It actually depends on your taste in automobiles
The two most popular are in September. The Shades of the Past is the oldest.
It was originally a pre 49 vechicle event BUT now allows up to 1972 vechicles
It is the event I always go to.
The other event is the Grand Run. Fashsioned after the Shades of the Past but has no year restrictions that I am aware of.
The SHADES OF THE PAST
event has way more resistered vehicles than the The Grand Run ... but the town is full of cars both weekends. The Shades event ... has more of the 30's, 40's amd 50' where the Grand Run is more Camaro, Mustang and Chevelle type vehicles.
I have been to both in the same year ( they are 1 week apart ). But for the past 4 or 5 years ... I just go the the Shades.
I have been to all 30 of the Shades events ... because I have 32 Fords. SO ... I may be biased.