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 last week of September. - 6th Annual Tee-Off will be held in 2011.

Funds from both events are raised through ticket sales, sponsorships and generous donations. Since JWoW's inception in 2003, over US $200,000 has been donated to non profit community-based organizations in Jamaica and Washington, DC.