Deep Hollow Ranch in Montauk, New York

Established in 1658, Deep Hollow Ranch is the oldest working cattle ranch in America. It originally served as a seasonal pasture for cattle and sheep who were driven to the tip of Long Island to graze on the maritime grasses each summer.

Over the centuries, ownership and use shifted. The ranch currently has approximately 40 horses and offers guided trail and pony rides to the public. Riders get the chance to saddle up, walk (or trot), and explore the historic trails which pass through over 1,100 acres of the dunes, meadows, and salty air of Montauk County Park.

Following the Spanish-American War, the large pastures served as a resting place for the horses and soldiers of Teddy Roosevelt's Rough Riders during their quarantine at nearby Camp Wikoff. The ranch features varied terrain, including ridges and hollows where deer and foxes roam, ponds where swans and geese gather, and sea- and driftwood-scented air where the occasional bald eagle flies.

Along the seaside trail, your horse may attempt to graze on the salt-tolerant grasses, scrub oak, and bayberries. Woodland paths descend to the shores of Oyster Pond, where Montauk's unique purple sand glistens in the sun as waves roll in. This distinctive color is created by ancient glacier deposits of garnet. The waves naturally sort the heavier crystals, leaving them in streaks along the shore that glow in the sun.

Rooted in nature and history, the ride provides a unique sense of transcendence that one can only experience at Deep Hollow Ranch.