The longtime mayor of Orange County's largest city is facing a primary challenge later this month.

Incumbent Middletown Mayor Joe DeStefano will face off against Orange County legislator Joel Sierra.

DeStefano was elected city mayor in 1993 and served until 2005. He was reelected in 2009 and has won every race since then.

Sierra is an 8-year Orange County legislator who currently represents the 20th District.

DeStefano said he's focused on reducing crime, increasing economic development and expanding recreational opportunities in the city.

"I've probably been one of the most vocal people in the Hudson Valley as a Democrat the past several years, especially since Trump came on the scene, in opposing the Trump agenda and I've been very outspoken," DeStefano said.

Sierra faced public pressure to step down earlier this year, after missing nearly every legislative meeting for the past three years despite collecting a full salary and benefits. Sierra was a full-time firefighter in Middletown when he was hurt on the job in 2022, which he claims prevented him from showing up in person. He said that while he didn’t attend legislative meetings in person, he was patched in virtually and remained in communication with leaders and constituents.

In March, he told News 12, "he'd show up for the job if elected as Middletown Mayor."

He did not respond to multiple requests for an interview ahead of this primary election.

According to his campaign website, he's running to implement term limits for mayors, offer more incentives for affordable housing and provide more transparency in contract bidding.

There are two other primary races in Middletown and both involve Democrats running for city alderman positions.

Incumbents Katie Wray and Paul Johnson are running for re-election for two seats in the third ward, along with Roberto Browne and Rafael Cordero.

Incumbents Jude Jean-Francois and challengers Alex Rodriguez and Evelyn Ortega are all running for two seats in the fourth ward. Longtime alderman Sparrow Tobin previously announced his intention to retire at the end of this term.

The Middletown Democratic Committee endorsed DeStefano for mayor as well as Wray, Johnson, Jean-Francois and Rodriguez for alderman.