that being an assessor for tax purposes is a much easier field to enter and less demanding, but to do that job correctly, you should have appraisal experience to understand the details of what you’re looking at. He added, “That’s why property owners often call for advice on their tax bills.”

What was most important to Dick during the time he served Wilton in so many different ways was being able to do something positive that helped others.

“It felt good when I could be part of something that had a positive outcome,” he said. “I enjoyed serving as a selectman, especially when it involved helping someone in need and we could find a solution.”

Often this meant his love of researching issues and gathering accurate information, no matter how he served the town, helped those he served with find solutions to thorny issues – which are exactly the same qualifications needed to be a good appraiser.