2021 Stamford mayoral election
The 2021 Stamford mayoral election was held on November 2, 2021. Incumbent Democratic mayor David Martin sought re-election to a third term in office, but lost renomination to state representative Caroline Simmons. Simmons, who was also endorsed by the Independent Party, faced unaffiliated candidate Bobby Valentine. Initial results indicated Simmons had a slight lead over Valentine. Absentee ballots swung heavily in Simmons' favor resulting in a 5-point lead over Valentine. Simmons will be Stamford's first female mayor. Democratic primary. On July 25, the Stamford City Committee narrowly voted to endorse Simmons over the  incumbent Martin, with 21 members voting for Simmons and 19 voting for Martin. Shortly thereafter, Martin declared his intention to continue with his candidacy and force a primary. According to the Connecticut Secretary of State, Martin was required to collect 1,550 signatures, 5 percent of the total number of registered Democrats in the city. Martin collected over 3,000 signatures, guaranteeing a Democratic Primary. The primary was held on September 14. The ballot also included elections for the Stamford Board of Representative District 5, and Stamford Board of Representative District 19. Simmons won in a landslide, earning a majority of support  in all of city's 20 voting districts. Martin conceded the night of the primary and endorsed Simmons. Republican endorsement. The Republican Stamford City Committee endorsed Joe Corsello as its mayoral candidate. However, he withdrew from the race on September 8 and endorsed Bobby Valentine. Independent endorsement. The Independent Party of Connecticut endorsed Caroline Simmons for mayor in August 2021.