Crum was murdered in early April while eating lunch in his car.
The ride began in Williamson and went past the spot where Crum was killed, then out into Mingo County past his grave.
During his 93 days in office, Crum’s department managed more than 50 drug convictions.
Rosie Crum, Eugene ’s widow who was named sheriff after his murder, came to the Poker Run.
The ride was originally scheduled for early May as part of Rally in the Valley, but it was delayed because of rain.