| Opened | September 23, 1940 |
| Last Race Date | September 20, 1998 |
| Racing Type | Thoroughbred |
| Abbreviation | Gbf |
| Purse Value Index | 3 |
| Signature Race | Unknown |
- 09/23/1940 First thoroughbred race run at Great Barrington Fair.
- 09/14/1968 A crowd of 27,048 set attendance record at Great Barrington.
- 09/18/1970 Mary Bacon becomes first female rider to win at Barrington Fair.
- 09/19/1971 Apprentice Ronald DeBoise collapses and dies after fourth race.
- 09/13/1975 Barrington Fair handles $987,306 to set all time record.
- 09/25/1983 This will be the last day of racing for eight years.
- 09/13/1991 Racing returns, but for only one season.
- 05/29/1995 A freak Memorial Day tornado rips through Great Barrington, track is heavily damaged.
- 09/04/1997 Racing returns for the final time in Great Barrington.
- 09/12/1997 Jockey Migual Figueroa dies from injuries from fall in fifth race.
- 09/20/1998 P.T. Pochahontas, last horse to have picture taken at Great Barrington Fair.