Easthampton is one of three western Massachusetts cities, along with Agawam and North Adams, with open mayoral races on Tuesday.
The incumbent mayors have opted not to seek re-election.
The two candidates in Easthampton couldn't be more different in experience and style. Let's start with Joy Winnie.
"I was elected as city councilor in 1996 and during those 21 years, I've run unopposed 9 times," Winnie said in a recent debate on WWLP TV.
Along with those two decades on the City Council, Winnie has deep family roots in Easthampton. She's a former school bus driver who now oversees all school transportation in neighboring Northampton.
Her opponent is Nicole LaChapelle, a former member of the city's zoning appeals board, state Democratic Party official and an attorney.
"Representing workers everyday, in and out, and before that I led the Center for School Crisis as director," LaChapelle said.
The incumbent mayor, Karen Cadieux, who decided not to seek a third term, has endorsed Winnie. LaChapelle has tried to paint Winnie as an unquestioning follower of the mayor.
"Please share with me one occasion where you disagreed with Mayor Cadieux, and what you would have done differently as mayor?" La Chapelle asked in the debate.
It took a few seconds, but Winnie replied.
"One instance where I may have disagreed with Mayor Cadieux but we ended up coming to a full agreement was an instance when we first started talking about one of our contentious budgets."
Winnie did not offer any specifics on the disagreement, but said it ended amicably.
For her part, Winnie portrays LaChapelle as disconnected from Easthampton, shrugging at her support from outside progressive groups.
"The election should be won on people's experience, their vision and...how much they've participated in their communities over the years that they've lived in them," Winnie said.
Winnie trails well behind in campaign money, with the bulk of her roughly $11,600 raised this year from donors in Eastampton. LaChapelle has pulled in $34,600, with many donations coming from residents of other Massachusetts cities and towns.
This election comes while Easthampton tries to nurture an arts community in old mill buildings, with new restaurants and breweries. And also as it grapples with division among longtime and newer residents.
There've been contentious City Council meetings on whether to become a so-called sanctuary city. Winnie said it's not necessary, because the police don't work working with immigration officials anyway.
LaChapelle said the debate should continue, but didn't take a firm position.
"The issue of sanctuary cities in Easthampton is one that's very complex," she said.
Another controversy this past year was sparked by racist social media messages at Easthampton High School and students displaying the Confederate flag. The state attorney general faulted the school's response, and found students of color were disciplined at higher rates compared to white students, and with harsher consequences.
The district signed a deal with the attorney general to resolve the complaints -- a deal the new mayor will be responsible for making sure is followed.