In Wellington, the charities that share in a show-jumping fundraiser aiming to give away $2 million are not chosen by a committee. They are drawn from a drum. The Great Charity Challenge, now in its 18th year, closed its sign-up window on Oct. 15, and on Giving Tuesday, Dec. 1, every vetted Palm Beach County nonprofit gets a lottery ball and a random shot at a guaranteed $15,000 or more, with $100,000 for the charity paired with the winning team.

How the drawing works

Each qualifying charity is assigned a ball and placed in a raffle drum for a fully random draw, according to the Great Charity Challenge announcement on Wellington International's site. The drawing is livestreamed on the Great Charity Challenge's Facebook and Instagram on Dec. 1. Separate random draws among the vetted nonprofits also hand out smaller grants of $1,000 to $10,000.

The charities that are drawn are paired with competing teams at the event itself, on Saturday, Feb. 6, 2027, at Wellington International. Every participating charity is guaranteed at least $15,000. The one paired with the winning team takes the $100,000 grand prize.

From $500,000 to $26.8 million

The event was founded by a father and daughter, Mark and Paige Bellissimo. Its first year raised $500,000. It now gives away more than $1 million a year, and over 17 years it has distributed more than $26.8 million to 388 local charities, the organizers say. The 2027 goal is $2 million. Fidelity Investments is the sponsor.

Wellington International's preview of the 2027 Winter Equestrian Festival, published Oct. 2, puts last season's total at more than $2.3 million for more than 80 nonprofits, per the venue's season announcement.

Who was eligible

To be in the drum, a charity had to meet a short list of requirements:

  • Be a registered 501(c)(3).
  • Serve Palm Beach County residents and have a physical presence in the county.
  • Commit to spending at least 75 percent of the money it receives locally.
  • Have a non-discrimination statement or policy.

The window to apply opened Oct. 1 and closed at 5 p.m. on Oct. 15.

Masks on for 2027

Next year's theme is Once Upon a Masquerade: Tales from the Saddle. The organizers describe masked riders in storybook costumes and the venue styled as a moonlit masquerade ballroom.

How to follow along

  • The drawing: Tuesday, Dec. 1, 2026 (Giving Tuesday), live on the Great Charity Challenge's Facebook and Instagram.
  • The event: Saturday, Feb. 6, 2027, Wellington International, 3400 Equestrian Club Drive, Wellington.
  • More information: greatcharitychallenge.com.

Sources