For January 2027, two organizer-confirmed dated events in this guide are the Hawaiʻi Mayor’s Cup senior softball tournament in Kona, January 18–22, and the Kamuela Philharmonic’s MasterWorks II concert in Waimea on January 24. If you hope to watch softball, confirm spectator access directly with the tournament organizer before making plans. Check an annual festival’s organizer before assigning it a January date.
January 18–22: Hawaiʻi Mayor’s Cup in Kona
The tournament organizer confirms January 18–22, 2027, for its senior softball event in the Kona area. It lists divisions on different days and says the Aloha/Mahalo party details are still to be announced. Players and families should use the tournament site for their division’s schedule and lodging information instead of assuming every team plays all five days.
Sunday, January 24: Kamuela Philharmonic in Waimea
Kamuela Philharmonic schedules “Tchaikovsky Discovers America!” for 2–4 p.m. Sunday, January 24, at Kahilu Theatre in Waimea. The program includes winners of its youth concerto competition. Check the orchestra’s current ticket page for seat availability before planning the drive.
A January 5–8 Waikoloa planning note
The Hawaii International Conference on System Sciences is scheduled January 5–8 at Hilton Waikoloa Village. It is an academic conference, not a visitor festival. If you are choosing a Waikoloa hotel for those dates, compare actual room availability before booking rather than assuming the conference affects every resort.
The Big Island Chocolate Festival says its 2027 dates are still to come. Do not assign it a January date on a travel calendar.
Plan by region
Kona and Waimea are separate destinations. If one event is your trip’s focus, choose an island base that makes its date easier, then build flexible days with our Hawaiʻi Island guide. Recheck the organizer page before travel for changes to schedules and venues.
