After travelling across 11 bridges to get from the mainland to the island, you'll find yourself amidst a quaint little village where time stands still, except for one week in July.
The pony swim is a large-scale event that takes place every July. The wild ponies are rounded up to make the swim from the Chincoteague National Wildlife Refuge on the Virginia side of Assateague Island to Chincoteage for the annual Pony Penning and Auction. The Virginia herd is owned by the Chincoteague Volunteer Fire Company. Although most of the locals leave town the week of the pony swim, it is definitely a sight worth seeing at least once.
Other times of year, the island is quiet and laid-back, a great place to get away from it all and just relax amidst the beauty that is Chincoteague.
The beach at the National Seashore is one of the prettiest on the Atlantic coast. The ocean waves are relatively mild, and lifeguards are on duty during the daylight hours. Farther up the beach, you can drive your 4WD right onto the beach and fish for flounder. If you visit the beach or the wildlife refuge in the late afternoon, you'll need insect repellent as well as sunscreen.
The long climb up the steep, winding stairs of the historic Assateague lighthouse is definitely worth the effort.
There are many places to stay, from the standard hotel room or a quaint B&B that serves afternoon tea to a luxury vacation home rental with its own dock and a hot tub.
There are several places rent canoes and jet skis for the hour, day, or week. The crabbing is spectacular, and many rentals come equipped with all the necessary gear.
Both the sunrises and sunsets are spectacular on the island. A great way to spend the evening is to sip on a frozen drink from the deck of one of the many restaurants facing Assateague Island and watch the sun go down on yet another perfect day.
Quick Tips:
In October, the annual oyster festival draws a huge crowd from around the country.
Many of the local restaurants and hotels have publications that include discount coupons for meals, miniature golf, and the island's ice-cream parlors.
http://www.chincoteague.com is a great source for events and lodging on Chincoteague Island.
Best Way To Get Around:
There is no public transportation. You can walk almost anywhere on the island, but you'll need a car or bicycle to get to the beach at the Chincoteague National Wildlife Refuge, which is a short drive across the bridge. Bicycles, including four-person, pedal-powered surreys, can be rented at various locations on the island.