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| 13-Apr-2008 - 22-Jun-2008 | Skokie, IL | Drive Charity Ride Series (# 7953) |
| 17-May-2008 | Mooseheart, IL | Mooseheart Bike Blessing and Run (# 7305) |
| 17-May-2008 | Caseyville, IL | Armed Forces Day Poker Run (# 7294) |
| 18-May-2008 | Oak Lawn, IL | Big Bikes Big Hearts Charity Motorcycle Run (# 6855) |
| 01-Jun-2008 | Sandwich, IL | Walneck Motorcycle Swap Meet and Show (# 6547) |
| 01-Jun-2008 | Antioch, IL | Wings Benefit Ride - 8th Annual (# 7371) |
| 05-Jun-2008 - 08-Jun-2008 | Effingham, IL | 2008 Illinois State H.O.G. Rally (# 5867) |
| 07-Jun-2008 | Yorkville, IL | Green Ribbon Motorcycle Ride and Rally (# 8246) - New |
| 08-Jun-2008 | Woodstock, IL | Ruben's Run (# 8176) |
| 21-Jun-2008 | Joliet, IL | Ilfreedomrun Supporting The Troops (# 7483) |
| 22-Jun-2008 | Grayslake, IL | Walneck Motorcycle Swap Meet and Show (# 6548) |
| 28-Jun-2008 | Effingham, IL | Legacy Harley Davidson Birthday Bash (# 8168) |
| 28-Jun-2008 | Joliet, IL | RFU's Memorial Run - 2nd Annual (# 6268) |
| 05-Jul-2008 | Shabbona, IL | Shabbona Hometown Festival Parade (# 8021) |
| 12-Jul-2008 | Savoy, IL | Marine Corps League Motorcycle Raffle And Toys For Tots Poker Run (# 7897) |
| 13-Jul-2008 | Villa Park, IL | MDA Ride For Life (# 7523) |
| 20-Jul-2008 | Elgin, IL | Chicagoland Ride for Kids (# 6824) |
| 24-Jul-2008 - 27-Jul-2008 | Lake Bluff, IL | Rogue Run - 2nd Annual (# 8173) |
| 27-Jul-2008 | Homer Glen, IL | S.O.B. Run - 5th Annual (# 7930) |
| 27-Jul-2008 | Yorkville, IL | American Legion Riders Post 489 Poker Run - 2nd Annual (# 7318) |
| 16-Aug-2008 | Shorewood, IL | Conrads Custom Bike Show (# 8240) - New |
| 17-Aug-2008 | Woodstock, IL | Walneck Motorcycle Swap Meet and Show (# 6550) |
| 24-Aug-2008 | St Charles, IL | Motorcycle Poker Run To Support Illinois Law Enforcement (# 7264) |
| 05-Oct-2008 | Sandwich, IL | Walneck Motorcycle Swap Meet and Show (# 6554) |