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Mayoral election in Annapolis, Maryland (2025)
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Municipal • How to run for office |
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← 2021
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| 2025 Annapolis elections |
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| Election dates |
| Filing deadline: July 28, 2025 & October 29, 2025 (write-in) |
| Primary election: September 16, 2025 General election: November 4, 2025 |
| Election stats |
| Offices up: Mayor |
| Total seats up: 1 (click here for other city elections) |
| Other municipal elections |
| U.S. municipal elections, 2025 |
The city of Annapolis, Maryland, is holding a general election for mayor on November 4, 2025. A primary is scheduled for September 16, 2025. The regular candidate filing deadline for this election was July 28, 2025, and the write-in candidate filing deadline is October 29, 2025.
As of 2025, Annapolis has term limits for the position of mayor. Mayors can serve two consecutive four-year terms and can run again after a four year break.
Ballotpedia comprehensively covers the 100 largest cities in the United States by population. Our coverage also includes mayors, city councils, and district attorneys in the 32 state capitals that are not already part of our largest cities coverage. Please note that there may be more offices on the ballot in this capital city than what is listed on this page.
Elections
Click on the tabs below to show more information about those topics.
Candidates and results
General election
The candidate list in this election may not be complete.
The primary will occur on September 16, 2025. The general election will occur on November 4, 2025. Additional general election candidates will be added here following the primary.
General election for Mayor of Annapolis
Bob O'Shea is running in the general election for Mayor of Annapolis on November 4, 2025.
Candidate | ||
 | Bob O'Shea (R)  | |
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| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Democratic primary election
Democratic primary for Mayor of Annapolis
Jared Littmann and Rhonda Pindell Charles are running in the Democratic primary for Mayor of Annapolis on September 16, 2025.
Candidate | ||
| Jared Littmann | ||
 | Rhonda Pindell Charles | |
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| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Republican primary election
The Republican primary election was canceled. Bob O'Shea advanced from the Republican primary for Mayor of Annapolis.
Additional elections on the ballot
- See also: Maryland elections, 2025
September 16, 2025
November 4, 2025
Ballotpedia's Candidate Connection survey responses
Ballotpedia asks all federal, state, and local candidates to complete a survey and share what motivates them on political and personal levels. The section below shows responses from candidates in this race who completed Ballotpedia's Candidate Connection survey. Candidates are asked three required questions for this survey, but they may answer additional optional questions as well.
Survey responses from candidates in this race
Click on a candidate's name to visit their Ballotpedia page.
Note: Ballotpedia reserves the right to edit Candidate Connection survey responses. Any edits made by Ballotpedia will be clearly marked with [brackets] for the public. If the candidate disagrees with an edit, he or she may request the full removal of the survey response from Ballotpedia.org. Ballotpedia does not edit or correct typographical errors unless the candidate's campaign requests it.
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Bob O'Shea (R)
ANNAPOLIS Preservation:
Our city has a unique feel that makes Annapolis the place it is. That is why we are attracted to the area and tourists come to visit. Current City Administration and Officials are trying to make Annapolis another cookie cutter, overdeveloped destination that I vocally oppose. I support controlled development with a vision that makes Annapolis the Community that it is. I oppose the Spot Zoning Height Restrictions Relief that some past Zoning Individuals say IS NOT Spot Zoning.
CRIME / Safety:
Bob O'Shea (R)
Annapolis Preservation (Enforce) Crime (Reduce and Promote Abiding to our Laws) Costs of Living (Stabilize, Lower) Overstaffed City Hall (Reduce, Create Efficiencies)
Planning, Zoning, Regulations (Empower Associates)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Candidate profiles
This section includes candidate profiles that may be created in one of two ways: either the candidate completed Ballotpedia's Candidate Connection survey, or Ballotpedia staff may compile a profile based on campaign websites, advertisements, and public statements after identifying the candidate as noteworthy. For more on how we select candidates to include, click here.
Party: Republican Party
Incumbent: No
Political Office: None
Submitted Biography: "My name is Bobby O’Shea, and I am seeking your vote for the Mayor of Annapolis on the 11/2025 election. I grew up in Canandaigua, a small waterfront town in upstate New York. Canandaigua, in Seneca, means “The Chosen Spot.” I fell in love with the waterman’s way of life boating on Finger Lakes and fishing off the city pier. My mom and dad, Diana and Bob, taught me to love and respect native cultures and heritage. I am passionate about preserving history truthfully, no matter how painful it may be. In 2000, I chose Annapolis as my home because of its beauty, diverse history, and the Chesapeake Bay. My son, Trey, and I reside in Murray Hill. The ‘man’ in charge of our home is Togo, our faithful dog. Another important part of our family are the seven midshipmen we have sponsored. I was a member of the Board of Trustees for the Naval Academy Primary School. To this day I enjoy attending events at the ‘Little White Schoolhouse’ on Greenbury Point. I understand the key to success is a good education. As mayor I will work with the county and local non-profits to ensure our schools have all the resources they need, so every child thrives. I am running to be the next mayor of Annapolis because of the love and passion I have for this place we call home. Annapolis is the eight unique wards with their own distinct character and history. I want your vote so together we can make Annapolis the city she was always meant to be. This will promote Transparency, Accountability, Accessibility !"
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Mayoral partisanship
Annapolis has a Democratic mayor. As of September 2025, the mayors of 35 state capitals are affiliated with the Democratic Party, seven are Republicans, one is independent, and two are nonpartisan. The partisan affiliation of five state capital mayors is unknown. While most mayoral elections in state capital cities are nonpartisan, most officeholders are affiliated with a political party.
Help inform our readers
Take our candidate survey
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We ask all federal, state, and local candidates to complete a survey and share what motivates them on political and personal levels. Our survey helps voters better understand how their candidates think about the world and how they intend to govern—information they need to feel confident they're picking the best person for the role.
If you are a candidate, take our survey here. Or you can ask a candidate to take the survey by sharing the link with them.
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About the city
- See also: Annapolis, Maryland
Annapolis is a city in Anne Arundel County, Maryland. As of 2020, its population was 40,812.
City government
- See also: Mayor-council government and Council-manager government
The city of Annapolis utilizes a council-manager system combined with a strong mayor. In this form of municipal government, the city council serves as the city's primary legislative body and the mayor serves as the city's chief executive. The mayor, however, appoints a city manager to oversee the city's day-to-day operations and execute city policies.[1]
Demographics
The following table displays demographic data provided by the United States Census Bureau.
| Demographic Data for Annapolis, Maryland | ||
|---|---|---|
| Annapolis | Maryland | |
| Population | 40,812 | 6,177,224 |
| Land area (sq mi) | 7 | 9,711 |
| Race and ethnicity** | ||
| White | 61.2% | 54.2% |
| Black/African American | 21% | 29.9% |
| Asian | 2.1% | 6.4% |
| Native American | 0.1% | 0.3% |
| Pacific Islander | 0% | 0% |
| Other (single race) | N/A | 4.7% |
| Multiple | 3.6% | 4.5% |
| Hispanic/Latino | 20.1% | 10.3% |
| Education | ||
| High school graduation rate | 88.8% | 90.6% |
| College graduation rate | 50% | 40.9% |
| Income | ||
| Median household income | $87,897 | $87,063 |
| Persons below poverty level | 10.1% | 9% |
| Source: population provided by U.S. Census Bureau, "Decennial Census" (2020). Other figures provided by U.S. Census Bureau, "American Community Survey" (5-year estimates 2015-2020). | ||
| **Note: Percentages for race and ethnicity may add up to more than 100 percent because respondents may report more than one race and the Hispanic/Latino ethnicity may be selected in conjunction with any race. Read more about race and ethnicity in the census here. | ||
See also
| Annapolis, Maryland | Maryland | Municipal government | Other local coverage |
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External links
Footnotes
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