The Chincoteague Drill Team was founded by Kendy Allen in 1996 and is the only one of its kind in the world. Kendy Allen got the idea for forming a drill team by seeing other drill teams perform at the Kentucky Horse Park. Since her Chincoteague Ponies were successful at different equestrian disciplines, she decided to form a drill team, adding this latest skill to the breed's list of accomplishments. Drill work is choreographed movements on horseback often set to music.

The team is made up of usually eight to ten riders, all who have had several years experience in riding and training Chincoteague Ponies. Kendy's own children have been members, and the other riders all hail from different areas of the East Coast. The ponies are Misty family members as well as ponies that were bought at the Pony Penning auctions or born off the island. During her lifetime Misty II was a member of the Drill Team and was the only one of Misty's grandfoals to be part of this new endeavor.

The Drill Team has made appearances at the Kentucky Horse Park, Equitana, the Washington D.C. National Horse Show, and the Pennsylvania National Horse Show. They regularly appear in parades on Chincoteague and other parts of the Eastern Shore. They have a standing invitation to perform at Kentucky Horse Park. The team has won several awards of their accomplishments, including being named the Youth Champion Drill Team at Equitana 2000. The Drill Team was also involved in donating a signed copy of Misty of Chincoteague to the island's library in 2003.

2006 saw the Drill Team's three consecutive wins in parade competitions as well as their very own book Black Mist and the Christmas Parade, written by Kendy Allen. They regularly participate in Christmas Parades on Chincoteague and at others on the Eastern Shore. For many years they performed smaller routines at the Chincoteague Pony Centre's nightly shows. Every year since 2006 the Drill Team performed before the start of the Pony Penning auction. The 2007, 2008, and 2009 Drill Team included Misty's Heaven's own Matt DesJardins usually aboard Misty's Heat Wave. The 2010 Drill Team traveled to Richmond, VA to march in the Virginia Gubernatorial Inaugural Parade. They were invited to perform at the 2010 World Equestrian Games at Kentucky Horse Park, but unfortunately the travel costs were too great. In 2018 three members of the drill team appeared live on the Today Show on NBC.

The Drill Team has performed for several years at The Dutta Corp Fair Hill International 3 Day Eventing Competition. They also perform at the Christmas tree lighting on Chincoteague. The Drill Team is headquartered at Kerkaken Acres in Bloxom, VA.