| Date | Time | Main Event  | Event Name | Park Name | Cost |
| 12/05/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/06/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/07/08 | 2:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/12/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/13/08 | 2:00 PM | Dance | "Do-It-Yourself-Nutcracker" Ballet | Indian Boundary Park & Cultural Center | free |
| 12/13/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/14/08 | 2:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/19/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/20/08 | 7:00 PM | Theater | Shakespeare's "A Winter's Tale" | Chase Park | $8 ($5 = students, seniors, groups) |
| 12/05/08 | 3:30 PM | Gymnastics | Girl Gymnastics Demonstration | West Lawn Park | free |
| 12/05/08 | 6:00 PM | Tournaments | 2008 Holiday 10s tennis tourney | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/06/08 | 10:00 AM | Tournaments | 2008 Holiday 10s tennis tourney | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/07/08 | 10:00 AM | Tournaments | 2008 Holiday 10s tennis tourney | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/10/08 | 7:00 PM | Tournaments | Boxing Show | Brooks Park | $2 |
| 12/21/08 | 8:00 AM | Tournaments | Holiday Hockey Tournament | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/22/08 | 5:00 PM | Tournaments | Holiday Hockey Tournament | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/23/08 | 5:00 PM | Tournaments | Holiday Hockey Tournament | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/24/08 | 10:00 AM | Tournaments | Holiday Hockey Tournament Championship | McFetridge Sports Center (a.k.a. California Park) | free for spectators |
| 12/30/08 | 10:00 AM | Tournaments | Holiday Hoops: 3-on-3 Basketball Tournament | Brooks Park | free for spectators |
| 12/11/08 | 7:00 PM | Special Events | "The Four Quartets" by T.S. Elliot | Indian Boundary Park & Cultural Center | free |
| 12/18/08 | 6:00 PM | Special Events | Dia de Los Reyes: A Family Christmas Parranda | Humboldt Park | free |
| 02/07/09 | 6:00 PM | Special Events | Ballroom Dancing | South Shore Cultural Center | $5 |
| 02/15/09 | 4:00 PM | Special Events | Concert Series | South Shore Cultural Center | free |
| 02/16/09 | 10:00 AM | Special Events | Lyric Opera Special Performance | South Shore Cultural Center | free |
| 02/22/09 | 6:30 PM | Special Events | Concert Series | | free |