May - June
| Thursday 5/28 | 7:00 PM | Rockleigh Criterium |
| Sat-Sun 5/30-5/31 | Various | Connecticut Stage Race |
| Saturday 5/30 | 5:45 AM | CRCA Scratch Race - 7 Laps Cats Paw |
| Thursday 6/4 | 7:00 PM | Rockleigh Criterium |
| Saturday 6/06 | 9:30 AM | BALLOON FESTIVAL CLASSIC ¾ Race |
| Sunday 6/07 | Various | Bear Mountain Seven Lakes Time Trial ITT&TTT) |
| Afternoon | Tour of High Bridge | |
| Thursday 6/11 | 7:00 PM | Rockleigh Criterium |
| Saturday 6/13 | 5:45 AM | CRCA Power Points Race - 7 Laps Met |
| 5:45 AM | Tour of New York - Prospect Park | |
| Sunday 6/14 | 8:45 AM | 2009 Criterium New York - FBF |
| Thursday 6/18 | 7:00 PM | Rockleigh Criterium | Fri-Sun 6/19-6/21 | Giro Di Jersey - 3 Day Points Omnium |
| Satuday 6/20 | 5:45 AM | CRCA Scratch Race - 7 Laps Cats Paw |
| Sunday 6/21 | 9:15 AM | Housatonic Hills Road Race (Pre-Reg Only) CLOSED |
| ? | Skyscraper Harlem Cycling Classsic | |
| Thursday 6/25 | 7:00 PM | Rockleigh Criterium | Saturday 6/27 | 5:45 | CRCA Scratch Race - 7 Laps Met |
| Sunday 6/28 | 6:32 | Cadence Cup Prospect Park Series |
| Thursday 7/02 | 7:00 PM | Rockleigh Criterium |
| Thur-Sun 7/02-7/05 | Various | 50th Annual Fitchburg Longsjo Classic Stage Race |