elfreth's alley philadelphia

Find scenic streets and historic gems like Elfreth’s Alley in Philadelphia. (Photo: Getty Images)

Tips + Trends

A History Buff’s Ultimate Trip (by Train, Plane or Car) from Boston to D.C.

Major cities of the Northeast — and all the rich history they contain — are more connected than ever before. Choose between fast and reliable train service, a quick flight or a scenic drive, and get to exploring the artistic, political and historical landmarks of Boston, New York City, Philadelphia, Baltimore and Washington, D.C.

Here are a few ideas of what to see in each city.

As always, check for travel restrictions and closures before planning your trips.


History from the American Revolution to the tumultuous 1960s can be discovered in Boston. Start at the Paul Revere House, a Colonial home built in 1680 where the American Patriot lived. Then fast-forward several centuries to learn about the 35th president of the United States at the John F. Kennedy Presidential Library and Museum.

Art and architecture fans won’t want to miss the Isabella Stewart Gardner Museum, set in a building inspired by a Venetian palazzo. Once the elegant home of its namesake art collector, it is now a museum filled with paintings and sculptures.

For some fresh air, go for a stroll in the Arnold Arboretum, a 281-acre park designed by Frederick Law Olmsted that is home to a variety of rare plants. Afterward, check out Boston’s vibrant restaurant scene at Fox & the Knife, a rustic Italian restaurant known for excellent cocktails.

New York City

In addition to big-name sites like Ellis Island, New York City is also full of historical landmarks in its residential neighborhoods. Located in the heart of Harlem since 1914, the Apollo Theater has hosted musical legends from Billie Holiday to James Brown. Check out the weekly Wednesday Amateur Night to see up-and-coming talent.

Before hipsters moved to the Lower East Side, this neighborhood was home to immigrants from places such as Ireland, Germany and Eastern Europe. Explore The Tenement Museum through a variety of themed tours that bring the immigrant experience to life. On the Upper West Side, the New York Historical Society is a library and museum with themed exhibitions such as “Creating the American Republic.”

For a glimpse into Manhattan’s contemporary side, visit The Edge, the highest outdoor observation deck in the Western atmosphere (it has a glass floor 1,100 feet up).

Afterward, snack your way through Mercado Little Spain, an upscale food hall from Chef José Andrés.


Step back in time in Philadelphia with a stroll down Elfreth’s Alley, the nation’s oldest residential street. The pedestrianized alley, flanked by houses built between 1728 and 1836, is home to the Elfreth’s Alley Museum House.

Learn about the history of the U.S. Constitution at the National Constitution Center, an interactive museum with rare artifacts, hands-on exhibits and live performances. To experience an alternate side of American history, go inside the Eastern State Penitentiary, once the home of notorious criminals such as Al Capone.

Discover Philadelphia through the lens of Benjamin Franklin with the young Ben Franklin Tour. Starting at the Betsy Ross House, this is a walking tour with a twist: a guide who shares history through the art of rap.

When hunger strikes, settle in to Zahav, an Israeli restaurant known for hummus, mezze (small plates) and skewers grilled over charcoal.


After a stroll through the cobblestone streets of Fell’s Point, get to know some of Baltimore’s smaller historic attractions. Sports fans may want to see the Babe Ruth Birthplace Museum, while literature buffs might be drawn toward the Edgar Allan Poe House and Museum.

Climb aboard vintage streetcars at the Baltimore Streetcar Museum or visit The Star-Spangled Banner Flag House to hear stories about the women who sewed the American flag that inspired the U.S. National Anthem.

Entry to the Baltimore Museum of Art is free. Stop in to see a collection of 95,000 pieces of art, including the world’s largest holding of works by Henri Matisse.

To sip a cocktail in a historic environment, check out the Owl Bar inside the Belvedere, a hotel that dates back to 1903, and then get a taste of Maryland with a crab pot at Woodberry Kitchen.

Washington, D.C.

From the Arlington National Cemetery to the Lincoln Memorial, Washington, D.C., is full of important museums, monuments and government landmarks.

library of congress
The Library of Congress is a book lover’s dream. (Photo: Getty Images)

In addition to these icons, the city also contains smaller historic sites, including President Lincoln’s Cottage, once the private home of the 16th president and now a museum. To learn more about Civil Rights, visit the Mary McLeod Bethune House, a townhouse that was the first headquarters of the National Council of Negro Women.

History buffs may also be interested in the Library of Congress, the national library of the United States and home of the 19th-century Thomas Jefferson Building with rotating exhibitions.

Unwind at an underground beer garden with board games at Church Hall or eat vegetarian tacos at Chaia.