1. Robin Hood Foundation Gala

New York
Held annually in Manhattan, this soiree is the largest fund-raising event in the country, with proceeds supporting more than 200 community groups fighting poverty in New York City. Nearly 4,000 guests made their way to the Jacob K. Javits Center for the 2019 event, themed “Robin Hood to the Power of You.” The evening included performances from Sean Mendes and Pharrell, while Eli Manning, Kenan Thompson, and Gayle King also made appearances. Although the Robin Hood Foundation declined to release its fund-raising total, at least 23 people each pledged one million dollars throughout the course of the evening. Next: May 2020
See more: Do the Math: New York's Biggest Benefit Turned an Equation Into Event Design
Held annually in Manhattan, this soiree is the largest fund-raising event in the country, with proceeds supporting more than 200 community groups fighting poverty in New York City. Nearly 4,000 guests made their way to the Jacob K. Javits Center for the 2019 event, themed “Robin Hood to the Power of You.” The evening included performances from Sean Mendes and Pharrell, while Eli Manning, Kenan Thompson, and Gayle King also made appearances. Although the Robin Hood Foundation declined to release its fund-raising total, at least 23 people each pledged one million dollars throughout the course of the evening. Next: May 2020
See more: Do the Math: New York's Biggest Benefit Turned an Equation Into Event Design
Photo: Lisa Vecchione/BizBash
2. Naples Winter Wine Festival

Naples, Florida
This Florida-based festival raises money for the Naples Children and Education Foundation, which works to improve the lives of at-risk and underprivileged kids. Roughly 580 people attended the weekend-long event in 2019, generating $15.9 million; since it began in 2001, the festival has raised more than $191 million. In addition to daytime activities, guests attend intimate chef- and wine-driven dinners in private homes on Friday night and a lively meal and live luxury auction at the Ritz-Carlton Golf Resort in Naples on Saturday night. Auction items included high-end experiences like trips to France, Cuba, and Italy; a behind-the-scenes tour of the U.S. Supreme Court, along with a meet-and-greet with the justices; and tickets to the Tony Awards. Next: January 24-26, 2020
This Florida-based festival raises money for the Naples Children and Education Foundation, which works to improve the lives of at-risk and underprivileged kids. Roughly 580 people attended the weekend-long event in 2019, generating $15.9 million; since it began in 2001, the festival has raised more than $191 million. In addition to daytime activities, guests attend intimate chef- and wine-driven dinners in private homes on Friday night and a lively meal and live luxury auction at the Ritz-Carlton Golf Resort in Naples on Saturday night. Auction items included high-end experiences like trips to France, Cuba, and Italy; a behind-the-scenes tour of the U.S. Supreme Court, along with a meet-and-greet with the justices; and tickets to the Tony Awards. Next: January 24-26, 2020
Photo: Louis Venne
3. Two x Two for AIDS and Art Gala and Auction

Up from #5
Dallas
This annual gala and contemporary art auction benefits Amfar and the Dallas Museum of Art. Last year’s event at the Rachofsky House included performances from Alan Cumming and Diana Ross and raised $9.3 million, with $85 million generated over the past 30 years. New co-hosts Lisa and John Runyon are on tap to host in 2019, which will be sponsored by brands including Sotheby’s, Highland Park Village, Headington Companies, Neiman Marcus. Next: October 26, 2019
Dallas
This annual gala and contemporary art auction benefits Amfar and the Dallas Museum of Art. Last year’s event at the Rachofsky House included performances from Alan Cumming and Diana Ross and raised $9.3 million, with $85 million generated over the past 30 years. New co-hosts Lisa and John Runyon are on tap to host in 2019, which will be sponsored by brands including Sotheby’s, Highland Park Village, Headington Companies, Neiman Marcus. Next: October 26, 2019
Photo: Kevin Tachman
4. Museum of Modern Art's Party in the Garden

New York
MoMA’s annual Party in the Garden benefits the museum’s annual fund, educational programs, and the maintenance of the Abby Aldrich Rockefeller Sculpture Garden, where the fete is held. Six-hundred people gathered for the seated dinner this year, with the guest list opening up for 1,000 guests for the after-party. High-society attendees included Tory Burch, Jerry Speyer, and Glenn and Amanda Fuhrman. A fund-raising total was not made public. Next: Summer 2020
See more: See What You Missed From Spring Benefits Season
MoMA’s annual Party in the Garden benefits the museum’s annual fund, educational programs, and the maintenance of the Abby Aldrich Rockefeller Sculpture Garden, where the fete is held. Six-hundred people gathered for the seated dinner this year, with the guest list opening up for 1,000 guests for the after-party. High-society attendees included Tory Burch, Jerry Speyer, and Glenn and Amanda Fuhrman. A fund-raising total was not made public. Next: Summer 2020
See more: See What You Missed From Spring Benefits Season
Photo: Taylor McIntyre for BizBash
5. Crystal Charity Ball

Up from #6
Dallas
Each year, the Dallas social season ends with this black-tie gala, which was attended by more than 1,500 guests at the Hilton Anatole in 2018. Themed “A Celebration in Nouvelle-Orléans,” the decor recalled the French Quarter, the bar served up Hurricanes, and the menu featured bites like mini muffaletta lollipops and jumbo Gulf shrimp. The event capped off a year that saw the organization raise a record $6.5 million for children’s charities. Next: December 7, 2019
Dallas
Each year, the Dallas social season ends with this black-tie gala, which was attended by more than 1,500 guests at the Hilton Anatole in 2018. Themed “A Celebration in Nouvelle-Orléans,” the decor recalled the French Quarter, the bar served up Hurricanes, and the menu featured bites like mini muffaletta lollipops and jumbo Gulf shrimp. The event capped off a year that saw the organization raise a record $6.5 million for children’s charities. Next: December 7, 2019
6. Fight Night

Up from #7
Washington
Eighteen-hundred guests are scheduled to attend Fight for Children’s 30th annual fund-raiser at the Washington Hilton. The evening’s throwback theme will showcase three decades of an event that has generated nearly $70 million for underserved children in the Washington D.C. area. The organization has announced that 2019 will be the last iteration of Fight Night. Next: November 14, 2019
Washington
Eighteen-hundred guests are scheduled to attend Fight for Children’s 30th annual fund-raiser at the Washington Hilton. The evening’s throwback theme will showcase three decades of an event that has generated nearly $70 million for underserved children in the Washington D.C. area. The organization has announced that 2019 will be the last iteration of Fight Night. Next: November 14, 2019
Photo: Kevin A. Koski
7. Elton John AIDS Foundation Oscars Viewing and After-Party

Up from #8
Los Angeles
A-Listers show up every year for the Elton John AIDS Foundation Oscars Viewing and After-Party, held in a 40,000-square-foot tent in West Hollywood Park. In 2019, the event raised $6.3 million, taking the total up to more than $62 million raised since 1993. As many as 1,000 guests, including Paris Jackson, Kate Mara, and Diana Ross cycled through in the course of the party, which included a dinner, a live auction, and a performance by The Killers. Next: February 9, 2020
See more: Oscars 2019: Glamorous Party Highlights From the Week's Biggest Events
Los Angeles
A-Listers show up every year for the Elton John AIDS Foundation Oscars Viewing and After-Party, held in a 40,000-square-foot tent in West Hollywood Park. In 2019, the event raised $6.3 million, taking the total up to more than $62 million raised since 1993. As many as 1,000 guests, including Paris Jackson, Kate Mara, and Diana Ross cycled through in the course of the party, which included a dinner, a live auction, and a performance by The Killers. Next: February 9, 2020
See more: Oscars 2019: Glamorous Party Highlights From the Week's Biggest Events
Photo: Rich Fury/Getty Images for EJAF
8. After School Matters Gala

Up from #9
Chicago
At the 2019 edition of this annual gala, more than 150 Chicago teens who participated in After School Matters programs showcased their talents through hands-on exhibits, interactive displays, and unique performances. Nearly 1,000 guests made their way to Wintrust Arena for the event, which was presented by Blue Cross and Blue Shield of Illinois. A fund-raising total was not yet available. Next: September 2020
Chicago
At the 2019 edition of this annual gala, more than 150 Chicago teens who participated in After School Matters programs showcased their talents through hands-on exhibits, interactive displays, and unique performances. Nearly 1,000 guests made their way to Wintrust Arena for the event, which was presented by Blue Cross and Blue Shield of Illinois. A fund-raising total was not yet available. Next: September 2020
Photo: Courtesy of After School Matters