My family went to the pony swim 6 yrs ago. It was so much fun , we had a great time!
We stayed at the Ramada in Salisbury Maryland, (which was about an hour drive) and I remember we had to get up at 4 am to drive to Chincoteague. The earlier , the better because there were a lot of people that attend the pony swim.
My Mother , sister, brother and niece chose to watch from the one side and my husband , daughter(5 at the time) and I decided to walk through the swamp (mud up to our knees) to see the ponies up close and personal. It is a long wait, we waited for at least 5 hours to see the ponies swim. They have to wait for low tide so that the young foals can make it across safely. It was hot and the bugs were bad , make sure you spray with bug spray. The mosquitoes were the worst. Use sunscreen, Take lots of drinks, and snacks because you have to wait so long. There were no bathrooms close to the area that we were at though.
Here is a good website Chincoteague Pony Swim
After they round up the ponies , they parade them through the town to a firemans festival , it poured rain the rest of the day so we didnt stay for much of the festival and didnt see the auction so I don't know about that.
I always enjoyed reading the books as a child and now my daughter likes to read the books too.
I def would make reservations for a hotel ASAP as they fill up fast around the this time of year.
Hope this helps you some : )