SHORE PERSPECTIVES: Saltwater Cowboy Jack Brittingham Reins Supreme After 45 Years in the Saddle

By Kelley Gaskill

Jack Brittingham has ridden with the heart of Chincoteague- the Saltwater Cowboys- guiding wild ponies across Assateague channel for 45 years. His legacy is stitched into every hoofbeat and tide-washed memory of the annual Pony Swim, now in its 100th year.

Jack’s seasoned reins carry stories of saltwater and sentiment, rooted in a deep love for the island and its iconic ponies. Known for his steady hand and humble spirit, he embodies the rugged grace of this cherished tradition. With each ride, Jack reminds the community that heritage isn’t just remembered—it’s lived, year after year.

This week Kelley visited with Jack as he shared some fond memories from years past. As the oldest among the Saltwater Cowboys Jack has helped guide generations of wild Assateague ponies through the waters to Chincoteague, keeping alive one of the most beloved traditions of the Eastern Shore.