The Bridgeport Riding Club was organized in 1957. The founding members, Hollis Reynolds, JL Boswell, JR Johnson, Freeman Cash, Gordon Morris, Carl Cox, Cal Workman, Roy Pinion, Paul Brown, AB Bruster, and Glen Tackel, met at an all wood rodeo arena that was located where Harwood Park is now located. This is where the Wise County Youth fair was started and used for two years before it was moved to Decatur .
Hollis Reynolds was the first Bridgeport Riding Club president. The dues were $5 and members rode on Tuesday nights for years. Both old and young enjoyed riding & playing games on horseback. For a few months they stayed at the arena in the park, and then the Riding Club moved theTuesday night tradition to an arena owned by Jerry Buckingham about four miles north on Highway 101. The next year members rode a few months at an arena owned by Marvin Mercer located on Pleasant View Road . The next move was on Highway 920 about five miles from Bridgeport at a roping pen built by George Bean & Buddy Bean. The next year the Club was able to buy six acres where the arena is now.