Boston is set to make history with this year’s mayoral election. Voters can now mail in ballots, vote early or wait for the ritual of voting on Election Day, Tuesday, Nov. 2. Whether City Councilor Michelle Wu or Annissa Essaibi George, both Democrats, come out on top in the general election, the city will have a woman of color leading it for the first time.

Voters will also cast ballots for four at-large seats on the City Council in addition to several district seats and three ballot questions.

Here’s what you need to know.

Key Dates

Saturday, Oct. 23 - Friday, Oct. 29: Early voting period
Wednesday, Oct. 27: Deadline to apply for a mail-in ballot
Tuesday, Nov. 2: Election Day

When Is The 2021 Boston Mayoral Election?

Boston’s general municipal election takes place on Tuesday, Nov. 2, where voters will cast ballots for mayor and City Council. You can check your voter status here.

How And Where To Vote

If you plan to vote in person on election day, polls are open from 7 a.m. to 8 p.m. Use this form to find your polling location

This year, any voter in Boston will be allowed to vote by mail. To apply, fill out this form and either mail it or drop it off at City Hall. If you are going to mail your ballot, make sure to give yourself enough time: the U.S. Postal Service recommends allowing seven days for the trip. The deadline to apply to vote by mail is Wednesday, Oct. 27.

You can also plan to drop your ballot off in any of the drop boxes around the city — available now through 8 p.m. on Election Day.

Boston has launched an Accessible Electronic Voting System for residents with disabilities to vote electronically.

Take a look at some of voting rights for Massachusetts residents.

How And When To Vote Early

Any registered Boston voter can choose to vote early at any early polling location if they wish.

The early voting period runs from Saturday, Oct. 23 to Friday, Oct. 29. Find an early voting location here.

Although there are locations across the city, City Hall is the main location for early voting. It’s open from 11 a.m. to 7 p.m. on Saturday, Sunday and Monday; 9 a.m. to 8 p.m. on Tuesday and Thursday; and 9 a.m. to 5 p.m. on Wednesday and Friday.

What Are The Ballot Questions?

Boston voters will vote on three questions, one binding and two non-binding. A non-binding resolution provides advisement for public officials; it would need approval from the City Council, mayor and governor to go into effect.

Question 1, a binding question, concerns the budget process for the City Council. A “yes” vote would shift budget power away from the mayor, giving the Council more authority to veto the mayor’s budget and amend it. If passed, residents would have more input on how the city spends money through a newly-created Office of Participatory Budgeting.

Question 2 is non-binding and asks voters whether an Eversource electric substation should be built along the Chelsea Creek in East Boston rather than a different nearby location.

Question 3 is non-binding and concerns whether Boston School Committee members should be elected. Currently, the mayor appoints committee members. This resolution proposes having members elected by the public. Essaibi George has said she supports keeping an appointed system with the mayor making appointments; Wu has said that she supports electing school committee members but wants some to be appointed to account for diversity and expertise. All but one of the City Council candidates expressed support for a hybrid or elected school committee; Erin Murphy said she was awaiting the results of the ballot question.

Who Are The Candidates For Mayor?

Annissa Essaibi George has been an at-large City Councilor since 2016 and was previously a Boston Public Schools teacher for 13 years. A longtime Dorchester resident, she has stood out for rejecting calls to reallocate police funding and is the leading candidate for public safety unions. She has campaigned as the slightly more moderate candidate and a successor to former mayor Marty Walsh’s legacy.

Michelle Wu has led in the polls since she jumped into the race over a year ago. A Chicago native who has lived in Boston since she got her law and undergraduate degree at Harvard, Wu has been an at-large City Councilor since 2014. She has positioned herself as a candidate who will fight for bold progressive policies aimed at systemic change. She has picked up notable endorsements from progressive groups and local officials, including Acting Mayor Kim Janey and Sen. Elizabeth Warren.

Where Do The Candidates Stand On The Issues?

Mass & Cass: Both Essaibi George and Wu say services need to be decentralized to address the homelessness and addiction crisis at the intersection of Massachusetts Avenue and Melnea Cass Avenue.

The candidates sparred Monday evening in a final debate over Mass and Cass and a recovery center on Long Island. Both candidates said they do not support Sheriff Steve Tompkins’ plan to house Mass and Cass residents involuntarily in the South Bay Correctional Facility. Essaibi George stood firmly in favor of a plan to build a bridge to the Long Island campus, while Wu backed re-activating a ferry shuttle. Wu said she doesn't believe the plan to rebuild the bridge is a short-term solution.

Police: Perhaps the issue that the candidates differ most on, Essaibi George has consistently rejected calls for reallocating police funding and has said that the city should hire more police officers. She told BPR she supports enacting the reforms recommended by the police reform task force. And she advocates placing mental health officers in stations to respond to non-criminal crises.

Wu has advocated for more investment in public safety overall and has called for a public health approach to replace some work done by police officers, for example having mental health counselors respond to crisis situations.

Housing: Essaibi George said the city should increase its housing supply and focus on affordable family housing, adding that, within her first 100 days in office, she would increase funding for the city’s support for homebuyers. Michelle Wu has been a vocal advocate of rent control, which would require action from the state Legislature, and supports a plan to cap rent increases while also creating opportunities to drive new construction.

Environment: Essaibi George says that climate solutions should take a “neighborhood-centered” approach rather than relying on stakeholders outside the city. She would plan to improve green infrastructure and invest in green urban spaces and parks in low-income neighborhoods.

Michelle Wu released her plan, “Boston’s Green New Deal,” early in the race, which includes approaches such as making the deadline for the city’s decarbonization earlier, increasing the city’s tree canopy and infrastructure-based solutions like a fare-free T.

Read more about the candidates’ stances on key issues.

Who Are The Candidates For At-Large City Council?

There are eight candidates in the race for four at-large seats on the City Council, down from 17 in the preliminary election.

Michael Flaherty is an incumbent who was first elected in 2000, previously working as an Assistant District Attorney in Suffolk County. He lives in South Boston and has made affordable housing central to his campaign. Rep. Stephen Lynch and Suffolk County Sheriff Steve Tompkins have endorsed him.

Althea Garrison replaced Ayanna Pressley on the Council after Pressley became a Congresswoman in 2018, and has run several times in the past. She told GBH News she is against cutting funds from the police department budget and supports hiring more officers.

David Halbert is a former staffer for Gov. Deval Patrick who lives in Dorchester. He told GBH News that he supports the city adopting a Green New Deal, and that he supports redirecting police department funds to hiring more mental health clinicians and social workers to address public safety concerns. Rep. Ayanna Pressley, Councilor Andrea Campbell and State Sen. Sonia Chang-Díaz have endorsed him.

Ruthzee Louijeune is an attorney and activist who formerly worked on Sen. Elizabeth Warren’s campaigns and lives in Hyde Park. She supports re-directing public safety funds to increased mental health services and also to funding homeownership in low-income neighborhoods. Sen. Elizabeth Warren, Rep. Ayanna Pressley, Councilor Andrea Campbell and the Boston Teachers Union have endorsed her.

Julia Mejia is an incumbent from Dorchester who was elected in 2019 and became the first Afro-Latina councilor. She previously worked as a producer at MTV and led civic engagement groups. Rep. Ayanna Pressley, Councilor Andrea Campbell, State Sen. Sonia Chang-Díaz and Sunrise Boston have endorsed her.

Carla B. Monteiro is a social worker from Dorchester who has said her focus would be climate change, transportation and affordable housing if elected. Rep. Ayanna Pressley, Councilor Andrea Campbell and Sunrise Boston have endorsed her.

Erin Murphy is a Boston Public Schools kindergarten teacher from Dorchester who previously ran for the council in 2019. Education has been the central issue of her campaign and she told GBH News the Boston Police Department needs to hire more officers, not fewer. Boston EMS, Boston Police Patrolmen’s Association and City Councilor Frank Baker have endorsed her.

Bridget Nee-Walsh is an iron worker and business owner from South Boston. She told GBH News the city should increase funding for police officer hiring and training, and that the city should return to the community policing model from Mayor Tom Menino’s tenure. City Councilor Frank Baker, State Rep. Dan Ryan and Boston Police Patrolman’s Association have endorsed her.

Learn more about the City Council candidates.

Stay up-to-date on the latest campaign news here and follow GBH News’ politics team on Twitter: @Kadzis, @reillyadam and @SWINTERSMITH.

This story has been updated to include the candidates' debate about Mass and Cass.