Westhampton has 47 miles of road and two Highway Department employees to take care of them.
That math is at the center of a growing debate at Select Board meetings, fueled by a resident’s push to widen Spruce Hill Road, neighbors’ complaints about the condition of Northwest Road and an unannounced repaving of Hooker Road.
The disputes have sparked accusations of micromanagement and questions about oversight, all while the town, after two failed overrides this year, continues to struggle financially.
Heading into fiscal 2027, the town cut one of four Highway Department positions, along with funding for road materials. The overrides would have restored the position. With another position vacant, that leaves one crew member and Superintendent Bill Jablonski, who did not respond to requests for comment for this article, left to cover every road in town.
Spruce Hill Road
The longest-running fight is over Spruce Hill Road, where a resident’s plan to build a house has stalled for more than a year amid a public back-and-forth with Select Board member Jennifer Milikowsky.
Several improvements must be made to the unpaved, town-owned road before Chris Dunn can build: it needs to be widened and stabilized to protect a stream running alongside it, and some trees must be cut.

Dunn said the project has stalled because of questions from the Select Board, mostly from Milikowsky, and he feels the road is being “singled out.” He said the same work he wants done has been completed on several other roads in town, such as Burt Road and others.
“This road for some reason has been treated differently than all the other roads in town,” Dunn said in an interview. “It seems like there’s some micromanaging that’s happening.”
Milikowsky said she wants to understand what steps must be followed to widen the road, particularly beside a stream the state considers a protected wetland resource, and how much the work would cost the town. She says neither Jablonski nor Dunn has answered those questions.
“I have yet to receive answers to either of those questions,” Milikowsky said in an interview. “If we have to do work up there, in my opinion, we have to do it legally and that could be costly.”
At a Nov. 4 Select Board meeting, Angela Panaccione of the Pioneer Valley Planning Commission said a design for the road work alone could cost more than $150,000.
Dunn had hoped the work could be covered under a bundled notice of intent, approved by the Select Board, that allows the Highway Department to do routine road maintenance throughout the year. Road widening was once included in that permit but was removed on the Conservation Commission’s guidance.
State law does not allow road widening near a wetland resource without approval from the Conservation Commission, which had not seen the bundled notice of intent until October this year, according to Chair Fred Morrison, who spoke at the Nov. 4 meeting.
Milikowsky said the town has no obligation to spend money on improvements for private development, especially with the budget as tight as it is.
She also contacted the state Department of Environmental Protection (DEP) about the stream and sought advice from town counsel on what the town must do when working next to a wetland resource. Many of Dunn’s supporters see the DEP inquiry as going over the Conservation Commission’s head.
Two Conservation Commission members at the Nov. 4 meeting, including Morrison, did not express personally that they felt Milikowsky went over their heads.
Morrison said at the meeting that all regulations need to be followed since a stream runs along Tobb and Spruce Hill roads.
“If this were a private developer trying to put a road in, that person would have to go through all the paperwork,” Morrison said. “We’re not doing this on purpose. It’s just the regulations.”
Supporters have turned out for Dunn at meetings over the past year, including John Shaw, who echoed Dunn’s criticism.
“It looks like you are micromanaging that department,” Shaw told Milikowsky.
At the Nov. 4 meeting, Dunn said Milikowsky had spent more than $3,000 of the town’s money on legal counsel, though declined to tell the Gazette where the figure came from. Milikowsky said the advice cost the town nothing.
There is still no clear path forward. Dunn said he plans to file requests for determination to the Conservation Commission to have several trees cut down, many of them dead, which could allow the road to be widened, an approach suggested at the meeting.
“For some reason, it seems like she is going to some great lengths to get these questions answered,” Dunn said.
Milikowsky said Dunn and his supporters believe the work “should just be allowed to happen.”
“It’s hard for me to imagine that doing work on a road with no homes is a responsible use of our resources and taxpayer dollars,” she said.
Hooker, Northwest roads
If Spruce Hill is a fight over whether the town should improve a road, Northwest and Hooker roads have raised a different question: why people who live on Northwest Road were told their road was too expensive to fix only to later learn that Hooker had just been paved.

Several Northwest Road residents have complained to the Select Board about the road’s condition, including Carol Klyman, who has lived there for almost 40 years. She wants lines to be painted in the middle and on the sides and expressed concern about the edges of the roadway.
“This is a liability issue. That road is not safe,” Klyman said at the board’s Oct. 20 meeting, while also detailing a time she “totaled” her car driving on the road due to the conditions.
In a letter read at that meeting, Jablonski said he understands residents’ frustration and that the road is not up to his standards. But fixing it would mean repaving and striping all four miles, at a cost of more than $8 million, Jablonski said.
At the Nov. 4 meeting, Klyman pointed out that Hooker Road had recently been paved, between the Oct. 20 and the latest meeting. Milikowsky questioned Jablonski on why the board hadn’t been told.
“It was embarrassing … after telling these folks and others who were here about Northwest Road that we couldn’t fix their road because it’s too expensive, then to find out three days later that Hooker Road was paved which we were not aware of happening,” Milikowsky said.

Jablonski said at the meeting that it was brought to his attention that Hooker Road was encroaching on private property in 2024, and that he had notified the Select Board of the issue.
He said a landowner on the road told him there were plans from 1990 to fix the road “somewhere in your office.” He found those plans, and authorized paving the road. He told the board that planned to seek about $66,000 in reimbursement in Chapter 90 state road funding for the work.
Town Administrator Patrick Grigsby declined to comment, including whether money was spend on legal counsel regarding the Spruce Hill Road debate and if he received notification that Hooker Road was being paved.
Finance Committee member Steve Holt said that given Westhampton’s finances, there isn’t enough money to keep every road up to every resident’s standards.
More roads have been paved over the years, adding to the Highway Department’s workload and the cost of upkeep, he said. Over that same time, boards and committees have tightened their oversight of town projects.
“I think the rules that everybody is following, they are following them closer than they have in the past,” Holt said. “I think everybody’s trying to do the best they can for the titles they are carrying.”
