With its storied heritage and presidential visits dating back to the Revolutionary War, Nassau County, Long Island, offers unparalleled opportunities to walk in the footsteps of some of America’s most influential leaders – and one of the county’s most famous residents, Teddy Roosevelt.
While President Roosevelt was undoubtedly one of Oyster Bay’s most esteemed residents, Nassau County’s presidential legacy extends far beyond his “summer White House,” Sagamore Hill. As you explore the county, you’ll see endless options to dive into some of history’s most meaningful moments, from routes once followed by George Washington’s clandestine spy ring to luxurious presidential retreats to celebrated spots where leaders drank, dined, entertained – and, no doubt, made decisions that shaped America yesterday, today, and tomorrow.
Here’s how to explore it all, whether you’ve got a weekend, a day, or even just an afternoon.
Sagamore Hill: A glimpse into Teddy Roosevelt's “Summer White House”
No presidential visit to Nassau County starts without a stop at Sagamore Hill, the beloved summer home of President Roosevelt from 1885 until his passing in 1919. Nestled in idyllic Oyster Bay, this National Historic Site offers a first-hand glimpse into the life of the 26th President of the United States in the place he loved most.
DID YOU KNOW?
President Roosevelt is the youngest U.S. president in history. He was 42 when he succeeded President William McKinley upon McKinley’s assassination.
While at Sagamore Hill, be sure to take the 45-minute guided tour that takes visitors both inside and around the property. The tour explores meticulously preserved rooms filled with President Roosevelt’s prized taxidermy and passes through lush gardens and original chicken coops. You’ll find evidence of his remarkable legacy as a conservationist and visionary leader everywhere you look.
Advance reservations are required to visit Sagamore Hill — you cannot purchase tickets onsite — and guided tours are offered Thursday through Sunday.
You can visit other locations on the grounds without a reservation. The Old Orchard Museum & Visitor Center is open Thursday through Sunday from 11:00am to 4:00pm. Visitors can also enjoy the picnic area and stroll various paths around the 83-acre property, including the nature trail, which leads to a beach in Cold Spring Harbor and a tidal salt marsh. Because President Roosevelt was a known animal lover, leashed dogs (AKA “Bark Rangers,” as they’re affectionately referred to) are welcome at Sagamore Hill.
As you’re leaving, pass by Youngs Memorial Cemetery, the home of the Roosevelt family gravesite and final resting place of President Roosevelt. It’s just minutes away, in the Village of Oyster Bay.
Raynham Hall Museum and the Culper Ring of Spies
Also in Oyster Bay, the Raynham Hall Museum invites visitors into the covert world of wartime espionage. Within the walls of this small museum, the fascinating story of the Culper Spy Ring unfolds.
During the Revolutionary War, seemingly ordinary citizens, including Nassau County resident Robert Townsend, played a pivotal role in shaping the course of history — very literally. Equally, or perhaps even better known as Samuel Culper, Jr., Townsend and numerous other spies transmitted secret messages to Colonel George Washington using special invisible ink and complex numeric codes.
Tours of the museum, which includes Townsend’s home, focus largely on the Culper Spy Ring, of course, but also highlight other aspects of local history. You’ll learn about colonial times and slavery in Nassau County and experience the tour with unique augmented reality tools.
Meals Fit for a President
Next up on your presidential exploration: the historic Milleridge Inn in Jericho. With origins dating back to 1672 — more than a century before the Revolutionary War began — this charming inn and restaurant (turned village) has welcomed many U.S. presidents over the years.
No presidential tour would be complete without booking brunch, lunch, or dinner at the Milleridge Inn. Not only will you have a chance to indulge in expertly prepared meals steeped in tradition, but you’ll also have a chance to wander through the inn and surrounding village. Stop into the Carriage House, one of the property’s first buildings, grab a treat from the bakery, and pick up a souvenir from the Christmas Store, which is open year-round.
Another must-try? During his first year as president, George Washington took a five-day tour of Long Island, stopping in Roslyn (then named Hempstead Harbor). While here, President Washington visited with Hendrick Onderdonk, a local landowner who built Long Island’s first-ever paper mill, at his own home. That house still stands today and has been transformed into a popular restaurant, Hendrick’s Tavern (for many years previously, it was called George Washington Manor).
From Kobe beef hot dogs and the lobster cobb salad to the classic Tavern Burger and show-stopping cocktails, everything on the menu is fit for a commander-in-chief. If you’re in town on a weekend, make early reservations. Hendrick’s has the best brunch in Nassau County. Don’t miss the homemade doughnuts!
Rounding out presidential-inspired dining options: Wild Honey Dining & Wine, just around the corner from the Raynham Hall Museum. Now a popular go-to, this space was once President Roosevelt’s former summer officer, minutes from Sagamore Hill. Today, Wild Honey’s serves up a creative and eclectic menu — think Pine Island oysters, fried calamari with pickled Asian vegetables, and grilled center-cut pork chops with caramelized peaches and sautéed kale for starters.
Live like a VIP (Very Important President) at the Garden City Hotel
Embodying classic luxe, it’s no surprise that the landmark Garden City Hotel has long been a haven for U.S. presidents. This iconic hotel’s unparalleled elegance and hospitality have attracted many distinguished guests, including Presidents John F. Kennedy, George Bush, and Bill Clinton.
Booking a stay here is the perfect way to cap off your presidential exploration of Long Island. Even if you’re a local, we highly recommend booking a room for a night or two and indulging in a memorable staycation. There’s tons to do around the hotel and onsite, including a spa, two bars, and Red Salt Room, led by celebrity chef David Burke. The latter is known for its epic Sunday brunch buffet as well as its signature candied bacon on a clothesline (yes, you read that right). From Theodore Roosevelt’s home at Sagamore Hill to the long-hidden secrets of the Culper Spy Ring, there are countless Nassau County destinations perfect for history buffs of all ages — and they’re just waiting to be discovered. All that’s left to do is book your visit and lean into the presidential lifestyle.
Want more ways to summer like a president? Share your pics with @VisitNassauCountyLI and be entered to win some Nassau County faves!
