Big Brothers Big Sisters of Westchester & Putnam will host its annual Dream Big Gala at Westchester Country Club in Rye on October 23, with doors opening at 6 p.m. for a night built around one goal: finding mentors for the 120 children across Westchester and Putnam counties currently waiting to be matched. The evening will mix a cocktail reception, silent auction, dinner, live auction and entertainment, all aimed at raising money for one-to-one youth mentoring across the two counties.
A Night of Magic and Big-Ticket Auction Items
According to Yonkers Times, benefit auctioneer Jamie McDonald returns to host the evening, while Magic Mike Jacobson performs at the gala for the first time. Jacobson has appeared on America's Got Talent and The Ellen DeGeneres Show, and he holds the distinction of being the first magician named to Forbes' 30 Under 30 list as well as the youngest person ever admitted to Hollywood's Magic Castle.
Roughly 50 auction lots will go up for bidding, per the same report, ranging from house seats to the Broadway production of Other Desert Cities — starring Julia Louis-Dreyfus, Ed Harris, Allison Janney, Joe Keery and Lily Rabe — to five house seats to Aladdin with Emmy nominee Sherri Shepherd as the Genie. Other lots include Coach's Club seats at MetLife Stadium for a New York Giants game, a golf trip to Sea Island on the Georgia coast, a Tuscany vacation, and VIP tickets to Sting at the Paramount in Brooklyn. Additional items feature golf outings at Winged Foot or Whippoorwill, a portrait session with photographer Ben Larabee, tickets to women's soccer at the 2028 Los Angeles Games, and signed Giants memorabilia including a football signed by Arvell Reese and a Cam Skattebo jersey.
Gala Chair Reflects on the Stakes for Local Kids
Erin Mara Brooks, chair of the 2026 Dream Big Gala, said the event brings together an enjoyable evening with support for life-changing relationships for local children, the report notes. The organization will also recognize its 2026 Match of the Year, Big Brother Bob and Little Brother Rourke, who have been matched for four years. With Bob's guidance, Rourke organized a gift drive last year so other program children could receive presents at the chapter's holiday celebration.
Valerie Brown, interim chief executive officer of Big Brothers Big Sisters of Westchester & Putnam, said the organization recruits and trains mentors, carefully matches them with children, and provides continuing support, according to the same account. Westfair Communications previously reported that Ann Ellsworth, LCSW, was appointed chief executive officer of the chapter in September 2024, succeeding Valerie Brown, who had led the organization since 2015; the dossier does not clarify how Brown's current interim CEO role relates to that 2024 succession.
Why the Waitlist Keeps Growing
The need behind the gala is substantial. The chapter reports 120 children across Westchester and Putnam are waiting to be matched with a mentor, part of roughly 30,000 children on Big Brothers Big Sisters waiting lists nationally, per Yonkers Times. A separate count from River Journal found that, as of January 2026, Westchester County alone had 90 children on the waiting list, with local leadership pointing to an acute shortage of male mentors and male volunteers of color.
Those who do get matched can expect meaningful outcomes. River Journal reports that 100 percent of youth enrolled in the chapter advance to college, vocational training, or a paying job, with mentees also showing increased school attendance and improved problem-solving skills. A 2024 multi-method economic impact study examining three decades of Big Brothers Big Sisters data, evaluated using administrative records from the U.S. Department of the Treasury and Harvard University, found that mentees are 10 percentage points more likely to enroll in college by age 20 and go on to earn an estimated $56,000 more over their working lifetimes than non-participants, according to the Afterschool Alliance.
What It Takes to Become a Mentor
The commitment for adult volunteers, known as Bigs, is modest in scope but requires follow-through: four to six hours per month with an assigned Little across at least two monthly outings, for a minimum of one year, per River Journal's account of the chapter's volunteer guidelines. Screening includes background checks, interviews, and pre-match training before any pairing is made.
The chapter, founded in 1958, matches adult volunteers with young people ages 7 to 17 across Westchester and Putnam through both community-based and school-based mentoring programs, Yonkers Times reports. It became an independent 501(c)(3) nonprofit in January 2022 after 64 years as a sponsored program under Family Services of Westchester, a shift that Westfair Communications reported allowed the chapter to expand its fundraising and program scope across both counties.
Beyond the Gala: Year-Round Family Support
The chapter's work extends past matchmaking. For 15 years running, staff and volunteer Bigs have personally delivered Thanksgiving turkeys and food gift certificates to 91 program families in Yonkers, according to the Yonkers Times. A nationwide randomized controlled trial published in August 2025, which followed more than 1,300 youth across 17 affiliate agencies, found that youth assigned to a Big Brothers Big Sisters mentor maintained significantly lower rates of delinquency, substance use, and school absenteeism four years post-enrollment compared to waitlisted peers, per Arnold Ventures.
The gala's setting carries its own history. Westchester Country Club in Rye was established in 1922 as the Westchester Biltmore Country Club and features a historic main clubhouse designed by Warren and Wetmore alongside two 18-hole championship golf courses that hosted PGA Tour events, including the Westchester Classic, for four decades. The local fundraiser arrives as Big Brothers Big Sisters of America, which marked its 120th anniversary in late 2025, rolls out a national expansion initiative designed to extend mentorship access to 10 million young people through more than 230 affiliates operating in all 50 states, according to CBS Mornings.
Tickets and Sponsorship Levels
Individual gala tickets cost $350, while a Big Impact ticket runs $600 and covers both a guest seat and a program young person's attendance. Corporate and individual sponsorships range from $5,000 to $50,000, with a $10,000 sponsorship funding eight local children matched with a mentor for a full year and a $25,000 sponsorship funding twelve matches, per Yonkers Times. Tickets and sponsorships are available through the event's Qgiv page.
