2. Tour Theodore Roosevelt’s Birthplace and Childhood Home

Take a free, intimate tour of Theodore Roosevelt’s childhood home, located on 28 East 20th Street in the Flatiron District. The recreated brownstone was rebuilt by the Women’s Roosevelt Memorial Association following the demolition of the original building in 1916. Today, it’s regarded as a National Historic Site, and holds artifacts from Roosevelt’s life, laid out across five period rooms. This includes the shirt he was wearing during an assassination attempt that took place as he was giving a speech in Milwaukee.

In addition to the tour, there are also gallery rooms and a political cartoon collection that is available to the public (fitting as Roosevelt was one of the most caricatured presidents of the United States). Make sure to also check out our previous article about other Roosevelt family houses you can find in New York City.