The year of 1650 marks the first land grant issued on Chincoteague Island, for 1,500 acres (6.1 km2).

In 1861, with the Civil War looming following the attack on Fort Sumter, the island voted 132–2 not to secede from the Union and against slavery.

The town saw minor action in the war via the Battle of Cockle Creek, which was fought in the bay in 1861.

The Assateague Lighthouse and Captain Timothy Hill House are listed on the National Register of Historic Places.

[13] Legend has it that the feral ponies on Assateague are descendants of survivors of a Spanish galleon that sank on its way to Spain during a storm in 1750 off the east coast, but the likelihood is that they are actually descended from domesticated stock, brought to the island by Eastern Shore farmers in the 17th century to avoid fencing requirements and taxation.

[14] In the Pony Penning, which has been held annually since 1925, horses swim across the shallow water between the islands.

All the horses are herded into large pens after running through the middle of town and down Main Street.

The town features numerous small hotels, bed and breakfasts, and campgrounds that serve visitors to the region, such as those patronizing the beaches.

With the designation of the nearby Wallops Flight Facility as the launch site for the Antares rocket and Cygnus cargo module used to resupply the International Space Station, there are large influxes of tourists whenever an Antares launch occurs.

The climate in this area is characterized by hot, humid summers and generally mild to cool winters.