The Best Boston Walking Tours,
4 Incredible Routes

Get The Most Out of Your Boston Walking Tours with CityDays

Discover more of Boston with CityDays!

Our Boston walking tours are designed to take you above and beyond your typical sightseeing experience. We’re dedicated to showing you the places you’d expect to see, but we slip in a bunch of cool hidden stuff along the way too. And the best part? You have to seek them out yourselves! 

By interacting with and learning about Boston’s streets, landmarks, history and famous figures, you’ll navigate your own way around Boston by answering puzzles, riddles and clues based on your surroundings. 

Our self-guided walking tours in Boston transform you into detectives, explorers and tour guides, giving you the freedom to discover the city your own way, in your own time, with people you know and love. 

From the moment you start until you finish the tour, you’re guaranteed to learn, have fun, make memories and get some fresh air and exercise. 

The Best Walking Tours in Boston

No lines, no waiting around, no hassle.

That’s part of what makes CityDays’ Boston walking tours the best in the city. 

We’ve created a model that allows you to take charge of your Boston walking tour. This ensures that you can walk at your own pace, take breaks whenever it’s convenient for you, and tour with whoever you want! Here’s how it works. 

Since we don’t physically attend your tour with you, you don’t even have to listen to our stories or facts (but you can - and should -  read all about them in your own time!). 

Remember though - just because we’re not there, it doesn’t mean we aren’t paying attention. We check our leaderboards and reward winners for having a great time on our Boston walking tours and we’re only a text away if you need additional help.

Boston History Walking Tours: Uncover Boston’s Inner Sanctum

From a 7th-century English priest who gave Boston its name to a rector-turned-songwriter who penned a famous Christmas carol, Boston has seen its fair share of history.

Our self-guided walking tours in Boston celebrate all the city’s cultural quirks and mysterious facts . 

In fact, we’re so fanatical about the Massachusetts capital that we’ve spent hours digging up cool quirks and interesting stories to share with you - here’s a sneak peek at what you can expect from our Boston walking tours (self-guided).

A Modern Aesop's Fable Exists in The City

Bostonians are probably familiar with the “The Tortoise and The Hare” sculpture in Copley Square, but you might not know that the sculpture - or rather the sculptor - indirectly led to the building of Boston’s skate park.

The sculptor’s name is Nancy Schön, and in 1995, she was distressed to learn that “The Tortoise and The Hare” sculpture was being used by bored / skate-happy teens as skate ramps. Schön visited the sculpture to talk to the kids who told her they had nowhere else to skate.

Emboldened, Schön spent 20 years campaigning for a skatepark for the city’s skaters to have somewhere to go. The park was supported by legendary skateboarder Tony Hawk, who donated 9 million dollars to the cause. In 2014, Schön’s wish was finally granted when the skatepark opened. The only trace of Schön you’ll find at the skatepark are some well-hidden engravings of a tortoise and a hare on the floor to commemorate her hard work.

Boston’s Chinatown Used to Be Called “Little Syria”

From the 1880s until the 1930s, Boston and Massachusetts was home to one of the largest Syrian and Lebanese diasporas in the U.S. 

The immigrants from Syria and Lebanon were primarily of Christian faith and it’s estimated that by the 1930s, there were 40,000 Syrians living in the state of Massachusetts.

Boston is Named After The Patron Saint of Boundaries, Trade and Travel

Most Bostonians know that the city’s name came from a town many miles away in England, but a few may not know that the other, less famous Boston was named after a Saxon Christian Saint by the name of Botolph.

Believed to have been born in the 7th century, Botolph was later venerated by the Catholic church as the Patron Saint of boundaries, trade and travel - a perfect candidate for Boston in Massachusetts where these three things played a pivotal role in the United States’ independence! 

Streets in The Back Bay Are Named Alphabetically

If you look up and see signs for Arlington, Berkeley and Clarendon Streets and wonder if you’re losing your mind, don’t worry - all’s well.

Back in the 1800s, when Boston was undergoing rapid growth and being laid out according to a grid pattern, the streets were named after English Earldoms (the titles of English Lords). 

The alphabetical names start from “Arlington” and stretch through to “Hereford”. 

Available Trails and Boston Walking Tours

Interested in finding out more about the kinds of self-guided walking tours in Boston we provide? Here’s where you get a tiny sneak peek into where you can find your next adventure…

Finding Freedom

Embark on “Finding Freedom”, a riddle-filled walking tour through Boston’s historic center that blends city exploration with the compelling story of America’s journey to freedom.

Trace clues around key landmarks and hidden treasures, delivering into their significant roles in the nation’s quest for liberty. Along the way, you’ll meet figures such as founding fathers, champions of equality, and an infamous British monarch. 

This interactive experience weaves entertaining puzzles through Boston’s streets with fascinating (and educational!) information, offering a dynamic way to learn about the city’s past and present.

Discover sites once steeped in unrest and revolution, as well as finding great spots for dining, shopping and more. Highlights include Faneuil Hall, Quincy Market, Old State House, Post Office Square and Old South Meeting House. 

The ideal debenture for families, friends or colleagues, Finding Freedom provides a comprehensive exploration of Boston’s rich history and vibrant culture.