Step back into the 18th century where revolution was often brewed in the bottom of a pewter mug. This self-guided walking route through historic Boston invites you to explore the legendary watering holes that served as the clandestine meeting spots for the Sons of Liberty. In Boston, history isn't just found in textbooks; it’s preserved in the dark wood booths and uneven floorboards of taverns that have stood for centuries. This neighborhood stroll takes you through the heart of Downtown and the North End, connecting the dots between the city's political awakening and its vibrant tavern culture. You will encounter landmarks like the Union Oyster House, America's oldest continuously operating restaurant, where figures like Daniel Webster once sat for a dozen oysters and a tall drink. This experience is more than just a nightlife crawl; it is a deep dive into the social fabric of colonial America. As you follow the path of this walking tour Boston, you'll see where the Boston Tea Party was likely planned and where patriots like Paul Revere shared news of British troop movements. The route also offers a poignant moment of reflection at the Granary Burying Ground, the final resting place of several Founding Fathers, before concluding at a pub named for the very law that ended Prohibition. Whether you are a history buff or a fan of atmospheric local favorites, this audio walk provides the flexibility to linger over a pint or move quickly between sites. Unlike a traditional guided tour Boston, you are in control of the pace, allowing you to soak in the architectural details and the spirited atmosphere of these iconic establishments without the pressure of a group schedule.

Numbers indicate the order of stops on the tour
Welcome to the Union Oyster House, a National Historic Landmark and the oldest continuously operating restaurant in America, serving patrons since 1826. Long before it was a restaurant, the building itself served as a dry goods store and even a temporary home for the exiled future King of France, Louis Philippe. As you look at the building's exterior, imagine the likes of Daniel Webster, the great orator, who was a daily regular here. He was known to consume at least six plates of oysters and a tumbler of brandy every single afternoon. The semi-circular oyster bar inside is original, and the 'Kennedy Booth' remains a tribute to JFK, who loved dining here in privacy. This is the perfect place to start your journey into Boston's storied past.
Just a short stroll away lies the Green Dragon Tavern, often called the 'Headquarters of the Revolution.' While the current building is a faithful reconstruction, the original site was where the Sons of Liberty—including Paul Revere and John Hancock—met in secret to plan the Boston Tea Party. British intelligence officers also frequented the area, making it a high-stakes environment for espionage. It was from this very location that Revere set off on his famous 'Midnight Ride' to Lexington in 1775. As you approach, notice the green dragon sign, a symbol that has beckoned weary travelers and revolutionaries alike for centuries. It remains a cornerstone of Boston's Irish-American pub culture.
Steps away is the Bell in Hand, which claims the title of the oldest tavern in the United States, established in 1795. It was founded by Jimmy Wilson, who had retired from his post as Boston’s last official town crier. Wilson was the man who walked the streets ringing a bell and shouting the news of the day—including the news of American independence. He famously refused to sell 'hard' liquor, focusing instead on high-quality ale, which was served in mugs that didn't have handles—you had to hold the bell-shaped glass itself. Today, it maintains that classic colonial vibe with thick wooden beams and a lively atmosphere that bridges the gap between the 18th century and modern Boston nightlife.
As we move toward the Common, we reach the Beantown Pub. While it may look like a standard Boston pub, it holds a unique geographical distinction. It is the only place in the world where you can drink a Samuel Adams beer while looking directly across the street at the grave of Samuel Adams himself. This cheeky bit of local trivia has made it a favorite for both locals and travelers. The pub itself is housed in a building with high ceilings and classic brickwork, offering a great vantage point of the historic Freedom Trail. It’s a perfect spot to reflect on the man who was both a master brewer and a pivotal figure in the American Revolution.
Directly across from the Beantown Pub is the Granary Burying Ground, established in 1660. While not a pub, this stop is essential to understanding the men who frequented the taverns you’ve just visited. This is the final resting place of three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine. You will also find the grave of Paul Revere and the victims of the Boston Massacre. The name 'Granary' comes from the public grain warehouse that once stood next door. Take a moment to walk the paths and look for the 'Soul Effigies'—the winged skulls carved into the headstones, a common Puritan symbol of the transition from life to death.
Our final stop is the 21st Amendment, located in the shadow of the Massachusetts State House. This pub is named after the amendment that repealed Prohibition in 1933, making it a fitting end to our historic pub route. The building originally served as a luxury hotel in the late 1800s and was once a favorite haunt of John F. Kennedy when he was a young congressman. Because of its proximity to the 'Hub of the Universe' (the State House), it is a legendary spot for political deal-making and 'lobbying' over a drink. It’s a cozy, subterranean space that captures the transition of Boston from a colonial port to a modern political powerhouse.
Download Zigway to experience "Colonial Pints: Historic Pubs of Old Boston" with AI-powered audio narration. Walk at your own pace while stories unfold around you.
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