For Immediate Release:             Contact:
July 24, 2025 City of Joliet:     815-724-4000  

City of Joliet Appoints New Director of Cultural Affairs and Special Events
Veteran Leader Brings 25 Years of Experience to Joliet

JOLIET, IL — The City of Joliet is pleased to announce the appointment of Ann Sylvester as its new Director of Cultural Affairs and Special Events. With over 25 years of experience in cultural programming, large-scale event logistics, and community engagement, including serving as Deputy Commissioner of Operations and Permits for the City of Chicago’s Department of Cultural Affairs and Special Events—Sylvester brings a wealth of leadership, creativity, and operational excellence to the role.

“We’re excited to welcome Ann to the City of Joliet,” said Mayor Terry D’Arcy. “She brings not only an impressive track record in executing world-class events, but also a deep understanding of how to engage communities, foster inclusivity, and turn public spaces into cultural landmarks. Her leadership will help Joliet shine on the regional and potentially national stage.”

Throughout her tenure with the City of Chicago, Sylvester played a key role in the planning and execution of hundreds of large-scale public events, including iconic traditions such as the Chicago Air & Water Show and the Taste of Chicago, Memorial Day Commemorations, and major civic parades—serving millions of attendees annually. In recent years, she oversaw the City’s permitting division and production of more than 150 events each year, demonstrating exceptional leadership in logistics, stakeholder coordination, and public engagement. She also managed operations at Millennium Park and the Chicago Cultural Center, overseeing multimillion-dollar contracts, post-pandemic reopening strategies, and major capital improvement projects.

In addition to her operational expertise, Sylvester has played a leading role in national event planning, serving as co-chair of the Community Engagement Committee for both NASCAR’s inaugural Chicago Street Race and the 2024 Democratic National Convention. Her efforts ensured strong community partnerships and tangible benefits for local neighborhoods.

“I’m honored to join the City of Joliet during such an exciting time,” said Sylvester. “With the upcoming Centennial of Route 66 and the transformation of Downtown’s City Square into a vibrant community hub, Joliet is poised for a cultural renaissance. I’m eager to collaborate with residents, organizations, and city leaders to create inclusive, memorable experiences that celebrate the city’s unique identity and energize its future.”

Sylvester holds a Master of Science in Integrated Marketing Communications from Northwestern University and a Bachelor of Science in Business from Miami University. She has also completed leadership coursework through the Urban Park Leadership Program at the City University of New York. Her past board involvement includes the Grant Park Music Festival and Chicago Children’s Theatre.

In her new role, Sylvester will oversee the planning and coordination of community celebrations, special events, and cultural initiatives—building on Joliet’s rich history while expanding opportunities for residents and visitors alike to connect, celebrate, and be inspired.

# # #

About the City of Joliet
The City of Joliet is located in Will and Kendall counties in the State of Illinois, 30 miles (48 km) southwest of Chicago. It is the county seat of Will County. At the 2020 census, the city was the third largest in Illinois, with a population of 150,362. For more information about the city, visit https://www.joliet.gov.

Media Contact: Rosemaria DiBenedetto, Media Engagement and Communications Director, Cell: 847-269-5556 or email: rdibenedetto@joliet.gov

For Immediate Release:             Contact:
July 24, 2025 City of Joliet:     815-724-4000  

City of Joliet Appoints New Director of Cultural Affairs and Special Events
Veteran Leader Brings 25 Years of Experience to Joliet

JOLIET, IL — The City of Joliet is pleased to announce the appointment of Ann Sylvester as its new Director of Cultural Affairs and Special Events. With over 25 years of experience in cultural programming, large-scale event logistics, and community engagement, including serving as Deputy Commissioner of Operations and Permits for the City of Chicago’s Department of Cultural Affairs and Special Events—Sylvester brings a wealth of leadership, creativity, and operational excellence to the role.

“We’re excited to welcome Ann to the City of Joliet,” said Mayor Terry D’Arcy. “She brings not only an impressive track record in executing world-class events, but also a deep understanding of how to engage communities, foster inclusivity, and turn public spaces into cultural landmarks. Her leadership will help Joliet shine on the regional and potentially national stage.”

Throughout her tenure with the City of Chicago, Sylvester played a key role in the planning and execution of hundreds of large-scale public events, including iconic traditions such as the Chicago Air & Water Show and the Taste of Chicago, Memorial Day Commemorations, and major civic parades—serving millions of attendees annually. In recent years, she oversaw the City’s permitting division and production of more than 150 events each year, demonstrating exceptional leadership in logistics, stakeholder coordination, and public engagement. She also managed operations at Millennium Park and the Chicago Cultural Center, overseeing multimillion-dollar contracts, post-pandemic reopening strategies, and major capital improvement projects.

In addition to her operational expertise, Sylvester has played a leading role in national event planning, serving as co-chair of the Community Engagement Committee for both NASCAR’s inaugural Chicago Street Race and the 2024 Democratic National Convention. Her efforts ensured strong community partnerships and tangible benefits for local neighborhoods.

“I’m honored to join the City of Joliet during such an exciting time,” said Sylvester. “With the upcoming Centennial of Route 66 and the transformation of Downtown’s City Square into a vibrant community hub, Joliet is poised for a cultural renaissance. I’m eager to collaborate with residents, organizations, and city leaders to create inclusive, memorable experiences that celebrate the city’s unique identity and energize its future.”

Sylvester holds a Master of Science in Integrated Marketing Communications from Northwestern University and a Bachelor of Science in Business from Miami University. She has also completed leadership coursework through the Urban Park Leadership Program at the City University of New York. Her past board involvement includes the Grant Park Music Festival and Chicago Children’s Theatre.

In her new role, Sylvester will oversee the planning and coordination of community celebrations, special events, and cultural initiatives—building on Joliet’s rich history while expanding opportunities for residents and visitors alike to connect, celebrate, and be inspired.

# # #

About the City of Joliet
The City of Joliet is located in Will and Kendall counties in the State of Illinois, 30 miles (48 km) southwest of Chicago. It is the county seat of Will County. At the 2020 census, the city was the third largest in Illinois, with a population of 150,362. For more information about the city, visit https://www.joliet.gov.

Media Contact: Rosemaria DiBenedetto, Media Engagement and Communications Director, Cell: 847-269-5556 or email: rdibenedetto@joliet.gov