Long Island is getting an 80-mile trail stretching from Oyster Bay to Montauk that traces the historical footsteps, and hoofprints, of President Theodore Roosevelt. Local officials announced the Theodore Roosevelt Historic Tourism Trail in Sayville, unveiling plans for a route that will wind through Nassau County and eastern Suffolk, complete with signage sharing historical facts along the way.
Suffolk County officials expect the trail to be ready for hikers and history enthusiasts by early 2027, according to the New York Post. Suffolk County spokesman Michael Martino confirmed the early 2027 target during the announcement, per Newsday. County Executive Ed Romaine also participated in the announcement, according to the Post's reporting.
The route is inspired by an actual journey Roosevelt made. On July 23, 1903, the sitting president rode 30 miles on horseback from his Summer White House in Oyster Bay to his cousin John Ellis Roosevelt's estate in Sayville, drawing a crowd so large it alarmed his Secret Service detail, Newsday reports. Roosevelt was also described as an outdoorsman.
A Trail With Two Historic Anchors
The trail's western terminus sits at Sagamore Hill, the 23-room Queen Anne-style home Roosevelt built after purchasing 155 acres on Cove Neck in 1880 at age 22 for $30,000, according to the National Park Service. He completed the house in 1885, and it served as his primary residence until his death in 1919. During his presidency from 1901 to 1909, Sagamore Hill functioned as the Summer White House, where he hosted the envoys involved in the Treaty of Portsmouth before negotiations continued at the Portsmouth Navy Yard, according to the Oyster Bay Brewing Company — diplomacy that earned him the 1906 Nobel Peace Prize. The site was designated a National Historic Site in 1962.
Along the South Shore stretch, the route passes Meadow Croft in Sayville, an estate built around an 1867 farmhouse with an 1891 Colonial Revival addition. The Bayport-Blue Point Heritage Association discusses the property's history. The estate is among the historic properties along the route.
Montauk's Wartime Chapter
The trail's eastern terminus in Montauk carries its own weighty history. In August 1898, the federal government established Camp Wikoff there to quarantine more than 20,000 soldiers returning from the Spanish-American War, including Colonel Roosevelt and more than 1,000 Rough Riders battling tropical diseases like malaria, yellow fever, and typhoid, according to The East Hampton Star. The outlet notes that disease affected soldiers during the war. The Montauk Library provides additional historical context about the camp's construction.
Roosevelt's 1st U.S. Volunteer Cavalry, the famed Rough Riders who gained national attention after the Battle of San Juan Hill in Cuba, spent time at Camp Wikoff, per the Montauk Library. Earlier that same encampment, on September 6, 1898, Colonel Roosevelt visited the Montauk Point Lighthouse and signed the guestbook of lighthouse keeper Capt. J.G. Scott — a document The East Hampton Star notes is preserved today in the East Hampton Library's Long Island Collection.
Timing Tied to a Presidential Milestone
The trail's announcement landed on the 125th anniversary of Roosevelt's swearing-in as president. Roosevelt took office in 1901 at age 42 after serving as vice president under William McKinley, who was assassinated while in office; Roosevelt was later elected to a full term of his own. Born in Manhattan, he went on to live as an adult on Long Island and became known as a noted conservationist, a legacy the new trail's organizers are hoping to spotlight for a modern audience.
A Teddy Roosevelt impersonator who appeared at the announcement argued the trail offers something books can't. “People need to learn our history, to experience it, not just from books or in a college classroom,” he said, according to the Post. He added that a physical trail is more interesting because visitors can absorb more history simply by being there.
The project is being organized through a regional partnership involving Suffolk County Parks, Discover Long Island, the Friends of Sagamore Hill, the Oyster Bay Historical Society, and the Suffolk County 250 Planning Committee, according to a Friends of Sagamore Hill post, linking historic organizations across both Nassau and Suffolk counties. The trail remains in the planning stages, and the county has not yet estimated what it will cost to build.
