Suffolk County officials have unveiled plans for an 80-mile trail linking Oyster Bay to Montauk, tracing the route of a horseback journey President Theodore Roosevelt made in 1903. The Theodore Roosevelt Historic Tourism Trail was announced in Sayville and is expected to be ready for hikers by early 2027.

The route follows a 30-mile ride Roosevelt made on July 23, 1903, from his Oyster Bay home to his cousin's estate in Sayville, and will wind through Nassau and eastern Suffolk with historical signage along the way.

A Local Stop In Sayville

Along the South Shore stretch, the trail passes Meadow Croft, an estate built around an 1867 farmhouse with an 1891 Colonial Revival addition. The Bayport-Blue Point Heritage Association discusses the property's history as one of several historic sites along the route.

Two Historic Anchors

The trail's western terminus is Sagamore Hill, Roosevelt's Oyster Bay home from 1885 until his death in 1919 and his "Summer White House" during his presidency. The eastern terminus in Montauk marks the site of Camp Wikoff, where the federal government quarantined more than 20,000 soldiers, including Roosevelt's Rough Riders, returning from the Spanish-American War in 1898.

The project is organized through a partnership of Suffolk County Parks, Discover Long Island, the Friends of Sagamore Hill, the Oyster Bay Historical Society and the Suffolk County 250 Planning Committee. The trail remains in the planning stages, and the county has not yet estimated construction costs. Read Full Story →