2019 Ocala Pumpkin Run (Florida)
Looks like it is still in the planning stages but another great multi day event is the Ocala Pumpkin Run. previous years have had it Fri-Sun in late October.
From last years WEB page:
Horsepower in Horse Country returns as Ocala becomes the backdrop once again for a premier car show and Fall Festival at the beautiful Castro Farms! Scheduled for the weekend of October 26-28th, 2018, car enthusiasts and spectators can look forward to three days of amazing car action and much more!
Our goal once again is to host an exceptional event where families can come together to enjoy cars of all makes and models from all eras, take a prized car to the corral for potential buyers to see, shop with some of the best automotive vendors, enjoy local merchants and their products and services, and then some more. Well have local bands, unique displays and demonstrations, and an incredible childrens area with FREE activities for them too!
Hopefully, I'll remember to come back here and update this when the official dates are out.