Meet the candidates: Four vie for two one-year seats on Chester Select Board

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The Chester Telegraph sent a series of questions to the four candidates who are vying for two one-year terms on the Chester Select Board. Those two seats are currently held by Leigh Dakin and Jeff Holden, who are seeking re-election. These questions are currently on issues top of mind for many Chester voters. Lee Gustafson is running unopposed for the 3-year seat he currently holds. He was not sent these questions. The candidates were asked to keep their answers to 200 words and lightly edited for style, spelling and grammar.

Voting will take place on 9 a.m. to 7 p.m. Tuesday, March 1 by Australian ballot at Town Hall, 556 Elm St. in Chester. Or you can pick up an early voting ballot at Town Hall.

1. What would you like our readers to know about you? (You can write about your family, your career, how long you have lived in Vermont or Chester, an accomplishment.)

Ben Whalen. All photos by Shawn Cunningham.

BEN WHALEN: Hello Chester! Ben Whalen here. I am a Chester native with a family history that spans from coast to coast. As much as I love to travel, there is something about crossing back into Vermont and making it home to our small town that will continue to keep me here. My spouse and I have two children each, giving us a grand total of four boys!

They certainly keep us busy and currently attend Chester Andover Elementary School in grades one, three, four and five. I previously served four, one-year terms on the Chester Select Board before deciding to take some time off. I work for the Vermont Fire Academy, I am assistant chief of the Chester Fire Department, member of the Vermont Urban Search and Rescue team, and serve as president of the Yosemite Engine Company. I have missed serving on the board and feel I will be a strong voice for the public we serve. We need to maintain a community that supports businesses of all types and one that also supports all the people who live here.

John Keller


JOHN KELLER: I recently moved here about a year ago from Indiana. I came here for a long-term work opportunity in the telecommunications industry but I’ve grown quite fond of Vermont and Chester in particular. I’m in the planning stages of starting a culinary business locally here with my significant other.




Jeff Holden

JEFF HOLDEN: I am Jeff Holden and I am running for reelection to the Chester Select Board for a 1 year term. I am a lifelong resident of Chester and grew up on the farm right here in the Depot. I spent over nine years in the Vermont Army National Guard and am currently an active member in the American Legion at Post #67 here in Chester as an officer and a manager.

I have served the community in many ways including 22 years in the fire service, 27 years in the Emergency Medical Service, 19 years as a patrol officer for the Chester Police Department as well as fire warden and constable.

I have worked for town government for almost 32 years starting out with the highway department then worked into the water and wastewater departments, of which I am currently the superintendent and running both departments. So I have a great deal of knowledge about this community and have nothing but the best interests and hopes for its future.

Leigh Dakin

LEIGH DAKIN: As a resident of Chester for more than 40 years, I, supported by my husband, Bill Dakin, have enjoyed my involvement and participation in many community and school activities, guiding our kids through the joys and challenges of growing up in Chester, operating a small business designing and crafting custom tiles, working as a visiting nurse in the region, as a school nurse in Bellows Falls, Saxtons River, Chester and Cavendish, and serving my town as a member of the Chester Select Board for 11 years and as a member of the Vermont legislature for six years.

Giving back to my rural community of Chester has been a joyful and successful commitment reflected by the education and training achievements of our public school students, the growth of our town library, the support of the expansion of our town recreation activities enjoyed by our kids and others of all ages, whether at the town pool, on the school playgrounds, the support of the construction of our new emergency services home for our police, fire and emergency responders, by the improvement of our town water and sewer systems and by the improvement of the walkability within our town for our residents and visitors.

I am proud of my involvement on the Select Board and in the legislature that, along with the work of many others, has developed a community that is enjoyably livable for our residents, our business owners and our visitors.

Photo by Cari Dobbins for Pixabay.

2. Past Select Board members have had a variety of
attitudes toward economic development.
What do you believe is the town’s role in promoting
economic growth/development in Chester?



JOHN KELLER: I believe in the free marketplace, allowing businesses to thrive with as little regulatory oversight as possible. I’ve been following the cannabis sales regulation debate and see merit on both sides of the equation. More research definitely needs to be done before a decision can be made. I find the program on buying meals from local restaurants and giving them to the public intriguing. I’m sure that at the time of its inception it seemed necessary but most recently it seems to have gone awry. The vehicles I see lined up for “free” meals (ultimately from the taxpayer) seem to be the type that an individual of means would be driving.

JEFF HOLDEN: I am a strong believer in small business for the community. However we need to make sure that we have adequate utilities that can service them, i.e. water and wastewater, and not over -extend ourselves to the point that we would not be able to provide these basic services to the rest of the community. We also need to be sure that any new businesses do not have an adverse affect and not fit into our Town Plan as it is laid out.


LEIGH DAKIN: Our town economy is spurred by the creativity and hard work of our local business people and I subscribe to the importance of local support of our business owners. And many Chester businesses play a major role in the success of the economy of our town and our region, as we count NewsBank and Drew’s (now Schlotterbeck & Foss) as significant employers in and supporters of our town.

The stability of our local and regional economies enhances our town as a desirable residential community for our residents and visitors and for many families whose employment is elsewhere.  Our hard work to maintain and improve our local economy is aided by our collaboration with Springfield Regional Development Corp. and Mount Ascutney Regional Commission as they join us to support our existing businesses and attract new businesses to our community and our region.

BEN WHALEN: Economic development is important to sustaining any community and Chester is no different. We need zoning that aligns with the Town Plan and New England feel, but also something that brings all types of business. Major (locally speaking) blue-collar business have started leaving town. These are hard-working folks that we depend on as a community, and we need them to feel like they can stay. Just as important is keeping Chester as a place that families want to stay and raise their families, grow old, move to, etc.


Photo by Hans for Pixabay.

3. Short-term rental regulations are being discussed in a number of neighboring towns that are worried about the lack of housing, but also noise, crowded roads and other problems that they believe such rentals are bringing. What should Chester be doing, if anything, in terms of regulating the housing stock as short term rentals?


JEFF HOLDEN: There is still more to be done on our zoning regulations and we need to be careful not to make them too restrictive so that they will not hamper the measured growth of the community but will allow us to maintain our small town charms. Not an easy task.



LEIGH DAKIN: See answer to Question 4.





BEN WHALEN: I think we need to see how the State House aligns on this during the legislative session and move forward from there. This will give definition to how these housing units are regulated and place requirements for safety and potentially tax. I think it’s good that people that would typically stay at Jackson Gore or Okemo are renting homes within our community, using our stores, restaurants, etc. This certainly does cause a toll on our infrastructure and that needs to be addressed and this is where we need to see how things turn out or look for something locally. When you look at the housing market there isn’t much there; If those houses that would typically be for sale are locked up in short term rentals that could be a concern.

JOHN KELLER: As long as individual homeowners are renting spaces and not Wall Street real estate buying groups then I don’t see a problem with short-term rentals. We have several inns that do the same. Why shouldn’t an individual have the opportunity to rent their personal property space? I believe, ultimately, it will bring more revenue to the town.



Photo by Ksenia Chernaya for Pexels.

4. Affordable housing has long been a problem in Chester, and the recent hot pandemic real estate market has made it more difficult to find affordable housing stock – both rentals and purchases. What can/should the town/Select Board do to help with this problem?



LEIGH DAKIN: The reduced availability of housing for purchase and rental in our town and in the region in this current robust real estate market raises concerns about increasing our housing availability. Current high construction costs for new and renovated housing units challenge the ability of individual landowners to commit to the building of homes or apartments. The limitation of state of Vermont new- housing funding to only non-profit organizations and the lack of good sites in the Chester area for new residential housing have slowed the increase of new housing in our town and region.

With any housing development proposal, the availability of starter homes and housing units for new families and our local workforce is an important requirement. If short-term rentals are having an impact on the availability of housing for our younger families and re-locating workers, then this is a matter for discussion at the Select Board and Planning Commission meetings.  As our town zoning regulations are currently being revised and updated by our Planning Commission, this is a good time to raise these issues.

BEN WHALEN: This is a problem (for those that are buying) throughout the state but especially in Windsor and Windham counties. I recently read that by the time the housing market drops in the next six years, inflation will have housing prices remain essentially neutral. I think all options need to be investigated, but first off would be trying to maintain the tax rate and doing what we can in local government.


JOHN KELLER: I believe in the open marketplace. I do believe that this current bubble will pop shortly. I definitely don’t agree with the local municipality buying up property to turn into housing, I’ve never seen that go well and I doubt that the local homeowners would like anything like that here.



JEFF HOLDEN: See answer to Question 3.





Photo by Dad Grass for Pixabay.

5. Chester voters will be deciding whether to allow the retail sale of cannabis. What are your views on this issue?




JEFF HOLDEN: As to the retail sales of cannabis, I am glad that it is going to be in this election cycle and am hoping that everyone will weigh in on this subject and vote your feelings, if not you have no right to complain about however it turns out. Community participation is the key for us all to work together.



LEIGH DAKIN: As a parent, a resident of Chester and a registered nurse, I do not support the petition to approve the sale of cannabis in our town. I am not convinced of the purported benefit, if any, of cannabis sales for the residents and businesses in Chester as it would have no positive impact on our town budget and would add a new burden on our public safety services.

From a parent’s perspective and with mental health concerns, I would not want the sale of marijuana sanctioned in Chester.  Such availability has a greater likelihood to filter the drug down to our children and to put greater stress on an already dysfunction mental health system. This decision is up to the town voters.

BEN WHALEN: Back when Colorado first took this on it was a big deal. Now it has become far more commonplace, with our neighboring states having legalized sales and having established dispensaries. My feeling is if we have the opportunity to be on the leading front of this and if the legislature sets regulations where Chester can gain income in the form of taxes, let’s do it! It’s yet another thing that will bring people to town who will then shop, stay and maybe even think about moving here. I think we will have a good idea of where the community stands on voting day and we will support and move forward with that decision.

JOHN KELLER: See answer to Question 2.





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