1

Start here, end there: Boston Common to Bunker Hill

Image: Roger Starnes Sr

There’s no official rule about where to begin, but most people kick things off at Boston Common. From there, the trail snakes through the heart of the city and ends at the Bunker Hill Monument in Charlestown. That final stretch leads to one of the most symbolic sites of the American Revolution. Of course, if you’d rather do it backwards, nobody’s stopping you—it’s your patriotic pilgrimage! Either way, the journey between these two iconic spots is packed with stories.

2

Where the trail begins: Boston Common’s surprising start

Image: Yassine Khalfalli

Boston Common might be a peaceful green escape today, but it began with a much more practical purpose. Established in 1634, it’s the oldest public park in the US, and it was originally used for grazing livestock, not lounging on park benches.

The land was purchased from Anglican minister William Blackstone and soon transformed into a communal area by the Puritans. Over time, it has witnessed protests, public speeches, and even British troops setting up camp.

3

Short and sweet: the 2.5-mile trail

Image: Naoki Suzuki

The Freedom Trail may only stretch 2.5 miles, but don’t let that fool you—it’s packed with history. The route winds through downtown Boston, passing 16 official landmarks. Most of the trail is flat and fully accessible, making it friendly for everyone. Just remember to bring comfy shoes!

4

Follow the red-brick road

Image: Yassine Khalfalli

No need for a map or GPS—just follow the red-brick line! That bright path under your feet is the Freedom Trail’s signature feature. It weaves its way from site to site, keeping you on track with zero guesswork.

The trail’s design was first suggested by a local journalist in the 1950s, who wanted to link all the key historical spots. It’s Boston’s version of a historical yellow brick road—minus the flying monkeys, of course!

5

Millions make the trip every year

Image: Aubrey Odom

More than 4 million people walk the Freedom Trail each year—and not just tourists. Locals, history lovers, and school groups all flock to this living museum. It’s one of the most popular attractions in Boston, and for good reason.

From Paul Revere’s House to the Boston Tea Party site, each stop tells a story. Even if you’ve walked it before, there’s always something new to notice. So go ahead—join the crowd.

6

No need to go in order

Image: Vika Chartier

Unlike history books, the Freedom Trail doesn’t follow a strict timeline. It’s organized by geography, not chronology, which means you can hop around without feeling lost. For instance, Boston’s North End has a cluster of must-see sites close together. It’s totally fine to explore them first and double back later. Just follow your curiosity—and your feet—along the red bricks.

7

Oldest this, oldest that, it’s a record-breaker

Image: Kelly Sikkema

The Freedom Trail is a goldmine of American "firsts." You’ll find the country’s oldest public park (Boston Common), its oldest public building (the Old State House), and even the site of the first major battle of the Revolutionary War (Bunker Hill Monument).

Paul Revere’s House is the oldest building still standing in Boston. And the Old North Church? That’s right—it’s the oldest church still standing in the country!

8

Rest in peace, revolutionaries

Image: Wenhao Ruan

Cemeteries might not sound exciting, but on the Freedom Trail, they can be. The Granary Burying Ground is the final resting place of Paul Revere and victims of the Boston Massacre.

Over at Copp’s Hill Burying Ground, you’ll find figures connected to the Salem Witch Trials and shipbuilders like Edmund Hartt. These aren’t just graves—they’re chapters in America’s story. And you’ll be walking right through them.

9

No replicas here

Image: Liubov Ilchuk

Every building and site along the Freedom Trail is the genuine article. Thanks to meticulous preservation, nothing is a recreation or reimagining—you’re standing where revolutionaries stood, seeing what they saw.

There’s something special about touching the same walls and walking the same halls. It’s as close to time travel as you’re going to get. How great is that?

10

Past meets present in every step

Image: Brett Wharton

Sure, you're here for the history, but Boston’s modern charm is hard to miss. Between historic stops, you'll find lively markets, cozy restaurants, and the buzz of city life all around. Grab a cannoli in the North End or sip coffee where patriots once plotted revolts. The Freedom Trail offers a perfect blend of old and new.

1

One World Trade Center

Image: David Vives

At a symbolic 1,776 feet, One World Trade Center proudly stands as America’s tallest building . Rising from the ashes of tragedy, this New York City landmark is a testament to resilience and unity.

Completed in 2014, it has been affectionately nicknamed the "Freedom Tower." Its sleek design features reflective glass that mirrors the sky, creating an ever-changing facade. The building houses offices, observation decks, and a museum dedicated to 9/11. Simply beautiful!

2

Central Park Tower

Image: Mason C

Central Park Tower, the world’s tallest residential building , reaches 1,550 feet into Manhattan’s skyline. Completed in 2020, it’s sometimes called the "Billionaires’ Row Tower" for its ultra-luxury apartments.

This architectural masterpiece offers jaw-dropping views of Central Park and beyond. It’s not just tall; it’s opulent, with a private club, pools, and even its own ballroom. If you’ve ever dreamed of living among the clouds, this is the place to do it (if you can afford it, of course).

3

Willis Tower

Image: Margo

Chicago’s Willis Tower, formerly known as the Sears Tower, was the world’s tallest building for 25 years (we did say there was some friendly competition going on!). Its 1,451-foot height dominates the skyline and has been a beacon of innovation since 1973.

The building’s unique design uses nine bundled tubes for extra stability against those famous Chicago winds. Visitors can step out onto The Ledge, a glass box extending from the 103rd floor, for a heart-pounding view. A true Midwestern marvel!

4

111 West 57th Street

Image: Parrish Freeman

Known as the "Steinway Tower," this ultra-skinny skyscraper is as much art as architecture. Rising 1,428 feet above Manhattan, it’s the thinnest skyscraper in the world and the fourth tallest in our country.

Its design nods to New York’s Jazz Age glamour, blending terracotta details with modern engineering. Completed in 2022, it houses luxury apartments that come with breathtaking views and equally jaw-dropping price tags.

5

One Vanderbilt

Image: Lukas Kyzur

Standing 1,401 feet tall, One Vanderbilt is a relatively new addition to New York City’s skyline. Completed in 2020, it’s located right next to Grand Central Terminal .

The building’s futuristic design is matched by its cutting-edge features, including Summit One Vanderbilt, an immersive observation experience. Its elevators take you to the top in a flash, and once you’re there, you’ll be treated to sweeping views of the city.

6

432 Park Avenue

Image: Miikka A.

At 1,396 feet, 432 Park Avenue is all about modern simplicity . Completed in 2015, it is one of the most recognizable buildings in the world.

ts grid-like windows give it a timeless look, but don’t be fooled—the apartments inside scream luxury. With amenities like private dining rooms and a spa, residents live the high life, pun intended! Love it or hate it, you can’t miss it.

7

Trump International Hotel and Tower

Image: Kenny Eliason

Chicago’s Trump Tower, standing 1,388 feet tall, is a gleaming addition to the city’s skyline . Completed in 2009, its reflective surface mirrors the surrounding beauty of the Chicago River.

This skyscraper combines luxury residences, a hotel, and fine dining. Its signature feature is the outdoor terrace, which offers stunning views of the Windy City.

8

30 Hudson Yards

Image: Frank Nürnberger

At 1,268 feet, 30 Hudson Yards is the centerpiece of New York’s futuristic Hudson Yards development.

Completed in 2019, it’s home to The Edge, the Western Hemisphere’s highest outdoor sky deck . The building boasts offices, dining, and even direct access to a luxury mall. Its sleek design symbolizes the city’s constant evolution. It has it all—just like the city itself!

9

Empire State Building

Image: Chris Barbalis

This may not be the tallest, but it certainly is one of the most iconic! The Empire State Building, at 1,250 feet, is a timeless symbol of New York City.

Completed in 1931 during the Great Depression , it was once the world’s tallest building. Its Art Deco design and iconic silhouette have graced countless movies and postcards. The city views it offers are simply unbeatable. No trip to New York is complete without a visit.

10

Bank of America Tower

Image: David Vives

Rising 1,200 feet in Midtown Manhattan, the Bank of America Tower is a green marvel. It was completed in 2010 and is one of the world’s most eco-friendly skyscrapers .

It uses innovative technology to reduce energy consumption and even collects rainwater. With its sharp, crystalline design, it looks as modern as its environmental features. This tower shows that sustainability and style can go hand in hand. Who knew going green could look so good?

11

St. Regis Chicago

Image: Andrew LaDeur

At 1,191 feet, the St. Regis Chicago adds a touch of elegance to the city’s skyline. Completed in 2020, its design is inspired by a flowing river , with undulating glass panels that shimmer in the sunlight. It’s a mix of hotel and residential spaces, with luxury oozing from every corner.

The building’s unique silhouette stands out in the architectural playground that is Chicago. If beauty were a competition, this skyscraper would be a top contender.

12

Aon Center

Image: Erol Ahmed

The Aon Center, at 1,136 feet, is a classic fixture in Chicago’s skyline. Built in 1973, it was originally clad in white marble, though granite replaced it later for durability. Its clean, rectangular design exudes timeless elegance.

Home to offices and observation areas , it’s a favorite among architecture lovers. You know how they are all about simplicity— the ultimate form of sophistication!

1

Point Roberts, WA: The 49th parallel accident

Imagine if you had to cross two borders just to get to the market for a gallon of milk. That’s actually a reality for residents of Point Roberts, Washington. That’s because, following the Anglo-American Convention of 1818, the 49th parallel divided Canada and the U.S. In 1846, the line was extended westward and then officially recognized by the International Boundary Commission in 1925.

However, a tiny tip of the Tsawwassen Peninsula poked out just below that line. Since then, the locals have lived in a boundary quirk. To get to the rest of Washington State by land, they must drive through Canada, show their passports, and do it all over again on the way back.

2

Statue of Liberty: Common misconception

If you want to start a friendly argument at a dinner party, ask whether the Statue of Liberty lives in New York or New Jersey. The funny thing is, both answers are technically right . While the statue physically sits in the waters of the Garden State, Liberty Island is legally an exclave of New York. This dates back to a 1664 land grant by the Duke of York in a document so vague and confusing that it took a 1834 Compact between the two states to settle the deal. New Jersey gets the water and the submerged lands, but New York keeps the monument.

However, the Federal Government actually manages the site through the National Park Service (NPS), providing security and maintenance.

3

The State of Franklin: Failed 14th state

If you think Tennessee was the 14th state to join the Union, there’s a catch. Before Tennessee, there was Franklin. In 1874, three counties in North Carolina felt neglected by their government and decided to strike out on their own . They even elected a governor, John Sevier, and printed their own money. They came just two votes short of being recognized by Congress as a formal state. Eventually, things got heated, and North Carolina sent troops, leading to a small civil war between the locals. By 1879, the dream of Franklin was dead and buried, and the territory became part of Tennessee.

4

Kentucky Bend

If you look closely at a map, there’s a piece of Kentucky that looks like it doesn’t belong. That’s the Kentucky Bend, also called the New Madrid Bend, a tiny peninsula in Fulton County that is almost completely separated from the rest of the Bluegrass State . The strange situation was the consequence of the massive series of earthquakes that took place in that area between 1811 and 1812, which were so violent they famously caused the Mississippi River to flow backwards for several hours. When the dust settled, the river had carved a new path that looped around this small patch of land, surrounded by Missouri and Tennessee instead of Kentucky. The 9 residents living there today go through Tennessee just to get to their home state.

5

The State of Deseret: The empire that almost was

Imagine a state so big it makes Texas look tiny. That almost happened back in 1894, when Mormon pioneers proposed the State of Deseret. The territory comprised what we now know as Utah, most of Nevada, parts of Arizona and Colorado, and a massive chunk of the California coast, including San Diego.

Had it been formalized, it would have been a powerhouse with its own seaport and total control over the West. However, Washington, D.C. wasn’t so keen on one group having that much territory and power, so they whittled it down, and we ended up having the states we know today.

6

The lawless "No Man's Land"

Have you ever wondered what happens when two governments simply give up on a piece of land? Between 1806 and 1821, there was a strip of land in what is now western Louisiana that was, literally, No Man’s Land. Neither the U.S. nor Spain, which owned part of the territory, could agree on the border, so they declared it "Neutral Ground" to avoid armed conflicts . The plan backfired as, with no laws to contain it, it quickly became a favorite for the outlaws in the West —meaning deserters and bandits hiding there were legally untouchable. The conflict was resolved by the 1819 Adams-Onis Treaty, which officially set the Sabine River as the legal boundary.

7

The Republic of the Indian Stream

In the early 1830s, people living in a small area between New Hampshire and Quebec were fed up, and in this case, taxes were the problem. Both Canada and the US were trying to collect taxes, and nobody likes being double-billed . In 1832, the residents essentially said "neither of them can tax us" and formed their own country called the Republic of the Indian Stream. They had their own constitution and Capitol for four years, until 1836, when the militia marched on the disputed territory to reclaim the land. It wasn’t until 1842, when the land dispute and the double-taxation was definitively resolved by the Webster–Ashburton Treaty, which assigned the land to New Hampshire.

8

The Northwest Angle: Mapping mistake of 1783

When the Treaty of Paris was signed in 1783 to end the Revolutionary War, the mapmakers used a chart that was flat-out wrong. They thought the Mississippi River started much further north than it actually did. Because of that mistake, a piece of Minnesota got cut off from the rest of the country . To this day, the "Northwest Angle" is the only place in the lower 48 states north of the 49th parallel. Much like Point Roberts, you have to cross a massive lake or drive through Canada just to visit it.

9

The District of Columbia’s "lost" corner

If you look at a map of D.C., you’ll notice it’s missing a chunk; it’s not a perfect square as it was originally intended. Originally, the capital was a perfect ten-mile square diamond , taking land from both Maryland and Virginia. But by 1846, things got tense. Residents in the Virginia portion, which included Alexandria and Arlington, were worried the federal government would abolish slavery in the District, which was the backbone of their economy. They successfully petitioned to have Virginia "take back" that portion of the land and subsequently changed the shape of the national capital forever.

10

UN Headquarters: International territory

If you want to feel international, go to the United Nations Headquarters on the East River in midtown Manhattan, New York. Once you cross that gate onto the 18-acre site, you are technically leaving the United States. You don’t need to show your passport, but that’s international territory, which means it has its own laws , its own security force, and even its own postal service. It is a legal hole in the middle of New York City.