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

122 S. Michigan Ave.

Image: Allen Boguslavsky

Why not start the trip at the place where it all began? For Route 66, the beginning is right in the heart of Chicago , at 122 S. Michigan Ave. Look for the iconic pylon near the intersection of South Michigan Avenue and East Adams Street.

Fun fact: the Mother Road didn’t always start there. Back in 1926, Jackson Boulevard at Michigan Avenue was the official launch point for travelers!

2

Gateway Arch

Image: Intricate Explorer

Follow your adventure in St. Louis with the Gateway Arch, a towering 630-foot tribute to westward expansion. This stainless-steel beauty isn’t just a landmark, it’s an experience in itself.

Ride the tram to the top for jaw-dropping views of the Mississippi River and the city skyline. It’s the perfect way to set the tone for the rest of your journey.

3

Route 66 Drive-In Theater

Image: Tim Mossholder

Ready for some vintage vibes? Swing by the Route 66 Drive-In Theater in Carthage, Missouri. This blast from the past offers double features under the stars , just like in the good old days.

Opened in 1949, closed in 1985, and re-opened in 1998, this drive-in theatre has functioned ever since and plays two movies from Friday to Sunday every single week. Bring your lawn chairs and a cooler, or cozy up in your car for the full retro experience.

4

The Golden Driller

Image: Jametlene Reskp

Now it’s time to meet the Golden Driller, a 76-foot-tall oil worker who’s been standing proud in Tulsa, Oklahoma, since the 1960s.

It’s one of the largest freestanding statues in the country and a nod to Oklahoma’s rich oil history. At the base, there’s a sign that reads: "The Golden Driller, a symbol of the International Petroleum Exposition. Dedicated to the men of the petroleum industry who, by their vision and daring, have created from God’s abundance a better life for mankind." Strike a pose with this gentle giant, and you’ll feel downright tiny.

5

Route 66 Museum

Image: Carol Highsmith's America

For the following stop, you can take a break to explore the Oklahoma Route 66 Museum in Clinton. In it, you’ll be able to see artifacts, photos, and exhibits celebrating the history of the Mother Road.

Wander through rooms themed by decade, and you’ll feel like you’re traveling through time. From the Dust Bowl to the heyday of diners, this museum paints quite a vivid picture of Route 66’s golden era. And, of course, you can go by the gift shop to get a road trip memento.

6

Cadillac Ranch

Image: Heidi Kaden

If you’ve ever wanted to graffiti a Cadillac, this is your chance. Cadillac Ranch in Amarillo, Texas, features 10 half-buried cars sticking nose-first out of the ground. It’s an open-air art installation that’s as weird as it is wonderful.

Grab a can of spray paint (provided by friendly locals or your fellow travelers) and leave your mark. Just be warned, it might only last a day before someone else paints over it!

7

Route 66 Halfway Point

Image: Vicky McLain

Welcome to Adrian, Texas, the official halfway point of Route 66! You’re 1,139 miles from both Chicago and Los Angeles, so take a breath and celebrate!

The MidPoint Café is famous for its "ugly crust" pies. Don’t trust the name; they are actually delicious! It’s a perfect pit stop to recharge and think about the fact that you’ve conquered half of the Mother Road. Only halfway to go!

8

Meteor Crater

Image: John Ballem - a collection of personal photos

Arizona is home to some magical attractions, and Meteor Crater is no exception. This massive impact site, located near Meteor City, was created by a meteorite over 50,000 years ago . Standing on the rim and peering into the 560-foot-deep crater, you’ll feel like a tiny speck in the universe. The visitor center has some cool exhibits on space and meteors, which is perfect for science lovers or anyone who likes their roadside stops with a side of awe.

9

Old Trails Bridge

Image: Jimmy Whitson

Crossing the Colorado River into Arizona, the Old Trails Bridge in Topock is a picturesque reminder of Route 66’s early days. Though it’s no longer open to traffic , it’s a popular photo spot for travelers.

The rusted steel beams and sweeping desert views will give you a beautiful moment. Pause here, take in the history, and imagine the countless cars that once went across its span.

10

Burger Hut

Image: Haseeb Jamil

Needless, California, may be small, but it’s big on charm, especially at Burger Hut. This unassuming little eatery is beloved for its old-school burgers, fries, and milkshakes. It’s the kind of place where the food is made with love , and the portions are hearty. Don’t take our word for it; just go try it!

After hours on the road, there’s nothing better than a juicy burger and a chance to stretch your legs. This spot is a gem along Route 66!

11

Hollywood sign

Image: Scott Greer

As you approach the end of Route 66, why not take a detour to see the world-famous Hollywood Sign? Perched on the hills overlooking Los Angeles, it’s a symbol of dreams and stardom .

Take a hike to the best viewpoints for some exercise (and epic photos, of course). Sure, it’s a bit off the beaten path, but what’s a road trip without a side quest?

12

Santa Monica Pier

Image: Joel Mott

You’ve made it! The Santa Monica Pier marks the official end of Route 66 . With its iconic Ferris wheel, arcade games, and ocean views, it’s the perfect spot to celebrate completing your journey.

Now you’re done, dip your toes in the Pacific, grab a cone of soft-serve, and reflect on all the memories you’ve made along the way. The Mother Road may end here, but the stories you’ve collected will last a lifetime.

1

J.R. Ewing (Dallas)

Image: Toglenn, CC BY-SA 3.0 <https://creativecommons.org/licenses/by-sa/3.0>, via Wikimedia Commons

If ambition had a face, it would probably be J.R. Ewing, the slick oil tycoon from the TV show Dallas . Manipulative, calculating, cold, incredibly greedy, and even treacherous, he checks all the boxes for one of TV’s most hated—and most memorable—villains.

2

Ross Geller (Friends)

Image: Philippe Berdalle, CC BY-SA 2.0 <https://creativecommons.org/licenses/by-sa/2.0>, via Wikimedia Commons

David Schwimmer brought to life one of the most memorable characters in American sitcoms. We’re talking about Ross Geller from Friends , a character who could easily land on both the "most beloved" and "most hated" lists. And that’s the charm of Ross: fans who adore him point to his generosity and intelligence, while those who can’t stand him blame his jealousy and tendency toward constant drama. Which side are you on?

3

Mr. Burns (The Simpsons)

Image: Erik Mclean

The millionaire Mr. Burns is the perfect example of a cartoon villain. And maybe it's not just his cold, calculating, and greedy nature that makes him so unlikable, but also his total inability to relate to or understand the problems of ordinary people. While it's hard to truly "hate" any character from The Simpsons , we can safely say he does not exactly inspire affection.

4

Kimmy Gibbler (Full House)

Image: Jason Leung

Kimmy Gibbler, played by Andrea Barber on Full House , is one of those characters who sparks mixed feelings. Some viewers find her loud, quirky, and intrusive behavior charming. However, for others, those same traits can be a bit too irritating. Whether you adore her or can’t stand her, no one could imagine the show without Kimmy.

5

Janice (Friends)

Image: Chester from Toronto, Canada, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

Those of us who watched Friends need just three words to remember this character: "Oh. My. God!" That’s Janice's trademark line, repeated almost every time she appears on the show. It’s not malice that gets under our skin, but her shrill voice, endless energy, and constant drama. And of course, she won’t leave Chandler alone, who does everything but be upfront about his feelings.

6

Livia Soprano (The Sopranos)

Image: HBO, CC BY 3.0 <https://creativecommons.org/licenses/by/3.0>, via Wikimedia Commons

Livia Soprano, mother of none other than Tony Soprano, manages to make us hate her from the very first season, and that’s part of what makes her such a compelling character. Bitter, cold, distrustful, manipulative, and calculating, Livia helps explain much of the protagonist’s behavior; through her, we glimpse the roots of Tony’s twisted mind.

7

Pete Campbell (Mad Men)

Image: Peabody Awards, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

Arrogant, manipulative, and always chasing status, these traits make Pete Campbell, played by Vincent Kartheiser, one of the least favorite characters on the iconic Mad Men . His hypocrisy and relentless ambition often lead him to overlook ethics and empathy, which is exactly why he earns a spot on this list.

8

Negan (The Walking Dead)

Image: Gage Skidmore from Peoria, AZ, United States of America, CC BY-SA 2.0 <https://creativecommons.org/licenses/by-sa/2.0>, via Wikimedia Commons

A villain so terrifying that he earns the hatred of viewers definitely deserves a spot on this list. We’re talking about Negan, the ruthless leader played by Jeffrey Dean Morgan on The Walking Dead . His brutality, arrogance, and need to control everything make him one of the show’s most frightening and unforgettable antagonists.

9

Nellie Bertram (The Office)

Image: Super Festivals, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

Played by the iconic Catherine Tate, Nellie Bertram joins The Office in the finale of the seventh season, and her excessive arrogance and pushy personality quickly make her one of the most irritating characters on the show. However, we have to admit it: on The Office , even the characters who get on our nerves often manage to make us laugh out loud.

10

Connor Roy (Succession)

Image: Super Festivals, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

A mix of wealth, eccentricity, vanity, greed, and a misplaced sense of power make Connor, the eldest Roy sibling in Succession , one of the least favorite characters in the series. His habit of taking advantage of others and expecting rewards he hasn’t earned is one of the key reasons he lands on this list.