Fall in Westchester isn’t only about apple orchards, foliage and weekends in Sleepy Hollow.
It’s also gala season.
From elegant waterfront cocktail receptions and black-tie dinners to live opera, dancing, auctions and evenings honoring some of the region’s most influential community leaders, September through November brings a packed calendar of charitable events to Westchester County.
And while these evenings offer plenty of reasons to get dressed up, they also raise money for causes ranging from children’s education and the arts to healthcare, parks, legal services and programs for people with disabilities.
If you’ve been looking for an occasion to pull out the cocktail dress or suit—and support a worthwhile cause while you’re at it—here are some of the standout galas and benefits happening around Westchester this fall.
Parks Are Essential Gala — New Rochelle
September 16, 2026 | 6 p.m.
Glen Island Harbour Club
One of the first major benefits of the season takes place in a beautiful waterfront setting.
The Westchester Parks Foundation’s annual Parks Are Essential Gala brings together community leaders, businesses, supporters and friends to celebrate the people helping preserve and improve Westchester County’s parks.
Funds raised during the evening support the foundation’s programs focused on preserving, enhancing and beautifying the county park system.
The setting adds considerably to the occasion. Glen Island Harbour Club sits on Glen Island in New Rochelle, surrounded by Long Island Sound, making it an especially picturesque location for an early-fall gala.
Westchester Parks Foundation Gala information and tickets
Equal Access to Justice Gala — New Rochelle
September 16, 2026 | 6–9 p.m.
Greentree Country Club
Legal Services of the Hudson Valley’s Equal Access to Justice Gala is expected to bring together nearly 300 people from Westchester’s legal, business, nonprofit and civic communities.
It’s the organization’s signature fundraising event, supporting free civil legal services for lower-income residents throughout the Hudson Valley.
The work supported by the gala includes preventing homelessness, assisting survivors of domestic violence, protecting the rights of people with disabilities and helping people who otherwise could not afford legal representation.
For those interested in Westchester’s philanthropic and professional communities, this is also one of the fall events likely to draw an interesting cross-section of local leaders.
YPIE Gala — Bronxville
September 17, 2026 | 6 p.m.
Barbara Walters Campus Center at Sarah Lawrence College
Yonkers Partners in Education will hold its 2026 Gala on the beautiful Sarah Lawrence College campus in Bronxville.
This year’s event honors Shari Turell and PwC and includes a cocktail reception by Zuppa Restaurant as well as a silent auction.
YPIE works with students to help prepare them for college success, making this one of the season’s notable education-focused benefits.
The Barbara Walters Campus Center also gives this gala an interesting setting—a contemporary gathering space within one of Westchester’s best-known college campuses.
Westchester Children’s Museum 10th Anniversary BIG Gala — Rye
September 26, 2026 | 6:30–11 p.m.
Westchester Children’s Museum at Rye Playland
This one sounds particularly fun.
The Westchester Children’s Museum is celebrating 10 years of play, discovery and learning with its 10th Anniversary BIG Gala.
The evening begins with Boardwalk Cocktails & Games and a silent auction, followed by dinner, a program and dancing.
Cocktail attire is requested.
And the setting makes this benefit different from a traditional ballroom gala: it’s happening right at the museum at Rye Playland.
There’s apparently plenty of enthusiasm for this one—the gala is already sold out, although the museum is accepting names for its waitlist as of September 12.
Taconic Opera’s “Opera Goes to Church” Gala — White Plains
September 24, 2026 | 7 p.m.
Caperberry Events @ CV Rich Mansion
For something a little different, Taconic Opera is combining a gala dinner with live opera.
Its 2026 theme is “Opera Goes to Church,” with professional singers performing selections inspired by dramatic church scenes in operas including Tosca, Il Trovatore, Manon, Suor Angelica and Don Carlo.
The evening will also honor longtime Taconic Opera supporters and performers Amy Rosato, Alan Briones and Hattie Herman.
Proceeds support Taconic Opera’s 2026–27 season.
Tickets are offered through partially tax-deductible donations at $150, $200 and $250 levels.
For classical-music lovers, this could be one of the most distinctive benefits of the fall.
Toasting to a Healthy Westchester — Tarrytown
September 30, 2026 | 5:30–8:30 p.m.
Abigail Kirsch at Tappan Hill Mansion
Healthcare meets philanthropy and business networking at the Westchester County Association’s Toasting to a Healthy Westchester.
The evening celebrates healthcare excellence and the people and organizations advancing healthcare throughout the region.
Guests will mingle with healthcare executives, business leaders, policymakers and community partners while enjoying cuisine and curated wines at Tappan Hill Mansion.
And it’s hard to imagine a more quintessential Westchester fall-gala setting.
The historic stone mansion sits on a hilltop in Tarrytown on what was once part of Mark Twain’s estate.
Tickets are currently $350 for WCA members and $390 for non-members.
October Galas
Groundwork Hudson Valley Annual Gala — Yonkers
October 8, 2026
This year’s Groundwork Hudson Valley gala comes with a theme that immediately makes it sound like a party:
Prohibition-era Yonkers.
Guests can expect live music, dancing and an auction while raising money for Groundwork Hudson Valley’s environmental and community programs.
The organization works on issues particularly relevant to urban areas of Westchester, including extreme heat, flooding, air pollution, access to green space, youth programming and environmental education.
For anyone who prefers a benefit with a strong theme rather than a traditional sit-down gala format, this one deserves a look.
Greater Mental Health of New York 80th Anniversary Gala
October 15, 2026
Greater Mental Health of New York is celebrating a major milestone this fall: 80 years of community-based mental healthcare.
And there are some particularly recognizable names among the 2026 honorees.
Dr. Tara Narula, cardiologist, ABC News chief medical correspondent and New York Times bestselling author, will be honored alongside Zac Clark, founder and CEO of Release Recovery and founding board member of the Release Recovery Foundation, and Dr. Philip J. Wilner, senior vice president and COO of NewYork-Presbyterian Westchester Behavioral Health.
Greater Mental Health serves approximately 15,000 people through behavioral-health services and community education in Westchester and Rockland counties.
This looks to be one of the season’s more prominent healthcare and philanthropic gatherings.
Cerebral Palsy of Westchester’s Hollywood Night — New Rochelle
October 22, 2026
Surf Club On The Sound
If there were ever a gala made for getting dressed up, this might be it.
Cerebral Palsy of Westchester is turning its annual Fall Gala and Pioneer Dinner Dance into Hollywood Night.
The organization is promising an evening of “glitz, glamour and generosity” at the waterfront Surf Club on the Sound.
Proceeds benefit CPW’s programs and services for people with disabilities, helping individuals live fuller and more independent lives.
Tickets are currently $200, with advance registration required.
Between the Hollywood theme and the Long Island Sound setting, this could easily be one of the most glamorous-looking benefits of the season.
CPW Hollywood Night Gala tickets
Maria Fareri Children’s Hospital Wines of the World
October 22, 2026
Another major benefit arrives on October 22 with Wines of the World, supporting Maria Fareri Children’s Hospital.
The event is part of WMCHealth’s fall fundraising calendar and offers a slightly different take on the traditional gala format, making wine and culinary experiences part of the evening.
This is one I’d keep an eye on as additional details about the 2026 event are released.
November Galas and Benefits
ArtsWestchester Benefit Featuring Black Violin — Purchase
November 7, 2026
The Performing Arts Center at Purchase College
This may be one of my favorites on the entire list because it combines a major benefit with an actual concert.
ArtsWestchester’s biggest celebration of the year will feature Grammy-nominated duo Black Violin, known for combining classical music with hip-hop.
The evening begins with a 5 p.m. VIP dinner and reception, followed by the Black Violin concert at 7:30 and a dessert after-party at 9:30.
The 2026 benefit honors M&T Bank, with proceeds supporting ArtsWestchester’s work to keep arts programming vibrant and accessible throughout the region.
This feels less like attending a fundraising dinner and more like having an entire night out built around the benefit.
ArtsWestchester 2026 Benefit and Black Violin concert
Saint Joseph’s Medical Center Annual Ball — Rye
November 7, 2026 | 6:30 p.m.
Westchester Country Club
For the traditional dinner-and-dancing gala experience, Saint Joseph’s Medical Center’s Annual Ball is one to put on the calendar.
Cocktails begin at 6:30 p.m., followed by dinner and dancing at 8.
This year’s honorees are Dr. Sandeep Gulati, Chief of Neurology, and hospital trustee Moira J. Kiernan.
The Westchester Country Club setting gives this one the feel of a classic formal fall benefit.
OCA-WHV Dynamic Achiever Awards Gala — New Rochelle
November 8, 2026 | 4–9 p.m.
Surf Club On The Sound
OCA-Westchester & Hudson Valley celebrates its 46th anniversary this year with its annual Dynamic Achiever Awards Gala.
The evening begins early enough for guests to enjoy sunset over Long Island Sound during cocktail hour before moving into the evening’s awards and celebration.
The waterfront setting alone makes this one worth noting for Westchester’s fall social calendar.
A Tree Grows in Pleasantville — White Plains
November 14, 2026 | 6 p.m.
The Opus Westchester
JCCA’s annual A Tree Grows in Pleasantville benefit moves into one of Westchester’s most sophisticated contemporary hotels for its 2026 celebration.
The November 14 event takes place at The Opus Westchester in White Plains, with “Casual Chic” listed as the attire.
For readers who like the charitable side of gala season but would rather skip a strict black-tie dress code, this may be particularly appealing.
Impact in Action — New Rochelle
November 19, 2026 | 5:15–8:30 p.m.
Glen Island Harbour Club
The Westchester County Association closes out its major fall event calendar with Impact in Action, its annual leadership event.
The evening recognizes some of the leaders, ideas and partnerships influencing economic development, public policy and innovation across Westchester.
It also promises to be a significant networking evening, bringing together influential figures from the county’s business and civic communities.
Tickets are currently $275 for members and $300 for non-members.
And once again, the waterfront setting at Glen Island gives the evening a particularly elegant backdrop.
Westchester’s Other Fall Season
When people think about fall in Westchester, the images are predictable.
Apple orchards. Pumpkin patches. Changing leaves. Sleepy Hollow. Weekends along the Hudson.
But there’s another side of the season that doesn’t receive nearly as much attention.
It’s the night when the cocktail dresses come out of the closet.
The tables at Westchester Country Club are set for dinner.
The lights come on inside a historic mansion.
Champagne is poured overlooking Long Island Sound.
An orchestra begins playing.
An auctioneer takes the stage.
And hundreds of people gather—not simply to enjoy a beautiful evening, but to raise money for organizations doing important work throughout the county.
That’s gala season in Westchester.
And from September through November 2026, there are plenty of reasons to get dressed up for a good cause.