My Five Favorite Historical Cities in the United States (a Historian’s Perspective)

The United States may not have the long recorded history as many other nations, but it still has remarkable places where one can explore its past. In every state, you can find unique historical sites brimming with local lore, but a few cities consistently draw me back as both a historian and a traveler. These are my five favorite historical cities in the U.S.—places where you feel history unfolding around you. While museums certainly play an important role, I’ve focused primarily on historic sites themselves, with a few exceptions where the buildings are historic in their own right.

Boston

Boston is a living textbook of the American Revolution, where centuries-old streets and buildings tell the story of the nation’s founding. Many of my favorite Boston historical sites are found on the Freedom Trail—a 2.5-mile walking path connecting 16 nationally significant sites tied to the American Revolution. Some of the places on the Freedom Trail that I visit over and again are:

• Old State House—the seat of colonial government where the Boston Massacre unfolded in 1770
• Old South Meeting House—meetinghouse best known as the gathering place for the Boston Tea Party
• Old North Church—famous for the “one if by land, two if by sea” signal that warned of British troops
• Paul Revere House—the preserved home of patriot Paul Revere and one of the oldest houses in Boston
• Massachusetts State House—a landmark government building crowned with a golden dome, still in use today
• Granary Burying Ground—final resting place of Revolutionary figures including Samuel Adams, John Hancock, and Paul Revere
• King’s Chapel Burying Ground—Boston’s oldest cemetery, reflecting early colonial burial traditions
• Faneuil Hall—a historic marketplace and meeting hall known as the “Cradle of Liberty.”
• Copp’s Hill Burying Ground—a hilltop cemetery offering insight into colonial Boston and views of the harbor
• Boston Common—America’s oldest public park and the starting point of the Freedom Trail
• The USS Constitution—also on the Freedom Trail, it is – the world’s oldest commissioned naval vessel still afloat, nicknamed “Old Ironsides.” Check out Bunker Hill while in Charlestown, which was a hub of Revolutionary action.
• North End of Boston—Boston’s oldest residential neighborhood is filled with colonial and immigrant history—and great Italian food, so make sure this is on your list
• Boston Harbor Wharves – Historic waterfront areas tied to trade, immigration, and the Boston Tea Party
• Beacon Hill – A preserved 19th-century neighborhood known for brick townhouses and cobbled, historic Acorn Street
• Fenway Park is a historic ball park (oldest active MLB stadium in the US); a trip through Boston’s history wouldn’t be complete without checking out the green monster.
• Isabella Stewart Gardner mansion—a Venetian-style palace built as the private home of an influential arts patron
• Boston Public Library—a grand Beaux-Arts building that was the first large free municipal library in the U.S.
• Trinity Church—a Romanesque Revival church that helped redefine American church architecture
• Salem (day trip)—a nearby historic city best known for its 1692 witch trials and maritime past
• Boston Viator link: https://www.viator.com/Boston/d678-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Chicago

Chicago tells the story of American ambition through groundbreaking architecture, urban innovation, and resilience after disaster—the Great Fire of 1871. Here are my favorite Chicago historical sites:

• Chicago Cultural Center aka People’s Palace—a former public library turned cultural hub, famous for its soaring spaces and stunning stained-glass domes
• Driehaus Museum—a lavish Gilded Age mansion that showcases Chicago’s late-19th-century wealth, design, and architecture
• Willis Tower aka Sears Tower—once the tallest building in the world, this skyscraper represents Chicago’s pioneering role in modern architecture
• 360 Chicago aka Hancock Tower—a mid-century modern skyscraper offering panoramic views and insight into Chicago’s vertical cityscape
• Chicago Architecture Tour—a guided look at landmark buildings that tell the story of Chicago’s rebirth and architectural innovation, like the Rookery, Carbide and Carbon Building, Chagall’s “Four Seasons,” Richard Daley Center with Picasso
• Federal Reserve Bank—a monumental Art Moderne building reflecting Chicago’s long-standing financial influence
• Wrigley Field—a beloved historic ballpark that has anchored Chicago sports culture since 1914
• Palmer House Hotel—one of America’s most storied hotels, long associated with politics, luxury, and innovation
• Buckingham Fountain—a grand Beaux-Arts fountain symbolizing civic pride and early 20th-century urban design
• Macy’s on State Street—a historic department store crowned by a magnificent Tiffany stained-glass dome
• Old Chicago Water Tower and Pumping Station—rare survivors of the Great Chicago Fire of 1871 and enduring city icons
• Chicago Viator link: https://www.viator.com/Chicago/d673-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

New York

New York City is a layered historical landscape where immigration, innovation, and cultural change shaped a global metropolis. Here are my favorite New York historical sites:

• Brooklyn Bridge—a 19th-century engineering marvel that helped unite Manhattan and Brooklyn
• Empire State Building—an Art Deco skyscraper that became a global symbol of American ambition
• Chrysler Building—a gleaming Art Deco tower celebrating industry, speed, and 1920s optimism
• Flat Iron Building—one of New York’s earliest skyscrapers, instantly recognizable for its triangular shape
• The Morgan Library—a historic private library turned public institution filled with rare manuscripts and art
• New York Public Library main branch—a Beaux-Arts landmark dedicated to free access to knowledge with a gorgeous reading room
• Rockefeller Center—a Depression-era complex blending commerce, art, and public space
• Ellis Island—the main immigration station for millions entering the United States between 1892 and 1954
• Statue of Liberty—an enduring symbol of freedom, democracy, and immigration
• Grand Central Station—a transportation hub and architectural masterpiece of the early 20th century
• 9/11 Memorial—a solemn site honoring the victims of the September 11 attacks
• Trinity Church and St. Paul’s Chapel—historic churches tied to colonial New York and the city’s resilience
• St. Patrick’s Cathedral—a Gothic Revival cathedral reflecting New York’s immigrant Catholic history
• Stonewall Inn—the birthplace of the modern LGBTQ+ rights movement
• Fraunces Tavern—a Revolutionary-era tavern associated with George Washington and early American politics
• African Burial Ground National Monument—a memorial honoring the burial ground of enslaved and free Africans in colonial New York
• MET Cloisters—technically a museum, but the buildings were built in 1938 making them a site to see in of themselves.
• New York Viator link: https://www.viator.com/New-York-City/d687-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Philadelphia

Philadelphia is the birthplace of American democracy, where the nation’s founding ideas were debated, written, and put into action. Here are my favorite Philadelphia historic sites:

• Declaration House—although permanently closed, you can still look at the outside of the house where Jefferson composed much of the Declaration of Independence
• Independence Hall Complex—the birthplace of American democracy, where the Declaration and Constitution were debated and adopted
• Athenaeum of Philadelphia—a historic library dedicated to architecture, design, and early American culture
• President’s House Site—the archaeological remains of the first executive mansion, revealing early presidential life and enslaved labor
• Liberty Bell Center—home to the iconic bell that became a symbol of independence and abolition
• Franklin Court—the site of Benjamin Franklin’s home and printing business, interpreted through modern exhibits
• Carpenter’s Hall—where the First Continental Congress met to coordinate resistance to British rule
• Christ Church—a colonial-era church attended by many Founding Fathers, including George Washington
• Elfreth’s Alley—the oldest continuously inhabited residential street in the United States
• Betsy Ross House—a traditional site linked to the making of the first American flag
• Arch Street Meeting House—a key Quaker site reflecting Philadelphia’s religious tolerance and reform movements
• Christ Church Burial Ground—final resting place of Benjamin Franklin and other Revolutionary leaders
• Free Quaker Meeting House—a rare surviving structure tied to Revolutionary-era Quakers who supported independence
• Reading Terminal Market—a historic public market reflecting Philadelphia’s immigrant and working-class food traditions
• Masonic Temple—an ornate 19th-century building filled with symbolism, ritual, and craftsmanship
• Philadelphia City Hall—a massive Second Empire–style building that once held the title of world’s tallest structure
• Eastern State Penitentiary—a revolutionary prison that transformed ideas about punishment and incarceration worldwide
• Philadelphia Viator link: https://www.viator.com/Philadelphia/d906-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Washington DC

Washington, DC is the symbolic heart of the nation, where monuments, memorials, and institutions reflect America’s ideals and struggles. Here are some of my favorite Washington, DC historical sites:

• Smithsonian Museums—historic structures that house the nation’s museums and research collections
• The White House—the official residence and workplace of the U.S. president since 1800
• US Capitol complex: the House and Senate Office buildings, the Supreme Court, and my favorite—the Library of Congress. It’s the heart of democratic debate.
• The Washington Mall with its memorials and monuments—some to note are the Lincoln Memorial, Thomas Jefferson Memorial, Martin Luther King Jr. Memorial, the WWI, WWII, Korean, and Vietnam War memorials, the Franklin Delano Roosevelt Memorial, and the Washington Monument.
• Arlington National Cemetery—a national military cemetery and place of remembrance
• Mount Vernon (day trip)—George Washington’s plantation home overlooking the Potomac River
• Frederick Douglass National Historic Site (day trip)—the preserved home of the abolitionist, author, and statesman.
• Washington, DC Viator link: https://www.viator.com/Washington-DC/d657-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Bonus sites

Of course, these five cities are only the beginning. America’s past stretches far beyond them—from St. Augustine and Colonial Williamsburg to Gettysburg, Seneca Falls, the Alamo, Pearl Harbor, and much more. Each tells an essential piece of the American story, and together they remind us just how rich and complex that story truly is.

Which historical city is your favorite? Let me know in the comments—and happy travels

Amy

Link to my Viator affiliate links for each city to make experiencing the past even more fun.

Boston Viator link: https://www.viator.com/Boston/d678-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Chicago Viator link: https://www.viator.com/Chicago/d673-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

New York Viator link: https://www.viator.com/New-York-City/d687-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Philadelphia Viator link: https://www.viator.com/Philadelphia/d906-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Washington, DC Viator link: https://www.viator.com/Washington-DC/d657-ttd?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Amy French, Ph.D., is the voice behind Roaming Historian. A professional historian and seasoned traveler, she shares stories that blend history and travel to give readers a deeper understanding of the places they explore.

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