Hike like Teddy Roosevelt did at Sagamore Hill

“Over, under or through?”

Teddy Roosevelt re-enactor Joe Wiegand poses the question to a group of a half-dozen hikers on the trails of Sagamore Hill National Historic Site.

Looking out at a pool of ankle-deep water that has collected near the trail’s entrance to the beach, the hikers could be forgiven for hesitating to answer what was, after all, a rhetorical question. In fact, the real Teddy used to ask — or announce — this very same question to those accompanying him on his “Point to Point” hikes through the hills, swamps and woods of Sagamore Hill (then about twice the size of today’s 83-acre site in Oyster Bay).

This event, organized by the Friends of Sagamore Hill, is designed to mimic those treks that the 26th president, famous for his love of the outdoors, used to do on an almost daily basis. But does following in TR’s footsteps really mean having to slosh into freezing cold water? Wiegand, in a moment captured on video during the Dec. 6 hike, responds for the hikers.

“The answer is ‘through!’ ” he bellows, as he plunges ahead, arms swinging, while the other hikers come splashing behind.

“My shoes were totally soaked,” said Brian Tadler, laughing. Tadler is vice president and event organizer for the Friends group.

Wiegand — who has interpreted TR at the White House, on the History Channel and in many other venues — will be back at Sagamore Hill at some point in 2026, but the absence of a TR re-enactor needn’t deter hikers from enjoying a walk around one of Long Island's most important historic treasures.

At Sagamore Hill, the Roosevelt Home is open for tours on weekends, by advance reservation only. But the property is open to walkers seven days a week, from sunrise to sundown. Here, along a hilly, two-mile, partially paved loop of the perimeter of the park, one can enjoy nature, history and exercise.

“This was something [Roosevelt] did almost every day,” says Tadler. “Even when he had guests, he would take them out on hikes, sometimes whether they liked it or not.”

Your hike doesn’t need to be quite as strenuous as Teddy’s, which sometimes involved target shooting, rowing and riding a horse at various points along the way. You can enjoy the magnificent natural environment that is Sagamore Hill — and Long Island’s North Shore: The woodlands, open fields, beaches, and salt marshes here provide for enormous ecological diversity — including over 100 species of birds, and an abundance of animal life.

“For me it has always been an almost magical place,” says Stephen Gilroy, an East Norwich resident who has been regularly walking the grounds for years. He attributes his love of Sagamore Hill to “my devotion to American history, and the Roosevelts in particular — and equally so from the peace and quiet and natural beauty of the location.”

There’s also a sense of discovery and excitement — especially when the Rooseveltian spirit was invoked by Wiegand. On the Dec. 6 hike, participants explored the main trail, but also ventured into more obscure, colorfully named areas of the property, such as the Devil’s Punch Bowl and the Rifle Pit.

There are giggles as the group reaches the dry sands along Cold Spring Harbor, their hiking boots having been thoroughly doused going through the water.

“All right, count that the silliest thing we’ve done today,” cracks Wiegand, stepping out of character for just an instant, before bellowing TR’s trademark expression of approval at the satisfaction of a day outdoors at Sagamore Hill.

“Bully!”

For more information, visit friendsofsagamorehill.org.