I am hoping to be able to attend this trip. I have been to Assateague many times and have kayaked the Assawoman Bay several times.
The many marked walks provide up-close looks at the nature and wildlife of the island. In the National Park (Maryland side), the ponies roam free and are "owned" by the national government.
I prefer this portion of the island in comparison to the Virginia/Chincoteague side where the ponies are owned by the Chincoteague Fire Company. This is where the pony swim takes place (usually July 4th). The 2 year-olds are sold off as a fundraiser for the Fire Company.

The $15 fee (per vehicle) that Jeff mentioned for the Maryland National Park goes to care for the ponies (medical, etc) and is good for 7 days. I purchase an annual pass every year.
You can get THIS close to the ponies but must remember that they are wild animals and should be treated as such! This was taken with my 18-55mm lens from the car window.
Like Jeff, I usually stay in the Fenwick Island area and drive the short distance to the Island. Tent and RV camping is also available on the island.
http://www.assateagueisland.com/assateague_camping.htmFor the day visitors, I recommend good walking or hiking shoes/boots, a hat, and bug repellent. I'm available for any questions.
