Democratic Challenger, Dr. David Chess, speaking outside the Baldwin Center in Stratford on Wednesday, October 29th, 2025. Credit to Jim Shannon/Hearst Connecticut Media
Table of Contents
Overview
And…..just like that, it’s almost Election Day! Though there is no presidential race or statewide contests this year. Almost every town in Connecticut is holding local elections for powerful positions of authority, such as Mayors, Selectmen, Town Councils, and Boards.
National pundits are paying attention to the off-year gubernatorial races in Virginia and New Jersey. People want a sense of the political environment in the first year of President Donald Trump’s second term. Sometimes, this allows for clues and a possibility of what to expect as we dive into midterms next year.
In addition, Democrats are looking for a way out after being locked out of power in Washington, D.C., post-2024 elections. The idea is that backlash against Donald Trump can help them win in cities and towns across the country. In addition, the Democratic Party is split into factions arguing about how to guide strategies across the country; some hope elections on Tuesday will give some hints on the issues to focus on.
Republicans are hoping to rack up wins after a great 2024 cycle. Though President Trump has lost support on economic and immigration polices, Republicans hope the gains they made with voters of color and young men can hold true in an off-year election, especially as some communities have moved rapidly to the right in the Trump era. This change allows multiple opportunities in local races across the country.
The Connecticut Environment
Connecticut is known for its split-ticket tendencies in local races. Though Democrats dominate federal races in the state in recent decades, Republicans hold several offices in towns Democrats win on the federal level.
In an article from the Hartford Courant, Democrats are expecting to hold seats for mayor in Stamford, Newington, and Danbury, as well as First Selectman in Litchfield and Colchester. They also expect to hold town council majorities in Wethersfield and Coventry.
Republicans, according to Connecticut Republican Party Chair Ben Proto, expect to do well in Torrington, Wallingford, Brookfield, East Haven, Fairfield, Old Lyme, East Lyme, East Hartford, and Danbury.
In an effort to win over voters, Democrats have been tying Republicans to Trump, whose approval rating has dropped throughout the year. Republicans have argued that voters are focused on local issues and that national politics doesn’t play a role in the day-to-day operations of cities and towns.
Many cities have competitive races. Though I can’t cover all of them here, I would love to highlight a few for readers to take a look at. Let’s Dive In!
Danbury
2023 Race
In 2023, Democrats dramatically shifted political power in Connecticut’s largest swing city, Danbury.
Led by Democrat Roberto Alves, who won the mayoral race in a rematch, Democrats flipped five at-large seats and eleven ward seats. Democrats won the mayoral race in Danbury for the first time in two decades.
Alves lost narrowly in 2021 against former Republican mayor Dean Esposito by two points 49-51. Alves won a rematch in 2023 against Esposito in a similarly close 51-49 victory.
2025 Campaign
Incumbent mayor Alves is running for a second term against Republican City Councilman Emile Buzaid Jr.
Though Alves has outraised Esposito by a large margin, holding a $260,000 advantage three weeks prior to the election, another close race is expected in the most competitive race of the state’s largest cities.
Alves has risen as a statewide figure in his short tenure. Governor Ned Lamont tapped Alves as the chair of the Connecticut Democratic Party after the 2024 elections. Alves succeeded Party Chair Nancy DiNardo, who was expected to step down in January 2025.
Lamont was showing City Democrats that he is paying attention to the Democrats’ issue of a drop in the urban vote. He showed he would invest in the party’s infrastructure, tapping the mayor of a diverse city. Lamont said Alves knew the party structure well and liked him as a mayor and an executive with business experience.
During the campaign, Alves has promoted his bipartisan work and how he prioritizes listening to all voices in the community. Alves announced in September that he has Large B-Cell lymphoma, but said he continues to take his responsibilities seriously and said the prognosis was good.
Buzaid Jr. says Alves has failed to improve the city as taxes keep rising under his watch. His campaign is also focusing on creating a Department of Economic Development. This would restore rail service to NYC, promote workforce development, and have a budget to maintain fund balance and credit rating. Alves pointed to millions in infrastructure improvements and bringing the city back from financial collapse.
Alves is favored for re-election due to his new position and his fundraising advantage. Buzaid can put up a good fight due to the City’s political lean, which was a 53-46 margin for Vice President Kamala Harris last year.
Stratford
Democratic Primary
Stratford had a Democratic Primary on September 9th, where Physician David Chess won in an overwhelming 87-13 landslide over Businesswoman Linda Manos. It was the largest victory of the night.
Chess had the overwhelming support of the Democratic Town Committee, along with local politicians.
2025 Race
Republican Incumbent Laura Hoydick has found herself in a tough re-election campaign for a third term against Democratic challenger David Chess
Hoydick won in a landslide in 2021 for her second term, winning 63-37.
Hoydick has been popular while in office. A state representative before she won the mayoral race in a 50-44 victory against her Democratic challenger in 2017. Hoydick has routinely run over the federal lean of the town.
Stratford voted for Kamala Harris by a large 59-40 margin last year. A Trump presidency is bringing out Democrats, making this a competitive race. Many of them may be voting due to the national mood, as a protest against the President. Due to this, Hoydick might see a closer result, similar to the 2017 race. Either way, everyone in town is taking the race seriously. Stratford has led the state in early voting so far with 3535 voters! (As of Thursday)
Main Issues Facing Voters
The police and fire unions both endorsed the challenger Chess. The complaints they have are about pension benefits, as affordability ranks as a top issue in the race. Chess also received the endorsement from 3rd District Congresswoman Rep. Rosa DeLauro
Stratford taxes are also among the highest in the state. The Publication Only in Bridgeport discusses an expected reevaluation of properties expected in 2026. In addition, they also discuss that a poor economic future is predicted due to limited tax growth.
In a recent debate, Hoydick argued that she has been a stabilizing and unifying leader of the shoreline community. She also said that she loves her job, and explained how remarkable the town is. Chess said he wasn’t planning to run for mayor, but explained he felt the town has been squandered due to its economic development.
Chess also advocated for an independent finance committee, disagreed about the development of a 154-unit housing complex, and took issue with council-approved plans to develop Riverside Park. Hoydick defended her tenure, explaining that taxes had not risen during her tenure and said the council’s plans made sense.
When Chess had complaints about education, Hoydick noted that she doesn’t have control over the school district, as the elected school board oversees that.
Chess and Hoydick did agree on protecting the town’s natural beauty and environment. In addition, they were both open to finding more sites for residents to play Pickleball.
What to Expect on Tuesday
This is a difficult race to predict. A town at the local level that is open to voting for Republicans, but backs Democrats solidly at the federal level. It will come down to turnout. If Democrats come out at high turnout, motivated by Republican control nationally, then Chess will win. If enough Democrats continue to cross over and vote for Hoydick, she’ll make it to a 3rd term.
I’m leaning Hoydick, who has long outrun the federal toplines in the town. However, I would not be surprised if Chess wins on Tuesday.
Milford
2025 Race
Milford is a true 50/50 town. Kamala Harris won the town by a mere 0.55% , 47.3-46.7.
Incumbent Mayor Tony Giannattasio is facing former mayor Rich Smith. Smith was appointed in 2023 to succeed Mayor Ben Blake, who resigned to take a job as an administrative law judge. Smith did not run in 2023.
Giannattasio won his first term in November 2023, defeating Democrat Kerri Rowland 52-48.
Smith not running for the top post in 2023, Democrats say, might have cost them the mayorship. Smith, though, came around and realized how much he enjoyed his time in the mayor’s change and started planning a comeback. He has been a longtime staple in Milford Democratic politics, serving as the DTC chair for years and as chair of the police commission.
Smith and Giannattasio have argued about the reasons for tax increases. Smith says he’ll keep them lower than the mayor’s GOP budgets, but Giannattasio says it’s lower than Smith calculated, and it’s covering costs ignored by the previous administration.
Gianntassio says he is focused on the economic growth of Milford, establishing 55+ housing, and properly funding city departments. He said his increase of funding for Milford’s police and fire departments, and the sale of city-owned properties, have helped the town.
Smith says he will drive down tax increases and stabilize the city’s economy. He says his private sector experience will help him manage the budget better to cut costs efficiently.
Recent History of Mayoral Races
Milford, like many towns in the state, finds it very difficult to dislodge an incumbent mayor. Though President Joe Biden won a larger 55-44 victory in 2020, Democrat Mayor Ben Blake won a massive 69-31 victory in 2021 and a 67-33 victory in 2019. The town then flipped to Republican Giannattasio 52-48 when Blake did not run again.
Similarly, in 2009, Incumbent Republican Mayor James Richtelli Jr won a large 60-27 victory for a 5th term. He did not run again in 2011, and Blake flipped the town back 56-42 against Republican Bernard Joy.
Two things could happen: Giannattasio wins a 2nd term, like many of his predecessors, or Smith pulls an upset, and a result similar to the federal toplines would occur.
I am leaning towards Giannattasio, though I don’t think the margin would be as large. However, I would be surprised if Smith pulls an upset, based on the history of Milford elections, as it seems they generally re-elect their incumbents. Smith, though, might have a unique opening as someone who served as mayor for a few months. Also in 2016, Hillary Clinton won a similar margin to Kamala Harris in the town of Milford, winning by a mere 0.8%, suggesting that the town’s shift to the right from 2020 isn’t a permanent change, and voters clearly are willing to vote for either party.
Newtown
2025 Race
Republican incumbent First Selectman Jeff Capeci is running for a second term against Democrat Bruce Walczak. Walczak is also running on the Independent Party ballot line.
Their running mates for Selectman, Capeci, is running with Republican Charlie Gardner. Walczak is running with Democrat Paul Lundquist.
Capeci was the leading Republican who chaired the town’s legislative council prior to his election as First Selectman. Capeci has served in a variety of elected roles, including the Board of Selectmen and the Charter Revision Committee. He has a background in engineering career manufacturing software development.
Capeci, a 29-year resident of Newtown, says he will focus on maintaining fiscal responsibility and transparency by expanding Newtown’s commercial and industrial grand list through smart, sustainable development. Capeci mentions the revitalizations of Fairfield Hills, preserving Newtown’s rural charm, enhancing public safety, and infrastructure.
Walczak is a businessman and entrepreneur. Walczak cites his business experience on his website, supervising teams of 250+ employees, as a reason why he can manage Newtown’s $40 million budget. He has served as an elected member of the Newtown Police Commission and other boards, such as the Business Advisory Commission and the Economic Development Commission.
Walczak, a 34-year resident of Newtown, says he is running because he cares deeply about the town and the people. Walczak is also running on being “laser-focused” on the few things that matter to every resident, such as budgets, infrastructure, schools ,and smart development. He cites the Republicans’ board not being focused and looking at book bans instead.
Prior Mayoral Races and Political Environment
Walczak, notably, was on the ballot for First Selectman all the way back in 2009 as an Independent Candidate. He got 27.7% of the vote, splitting the vote with Democrat Gary Fetzer. Republican Mayor Patricia Llodea won re-election.
I thought this race could be competitive, as in the 2023 open race for First Selectman, Capeci won by 123 votes, in a close 51-49 victory against Democrat Dan Cruson. This was also the first contested race in Newtown since 2017.
Newtown voted 54-44 for Kamala Harris in the 2024 presidential election.
Though Walczak has run as an independent multiple times with limited success, being on both the Democratic and Independent ballot lines can bring him some appeal. I think the 2023 narrow victory for Capeci makes him vulnerable, but he is the incumbent now. This race has not gotten as much media coverage as other local races, meaning maybe Capeci is seen as more favored than the toplines suggest, but we will have to see what happens.
Brookfield
2025 Race
Democratic incumbent First Selectman Steve Dunn is running for a non-consecutive fifth term in the town of Brookfield. He is running alongside Democratic incumbent Bob Belden.
Dunn is facing off against Republican Karl Hinger. Hinger is running alongside Republican Alan Donnelly for the position of Selectman.
Hinger mentioned during his nomination at the Republican caucus, his top issues are cutting back on overdevelopment and large-scale multifamily housing. He is also focused on fiscal responsibility to be “smarter without debt“. Hinger has been a member of Brookfield’s Zoning Board of Appeals since 2021.
Dunn’s Non-Consecutive Terms in Office
Dunn was Brookfield’s First Selectman from 2015 to 2021. In 2019 and 2021, he won by large margins. He won 63-37 in 2017 and 56-44 in 2019.
Dunn, however, was knocked out of the town’s top position in 2021, where he lost 47-51 against US Army Veteran Republican Tara Carr. Carr won and was determined to bring Brookfield’s historical Republican roots by keeping taxes low, supporting education, and small business.
Carr’s tenure did not long as First Selectwoman. Dunn won his job back as First Selectman in 2023, winning comfortably 54-46.
This is one of the towns that Trump carried last year in the Presidential election, where Democrats hold the top position in the town. Trump won 51-47.
Due to the back-and-forth change of party control, I expect a close race in this Trump town. However, I think Dunn can win a 5th term as he will benefit from increased Democratic turnout similar to 2023 and 2017. Dunn has proven, though, that incumbents who won by comfortable margins two years prior, however, aren’t safe. So like every other race on the docket, an upset can’t be ruled out.
We will see what happens!
East Granby
2025 Race
Finally, the town of East Granby.
Republican Selectwoman Eden Wimpfheimer is running for a third term against Democratic challenger Jason Hayes.
Hayes is leading a 17-candidate Democratic slate heading into Tuesday’s election, where Democrats have a candidate for every office on the ballot. Wimpfheimer is running alongside Republican Todd Zessin. Hayes is running alongside Democrat Amanda Thompson for Selectman.
Wimpfheimer, a 25-year resident, previously served on the town’s select board. In addition, she works as a realtor since 1999 with Berkshire Hathaway.
Wimpfheimer is running on town progress by revitalizing infrastructure, supporting local business growth, and making East Granby an attractive place to live.
Hayes is running on issues that affect the town’s safety and financial well-being, according to his website. This includes questionable land sales to family and former business associates, the deficit in the town’s general fund due to years of inaction, and examples of financial liability to the town itself.
Hayes’s background is not in politics. He has spent 30 years working as a Celebrity Wig Artist, working with networks like CBS, NBC, and Netflix. Before his career, he worked in the insurance industry. Hayes believes that the town’s well-being is not being represented or protected under the current Selectwoman Wimpfheimer.
This race is expected to be very close. Wimpfheimer has won by identical 52-48 majorities in both 2021 and 2023. Prior to Wimpfheimer’s 2021 victory, Democrat First Selectman James Hayden won a large 60-40 victory in 2019. Wimpfheimer has performed close to the federal topline in this election, with no increase after her 2021 victory. Kamala Harris won East Granby 52-46 last year.
Local Democrats Coming to Campaign
Democrats, sensing an opportunity, have been pulling out all the stops to help bring Hayes over the top. Some of the biggest names in the state, including Senator Chris Murphy, Lieutenant Governor Susan Bysiewicz, former Hartford Mayor Luke Bronin, and State Rep. Jillian Gilchrest, have been campaigning alongside Hayes.
Hayes has been open about his dislike of Donald Trump and the MAGA movement, saying he’s not apologizing for those beliefs as a gay candidate. Hayes, who moved into the community with his husband, continued to get more involved; he wanted the top spot in the town.
Incumbent Wimpfheimer has been focused on her record, which includes an increase of the grandlist, a new town manager, an affordable housing plan, and revitalizing infrastructure. She also cited her dislike of negative campaigning, saying I have nothing to say about my opponent.
Wimpfheimer said she focuses on local government when asked how she feels about President Trump.
Hayes seems to be attracting some energy for his campaign, not only bringing out notable state Democrats, but a fiery speech talking about how he would battle Republicans and his outfit while campaigning with a leather motorcycle jacket, brown boots, and jeans, not looking like a typical politician.
Bronin marked how Hayes is not afraid to go everywhere, and how he has a lot of energy.
What to Expect on Tuesday
An incumbent like Wimpfheimer is difficult to knock out. She seems not to be focused on MAGA politics, but the governing of the town. That can help her stay ahead in a Harris +6 town. However, she has had two consecutive narrow victories, and this race seems to have attracted more attention.
Currently, I’m leaning towards Hayes for an upset against Wimpfheimer. East Granby has had, as the Hartford Courant describes it, a “mixed voting history”. It has voted for Democrats on the presidential level in 2016, 2020, and 2024. Though Wimpfheimer has won two terms as a Republican, Democrats controlled the First Selectman position for 25 years. At the same time, Republicans have dominated races in the state legislature. It’s a close race, but local dynamics and turnout will play a large role in this race, which makes me lean toward Hayes, due to an expected increase in Democratic turnout, but it will be close.
Conclusion
I want to be clear, there are way more competitive races in the state than I could write about myself.
But this is just a few I wanted to bring to your attention. Some races I mentioned may not end up being competitive. But some towns, I think, will be competitive. It’s hard to say what’s going to happen in certain towns and cities; sometimes turnout is not what is expected, or a town breaks a long-running pattern. However, it’s all very exciting.
There could be multiple upsets, surprise victories, and unexpected results. I’m excited to see what unfolds on election day!
Anything can happen.
Thanks for Reading!