Before You Go to North Dakota: A Theodore Roosevelt Story Historians Rarely Tell

With the new Theodore Roosevelt Presidential Library opening in North Dakota, many travelers are taking a fresh look at one of America’s most fascinating presidents. The library in Medora will bring new attention to Theodore Roosevelt, the Badlands, conservation, leadership, and the rugged western landscape that helped shape his life.

For travelers searching for Theodore Roosevelt historic sites, Sagamore Hill in Oyster Bay and the Theodore Roosevelt Birthplace in New York City offer something a presidential library cannot always provide: the feeling of walking through the rooms where Roosevelt’s life actually happened.

I am glad to see that. Theodore Roosevelt belongs in North Dakota. The Badlands were an important part of his story and helped form his ideas about nature, strength, conservation, and character.  He is already honored in South Dakota on Mt. Rushmore. 

But before you go to North Dakota to learn about Theodore Roosevelt, there is another side of Teddy Roosevelt worth knowing.

It is not the side usually discussed by historians. It is not just about politics, the presidency, the Rough Riders, San Juan Hill, the Panama Canal, or national parks.

It is the side of Theodore Roosevelt experienced by a young boy walking through Roosevelt’s home in Oyster Bay, New York.

For me, the spirit of Theodore Roosevelt still lives most strongly at Sagamore Hill in Oyster Bay and at the Theodore Roosevelt Birthplace in New York City. One is where Roosevelt’s story began. The other is where he became most fully himself.

These are the Theodore Roosevelt homes that shaped my imagination as a child. They are also two of the best Theodore Roosevelt historic sites for travelers who want to understand the man behind the legend.

The Theodore Roosevelt Story That Began for Me at Sagamore Hill

I come from the same town where Theodore Roosevelt lived. As a boy, we visited Sagamore Hill on school trips.

At that age, I did not understand all the politics, reforms, treaties, conservation achievements, or presidential history. What I understood was adventure.

Imagine a little boy walking into Theodore Roosevelt’s home and seeing giant elephant tusks, bearskin rugs, mounted buffalo heads, a water buffalo head, Winchester rifles, swords from the Spanish-American War, stacks and stacks of books, and relics from a life that seemed almost too big to be real.

Nothing could inspire a child’s mind more.

To a young boy, Sagamore Hill was not just a historic home. It was a house of adventure. Every room seemed to say something about action, courage, curiosity, reading, travel, nature, and the wider world.

Roosevelt’s home made history feel alive.

After visiting Sagamore Hill, we would go home and play our own version of the charge up San Juan Hill. We were not thinking about military history in any sophisticated way. We were thinking about bravery, energy, adventure, and the larger-than-life spirit that Teddy Roosevelt seemed to represent.

Those childhood visits stayed with me.

Why Theodore Roosevelt’s New York Homes Still Matter

Most people associate Theodore Roosevelt with the Rough Riders, San Juan Hill, the Panama Canal, national parks, conservation, and the American West. Those are all important parts of his life.

But Theodore Roosevelt was also very much a New Yorker.

He was born in Manhattan. He made his family home on Long Island. He read, wrote, entertained guests, raised a family, worked, relaxed, and conducted presidential business from Sagamore Hill in Oyster Bay.

For travelers interested in Theodore Roosevelt, two New York sites belong at the top of the list:

Sagamore Hill National Historic Site in Oyster Bay, Long Island

Theodore Roosevelt Birthplace National Historic Site on East 20th Street in New York City

Together, these two Roosevelt homes tell a powerful story. The Theodore Roosevelt Birthplace shows where he began. Sagamore Hill shows where he lived, worked, thought, read, entertained, and became one of the most dynamic presidents in American history.

Sagamore Hill: Theodore Roosevelt’s Home in Oyster Bay

Sagamore Hill is located in Oyster Bay on Long Island. It was Theodore Roosevelt’s family home and the place where he lived from 1885 until his death in 1919. During his presidency, Sagamore Hill became known as the “Summer White House.”

But Sagamore Hill does not feel like a formal presidential museum. It feels like a home — a very unusual home, certainly, but still a home.

That is what makes it so powerful.

You see the rooms where Roosevelt read, wrote, entertained guests, worked, relaxed with his family, and surrounded himself with the things that mattered to him. Books are everywhere. So are reminders of hunting, nature, travel, politics, war, and family life.

The mounted heads, animal skins, weapons, trophies, and overflowing shelves of books tell you something about the man. Roosevelt was not one thing. He was a reader, writer, hunter, soldier, politician, conservationist, traveler, father, and president. Sagamore Hill brings all of that together in one unforgettable place.

It is not hard to imagine Roosevelt bursting into a room, speaking loudly, laughing, asking questions, telling stories, or preparing for the next great challenge.

For anyone planning to visit Theodore Roosevelt historic sites, Sagamore Hill is essential. It gives you a personal sense of the man in a way that few places can.

Visiting Sagamore Hill Again as an Adult

I visited Sagamore Hill again recently as an adult, and what struck me most was how different the world was when Theodore Roosevelt lived there.

No internet. No email. No cell phone. No instant communication. No 24-hour news cycle.

Today we think of presidents as being surrounded by constant communication. But Roosevelt lived in a time when even placing a telephone call could be an event.

One of the most remarkable stories connected to Sagamore Hill is that when Roosevelt needed to make a telephone call, he had to travel into the village of Oyster Bay, where the telephone was located at the local drugstore.

Imagine that today: the President of the United States, not reaching into his pocket, not stepping into a secure communications room, not sending a text or email, but traveling into town to place a call from the only telephone available.

It was a different time. A different pace. A different spirit.

And yet, something about that spirit still resonates.

Roosevelt’s world was slower in technology, but faster in action. He read deeply. He wrote constantly. He traveled widely. He fought. He explored. He spoke directly. He believed in physical effort, civic duty, and what he famously called the strenuous life.

That is what I still feel at Sagamore Hill.

Theodore Roosevelt Birthplace in New York City

The other essential Roosevelt home in New York is the Theodore Roosevelt Birthplace National Historic Site at 28 East 20th Street in Manhattan.

This is where Theodore Roosevelt’s story began.

It is easy to associate Roosevelt with the West, the Rough Riders, San Juan Hill, national parks, and the Badlands. But he was born in New York City. He began life as a sickly child in a Manhattan townhouse, and from that beginning he built himself into one of the most energetic figures in American history.

Theodore Roosevelt Birthplace is a wonderful place to visit because it shows the early Roosevelt — the child, the student, the collector, the reader, and the young man with curiosity and determination.

It also contains some remarkable Roosevelt relics and historical surprises.

My Favorite Panama Canal Trivia Question

One of my favorite trivia questions is this:

Where is the last shovelful of dirt taken out of the Panama Canal?

The answer surprises almost everyone: New York City, at the Theodore Roosevelt Birthplace on 20th Street.

I once took a tour of the Panama Canal. Our guide knew everything anyone could ever want to know about the canal — the engineering, the locks, the ships, the history, the construction, and the enormous challenge of building one of the world’s great waterways.

Then I asked him my favorite question:

“Where is the last shovelful of dirt taken out of the Panama Canal?”

He was stumped.

Absolutely stumped.

When I told him it was in New York City, at Theodore Roosevelt’s birthplace on 20th Street, he was amazed. In fact, he was so amazed that he told me his next vacation plans were going to be to New York.

That is the kind of surprising historical connection that makes the Theodore Roosevelt Birthplace so interesting. Roosevelt is often associated with the West, the Rough Riders, conservation, and the presidency. But in one New York City home, you find connections to his childhood, his family, Abraham Lincoln, the Panama Canal, and the larger story of America stepping onto the world stage.

Whether one is interested in Roosevelt as president, reformer, conservationist, explorer, soldier, or builder of the Panama Canal, the Birthplace connects those larger achievements to the boy who grew up in Manhattan.

Did Young Theodore Roosevelt See Abraham Lincoln’s Funeral Procession?

Another remarkable item associated with Theodore Roosevelt’s New York childhood is the famous photograph connected to Abraham Lincoln’s funeral procession in New York City.

Many historians and Roosevelt enthusiasts point to a photograph showing Lincoln’s funeral procession passing the Roosevelt family home. In an upstairs window are two children, identified by many as young Theodore Roosevelt and his brother Elliott.

Think about that for a moment.

A young Theodore Roosevelt may have looked out from a window in New York City and seen the funeral procession of Abraham Lincoln.

Decades later, Roosevelt himself would become President of the United States.

It is one of those moments where American history seems to fold in on itself — Lincoln, Roosevelt, New York, the Civil War, the presidency, and the future of the country all connected in a single image.

That is the kind of story that makes Theodore Roosevelt Birthplace worth visiting.

Sagamore Hill vs. Theodore Roosevelt Birthplace: Which Should You Visit?

If you have time, visit both.

Sagamore Hill in Oyster Bay is the better choice if you want to understand Roosevelt as an adult — the president, father, reader, hunter, conservationist, and public figure.

The Theodore Roosevelt Birthplace in New York City is the better choice if you want to understand where the Roosevelt story began.

Sagamore Hill feels personal, lived-in, and full of Roosevelt’s personality. The Birthplace gives context to his childhood, family background, New York roots, and early influences.

Together, they make a meaningful Theodore Roosevelt travel itinerary in New York.

Planning a Theodore Roosevelt Trip in New York

For travelers interested in Theodore Roosevelt, New York offers two excellent historic sites.

Sagamore Hill National Historic Site

Oyster Bay, Long Island
Best for understanding Roosevelt’s family life, presidency, personality, and “Summer White House” years.

Theodore Roosevelt Birthplace National Historic Site

28 East 20th Street, New York City
Best for understanding Roosevelt’s childhood, early influences, New York roots, and remarkable historical artifacts.

These two sites can be visited separately or combined into a broader New York history trip. One is in the heart of Manhattan. The other is in the quieter setting of Oyster Bay on Long Island. Each tells a different part of the Theodore Roosevelt story.

Why Visit Roosevelt’s Homes Before the New Library?

The new Theodore Roosevelt Presidential Library in North Dakota will surely be an important destination. It will help tell the story of Roosevelt’s connection to the Badlands, conservation, leadership, and the American West.

But Roosevelt’s New York homes tell another part of the story.

At Theodore Roosevelt Birthplace in New York City, we see where he began.

At Sagamore Hill in Oyster Bay, we see where he became most fully himself.

A presidential library can explain a life. A home can make you feel that life.

That is why Sagamore Hill and the Theodore Roosevelt Birthplace are so meaningful. These places are not just about exhibits. They are about atmosphere. They are about walking through rooms, noticing details, and feeling the presence of a man whose personality still seems to fill the space.

For me, Sagamore Hill will always be personal.

It is the place I visited as a schoolboy. It is where I first encountered the energy and adventure of Teddy Roosevelt. It is where elephant tusks, bearskin rugs, mounted buffalo heads, rifles, swords, and stacks of books made history come alive. It is where a boy could imagine charging up San Juan Hill and where an adult can still reflect on leadership, courage, family, curiosity, and public service.

Frequently Asked Questions About Theodore Roosevelt’s New York Homes

Where is Theodore Roosevelt’s home in New York?

Theodore Roosevelt’s most famous New York home is Sagamore Hill in Oyster Bay on Long Island. It was his family home and served as the “Summer White House” during his presidency.

Where was Theodore Roosevelt born?

Theodore Roosevelt was born in New York City. The Theodore Roosevelt Birthplace National Historic Site is located at 28 East 20th Street in Manhattan.

Is Sagamore Hill worth visiting?

Yes. Sagamore Hill is one of the best places to understand Theodore Roosevelt as a person. The home reflects his interests in reading, family, politics, travel, nature, hunting, history, and public service.

Can you visit Theodore Roosevelt’s birthplace in New York City?

Yes. Theodore Roosevelt Birthplace National Historic Site is in Manhattan and is operated by the National Park Service. It is one of the most interesting presidential historic sites in New York City.

What is the connection between Theodore Roosevelt and the Panama Canal?

Theodore Roosevelt strongly supported the construction of the Panama Canal during his presidency. One of the most surprising Roosevelt-related artifacts is the last shovelful of dirt taken from the Panama Canal, which is associated with the Theodore Roosevelt Birthplace in New York City.

What is the connection between Theodore Roosevelt and Abraham Lincoln’s funeral?

A famous photograph of Abraham Lincoln’s funeral procession in New York City shows two children watching from a second-story window. Many identify them as young Theodore Roosevelt and his brother Elliott.

What are the best Theodore Roosevelt sites to visit?

Some of the best Theodore Roosevelt sites include Sagamore Hill in Oyster Bay, the Theodore Roosevelt Birthplace in New York City, Theodore Roosevelt National Park in North Dakota, and the new Theodore Roosevelt Presidential Library in Medora, North Dakota.

Should I visit the Theodore Roosevelt Library or Sagamore Hill?

Ideally, visit both if you are interested in Theodore Roosevelt. The new Theodore Roosevelt Library in North Dakota will tell a broad story of Roosevelt’s life and legacy. Sagamore Hill in Oyster Bay gives visitors a more personal look at the home, family life, books, trophies, and rooms that shaped Roosevelt’s daily world.

Final Thoughts: The Roosevelt Spirit Still Lives in New York

I look forward to seeing the Theodore Roosevelt Presidential Library bring new attention to Roosevelt’s life and legacy. It is fitting that North Dakota will honor him in a major way, because the Badlands helped shape his character and his love of conservation.

But my fondest memories of Theodore Roosevelt are still in New York.

They are in the rooms of Sagamore Hill, where I first encountered the energy and adventure of Teddy Roosevelt as a child.

They are in the Theodore Roosevelt Birthplace on 20th Street, where the story of a sickly New York boy began before he became one of the most dynamic presidents in American history.

And they are in the lasting impression Roosevelt made on me: the sense that life should be lived with purpose, curiosity, courage, reading, action, and a little bit of adventure.

That is the spirit of Teddy Roosevelt.

And for me, that spirit still lives in Oyster Bay and New York City.