| Tuesday | May 25 |
| 7:45 a.m. - 2:15 p.m. | Kohala HeliTrek Adventure – Exclusive
(NOTE: Advanced registration required. Call Hawaii Forest and Trail toll-free at 1-800-464-1993 to reserve your spot)
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| Wednesday | May 26 |
| 3:50 p.m. - 10:30 p.m. | Mauna Kea Summit & Stars Adventure – Exclusive (NOTE: Advanced registration required. Call Hawaii Forest and Trail toll-free at 1-800-464-1993 to reserve your spot)
|
| Thursday | May 27 |
| 8:30 a.m. - 7:00 p.m. | Hualalai Summit & Palani Ranch BBQ – Exclusive
(NOTE: Advanced registration required. Call Hawaii Forest and Trail toll-free at 1-800-464-1993 to reserve your spot) |
| 5:30 - 7:30 p.m. | Headmaster's welcome reception (pupus & drinks) for all alumni - Energy Lab, on campus |
| Friday | May 28 |
| Time to: | Picnic at the beach with classmates, tour campus, hike to the rain forest |
| Noon - 5:30 p.m. | Registration & Dormitory check-in - Alumni Office - Taylor Commons Bldg. |
| Evening | Reunion Classes - '55, '60, '65, '70, '75, '80, '85, '90, '95, '00 & '05 - parties at various on & off-campus sites TBA |
| 6:00 p.m. - Late | Waiki'i Clubhouse '85 Cluster Party (Busses to and from campus will be provided for a fee) |
| Saturday | May 29 |
| 9:00 a.m. - 5:00 p.m. | Registration & Dormitory check-in - Alumni Office - Taylor Commons BIdg. |
| 8:00 - 9:00 a.m. | Alumni Association Annual Meeting - Taylor Commons |
| 9:00 a.m. & 10:30 a.m. | Trail Rides - The Stables* |
| 9:00 - noon | Lauhala Weaving Class - Lower Lanai-Student Union HPA Bookstore OPEN for your shopping pleasure? |
| 10:00 a.m. | Campus Tour - meet at the Alumni Office |
| 10:00 a.m. - 5:00 p.m. | HPA's Isaacs Art Center Open - in town next to the Village Campus |
| 11:00 a.m. | Check-in at Hualalai Resort for 14th Annual Headmaster's Cup Golf Tournament - Advance registration only |
| 1:00 - 5:00 p.m. | Play Tennis - Rutgers Tennis Center Open" Go for a Swim - Dowsett Pool Open* Work-out - Nakamaru Fitness Center Open*
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| 3:00 -4:00 p.m. | Waterslide* |
| 6:00 - 7:00 p.m. | Social Hour - pupus & no-host bar - Taylor Commons |
| 7:00 - 8:00 p.m. | Traditional Hawaiian Luau - Taylor Commons |
| 8:00 - 9:00 p.m. | Headmaster's Welcome & Special Awards Group photos - Reunion Classes - Taylor Commons Lounge
|
| 9:00 - 11:00 p.m. | Music & Dancing |
| Sunday | May 30 |
| 8:00 -10:30 a.m. | Dormitory check-out - Dormitory Commons |
| 9:00 - 10:00 a.m. | Music and and alumni memorial reading - Davies Chapel |
| 11:00 a.m. - 12:00 p.m. | Personal Tour of Isaacs Art Center - meet at the Center |
| Time to: | Picnic at the beach with classmates, tour campus, hike to the rain forest |