JWoW hosts two signature events each year.

* TEA-OFF TO GOOD HEALTH, a high tea and silent auction fundraiser, which is held in June.

* TEE-OFF FORE THE HEALTH OF IT, a golf tournament and business development symposium, which is held in the Fall of 2011.

Funds from both events are raised through ticket sales, sponsorships and generous donations. Since JWoW's inception in 2003, over US $300,000 has been donated to non profit community-based organizations in Jamaica and Washington, DC.