We went short notice last October when the weather report predicted warm and sunny weather. Did a sunset kayak tour and it was just magical. It was just us and the guide and the ponies.

I think I’m OP, and I just happened upon this thread again. Thanks for the tips!

OP has probably already gone, but if not - better chance of ponies close up is on the MD side of Assateague. On the VA side you can best see them by boat; views from the island itself are usually distant, although it's nice to bike around.

Anonymous wrote:It isn't the flies that will get you. It is the mosquitoes. I used a can of Deep Woods Off last time I visited over the summer, and I still had multiple bites on me. They are relentless and horribly unpleasant.
April or May would be best. Or any time after mid-October, just be aware that half of Chincoteague shuts down late fall through early spring.

+1 Came here to note the same.

I've camped in Assateague twice now and only go mid-October up to April. I camped on the bay side (which is were the bugs in warmer months are worst). Green heads and horseflies hurt when biting and they're on the beach side, but going during those months you'll avoid all that. Horses are everywhere on the Assateague side. You could stay in or just outside the park and drive through and see them non-stop. I visited the Chincoteague side once and will never go back. Took a boat tour (only way to see the ponies on that side) and it was right after they drove them across the water, separating the foals for people to buy. All the parent ponies were standing in a line staring at that side with their heads down. The boat driver said they do that every time after the foals are taken. Horrible. The Assateague side just gives them birth control for management, much more humane.

Anonymous wrote:It isn't the flies that will get you. It is the mosquitoes. I used a can of Deep Woods Off last time I visited over the summer, and I still had multiple bites on me. They are relentless and horribly unpleasant.
April or May would be best. Or any time after mid-October, just be aware that half of Chincoteague shuts down late fall through early spring.

I disagree, I think the biting black flies are the worst and seem completely unperturbed by Deep Woods Off and the like.

OP, if your camping/hiking/biking I would go in October. If your staying in Chincoteague and just want to see the ponies, you could go any time. Stay on the beach when you're not in your car and the wind will keep the flies away.