Chincoteague was a barrier island until the mid-1800s, when Assateague migrated so far south that it shielded Chincoteague from the ocean. The year of 1650 marks the first land grant issued on Chincoteague Island, for . Daniel Jenifer became the first English landowner. In 1671, settlers came to the island, and by 1672 there were large farms by Bishops, Bowdens, Jesters and Tarrs. By 1838, there were 36 houses on the island. 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 Native American name for the island is
Gingoteague, In 1962, a major
nor'easter winter storm, the
Ash Wednesday Storm, struck the coast. The town was completely underwater, and went for days without electricity. The storm destroyed almost all structures on Assateague Island, where development was just beginning. Following this, most of the island was preserved from development as
Assateague Island National Seashore in 1965. The
Assateague Lighthouse and
Captain Timothy Hill House are listed on the
National Register of Historic Places. In March 2020, the town received critical flood protection funding ($53.9 million).
Chincoteague ponies 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. In the
Pony Penning, which has been held annually since 1925, horses swim across the shallow water between the islands. At "slack tide" on the Wednesday before the last Thursday of every July, Chincoteague's "Saltwater Cowboys" herd the wild Chincoteague ponies from Assateague Island, across the Assateague Channel, to neighboring Chincoteague Island. If any animal is too small or weak to make the swim, it is placed on a barge and ferried over. All the horses are herded into large pens after running through the middle of town and down Main Street. Pony Penning takes place on the last consecutive Wednesday and Thursday in July. The actual swim occurs on Wednesday, the
Chincoteague Volunteer Fire Company auctions that year's foals on Thursday, and on Friday the remaining ponies swim back to Assateague. ==Tourism==