Freedom Trail Pub Crawl | Boston, MA

Interested in experiencing the vivid history of Boston's Freedom Trail, but also keep it fun?  Head out on this walking tour of Bean Town with a pint or six along the way!

Interactive Google Map

I've created an interactive map that is available for public use on Google Maps.  Simply click this link and you'll be transported to this map.  Enjoy!

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Pre-Trail:  Charlestown

USS Constitution

If you're up for some extra walking you can start your day across the dirty water of the Charles River in Charlestown where you will begin with the USS Constitution. Often affectionately called "Old Ironsides," it is the oldest commissioned warship afloat in the world, having been launched in 1797. This iconic frigate played a significant role in the early years of the United States Navy, gaining fame during the War of 1812 for its resilient performance against British ships. Its sturdy oak hull, which earned it the nickname "Old Ironsides," helped it withstand enemy fire and remains a testament to early American shipbuilding prowess. Today, the USS Constitution is preserved as a historic vessel and museum ship in Boston, Massachusetts, where it continues to educate the public about early American naval history and maritime heritage.

Warren Tavern, Charlestown

While in Charlestown, be sure to start your crawlin' at the Warren Tavern.  This first pub stop is an historic landmark with a rich heritage dating back to 1780, making it one of the oldest continuously operating taverns in the United States. Located just steps from the Charlestown Navy Yard and the USS Constitution, the tavern has served as a gathering place for notable figures, including Revolutionary War heroes like George Washington and Paul Revere. Its colonial-era charm is reflected in the traditional wooden interiors and period decor, offering visitors a glimpse into 18th-century tavern life. Today, the Warren Tavern maintains its historical ambiance while providing a warm and inviting atmosphere, serving classic American fare and local specialties to both history enthusiasts and locals alike.

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Freedom Trail Pub Crawl

Copp's Hill Burying Ground

Copp's Hill Burying Ground, established in 1659, is one of Boston’s oldest and most historically significant cemeteries. Located in the North End neighborhood, it offers a glimpse into the city’s colonial past, with its grave markers telling stories of early settlers, influential figures, and victims of the American Revolution. Notable burials include several prominent figures such as Increase Mather, a key preacher and president of Harvard College, Edward Everett, a renowned orator and politician, and Edmund Hartt, the builder of the USS Constitution. The cemetery is also known for its distinctive graveyard architecture and panoramic views of the Charles River and downtown Boston from its elevated site. Today, Copp's Hill Burying Ground serves as a poignant historical site, preserving the legacy of Boston's early history amidst its modern surroundings.

Old North Church behind Paul Revere Statue

The Old North Church, officially known as Christ Church in the City of Boston, is an iconic and historically significant landmark located in Boston's North End. Completed in 1723, it is the oldest surviving church building in the city and is renowned for its role in American history. The church is famously associated with the American Revolution for its involvement in Paul Revere's midnight ride; on April 18, 1775, two lanterns were hung in its steeple to signal the approach of British troops by sea, a pivotal event in the lead-up to the battles of Lexington and Concord.  You may already be familiar with this tidbit from history due to the famous poem by Henry Wadsworth Longfellow, but it turns out the poem is filled with inaccuracies.  There is an interesting dissection of the poem on the NPS website.

Bova's Bakery

Next up is breakfast!  However, on the Google Map you will see the next link in the column as Regina Pizzeria.  This location is the original, and if it's lunch time when you get to this area... this is a great place to stop for lunch.  However, because it is the original location of this very famous Boston pizza parlor, there are often long lines... even to just grab a slice.  So, instead we recommend swinging by our favorite bakery, Bova's Bakery, to grab some savory and sweet treats to tide you over.  And don't worry, we WILL be getting a slice of Regina Pizzeria later on the tour, at another location.

FUN FACT:  Bova's Bakery was featured in the movie The Instigators starring Matt Damon and Casey Affleck.

Paul Revere House

​The Paul Revere House, located in Boston's North End, is an historic site of great significance because, you guessed it, it was the residence of the famed American patriot Paul Revere during the American Revolution. Built around 1680, this colonial-era home is the oldest surviving house in Boston and offers visitors a glimpse into 18th-century life. It was from this very house that Revere embarked on his legendary midnight ride on April 18, 1775, to alert colonial militia of the approaching British troops. Today, the house is a museum that preserves Revere's legacy and provides educational exhibits about his life, the Revolutionary War, and the history of the period. Its preservation and restoration allow visitors to experience the history and atmosphere of colonial Boston firsthand.

The Bell In Hand Tavern

It's time to belly up to the bar and grab yourself a pint!  Welcome to The Bell In Hand Tavern.  Established in 1795, it is an historic institution in Boston renowned for its rich heritage and enduring role in the city's social and political life. As Boston’s oldest continuously operating tavern, it has served as a vibrant gathering place for over two centuries, hosting a diverse clientele that ranges from early American revolutionaries to contemporary locals. Its name is derived from the bell that once hung outside, signaling the end of the workday and inviting patrons inside. Over the years, the tavern has witnessed significant historical events and conversations, contributing to its storied past. Today, if you're lucky, you'll even get a chance to meet Ben Franklin, as he wanders around Boston sharing his ideas with the locals and tourists alike.

The Green Dragon Tavern

Stumble across the alley and you'll find yourself at The Green Dragon Tavern.  Established in 1654, the Green Dragon is known as a key meeting place for the city's patriots during the American Revolution.  The tavern played a crucial role as a hub of revolutionary activity and discourse. It was here that influential figures such as Samuel Adams and Paul Revere gathered to strategize and discuss resistance against British rule, making it a focal point in the lead-up to the American Revolution. The tavern’s historic significance is highlighted by its association with the Boston Tea Party, where plans for the iconic protest were reportedly hatched. Today, the Green Dragon Tavern continues to honor its revolutionary past, serving as a symbol of Boston’s rich historical heritage and its role in shaping American independence.  While there try their Boston Tea Party cocktail - their house made sangria served in a tea pot for two!

Union Oyster House

One more pub before we stumble on, let's check out the Union Oyster House right next door!  Union Street was laid out in 1636, two years after the Boston Common was established, but there are no municipal records documenting the Oyster House's date of construction. All that is known is that the building has stood on Union Street as a major local landmark for more than 250 years. The first stirrings of the American Revolution reached the upper floor of the building in 1771, when printer Isaiah Thomas published his newspaper "The Massachusetts Spy," long known as the oldest newspaper in the United States. The restaurant was also a favored dining spot of President John F. Kennedy, who frequented it during his time as a Massachusetts senator. 

Faneuil Hall

It's time to get some carbs in our bellies, as we stroll through Faneuil Hall and Quincy Market to the take out spot for Regina Pizzeria!  Faneuil Hall, often referred to as "The Cradle of Liberty," is a pivotal historic landmark in Boston, renowned for its role in the American Revolution and its enduring legacy as a symbol of democratic ideals. Completed in 1743 and designed by architect John Smibert, the hall served as a marketplace and a forum for public discourse. It was here that prominent figures such as Samuel Adams and James Otis delivered stirring speeches against British policies, including the Stamp Act and the Townshend Acts, fueling revolutionary fervor. Over the years, Faneuil Hall has continued to function as a center for civic engagement and public gatherings, embodying the spirit of free speech and democracy. Its rich history and architectural significance make it a central feature of Boston’s Freedom Trail and a testament to the city’s influential role in American history.  You will find many, many food stalls inside Quincy Market - so if pizza isn't your preference, you will have no problems finding what is.

Site of the Boston Massacre

​The Boston Massacre, which occurred on March 5, 1770, was a pivotal event in American history that significantly escalated tensions between the American colonies and British authorities. On that fateful evening, a confrontation between British soldiers and a crowd of Boston colonists outside the Customs House led to the soldiers opening fire, resulting in the deaths of five colonists and injuring several others. The incident was fueled by longstanding grievances over British taxation and military presence in the colonies. The Boston Massacre became a powerful symbol of British oppression and was effectively used by colonial leaders like Samuel Adams and Paul Revere to galvanize public opinion against British rule. The event was later depicted in a famous engraving by Paul Revere and served as a catalyst for the growing revolutionary movement that eventually led to the American Revolution.

Old State House

The Old State House, completed in 1713, is a historic building in Boston that played a central role in the city’s early political and social life. As the seat of the Massachusetts colonial government, it was the site where key events leading up to the American Revolution unfolded. Notably, it was from the Old State House that British troops were ordered to fire upon the crowd during the Boston Massacre in 1770. The building also hosted the first public reading of the Declaration of Independence in Boston on July 18, 1776. Its Federalist-style architecture, characterized by its grand façade and ornate clock tower, has made it a prominent feature of Boston’s Freedom Trail. Today, the Old State House serves as a museum, preserving its historical significance and offering insights into the revolutionary era and the birth of American democracy.

The Old Corner Bookstore

The Old Corner Bookstore was originally constructed as an apothecary in 1718. The ground floor was later used as a bookstore that became the center of literary Boston and the meeting place of such notables as Emerson, Hawthorne, and Thoreau.  Unfortunately, it is no longer a bookstore.  As of 2024, there is a Chipotle in the location.

Old South Meeting House

​The Old South Meeting House, built in 1729, is an historic and influential site in Boston known for its pivotal role in the events leading up to the American Revolution. Originally established as a Puritan church, it became a central gathering place for Bostonians to discuss and debate political issues. It was within these walls that the Sons of Liberty, including prominent figures like Samuel Adams, organized resistance against British policies. The most famous event associated with the Old South Meeting House is the Boston Tea Party of 1773, where the decision was made to protest the Tea Act by dumping British tea into Boston Harbor. Today, the Old South Meeting House functions as a museum, offering visitors a deep dive into colonial life and the revolutionary spirit that shaped American history.

Boston Latin School

Founded in 1635, Boston Latin School is the oldest public school in the United States, reflecting Boston's long-standing commitment to education. Located in the heart of the city, the school has a distinguished history of academic excellence and has educated many prominent figures in American history, including four signers of the Declaration of Independence, such as Benjamin Franklin and John Hancock. The school's curriculum initially focused on classical education, emphasizing Latin and Greek, which was indicative of its rigorous academic standards. Today, Boston Latin School continues to uphold its legacy as a prestigious institution, known for its challenging curriculum and notable alumni, while embodying a tradition of academic rigor and public service that has spanned nearly four centuries.

King's Chapel

King's Chapel, established in 1688, is a historic Anglican church located in Boston and renowned for its distinctive architecture and rich heritage. Designed by architect Peter Harrison in the Georgian style, the church features a classic façade with a steeple and a unique interior that includes a series of memorials and a notable collection of colonial-era furnishings. King's Chapel was originally built as a chapel of the Church of England but has since evolved to serve as a Unitarian congregation. Today, King's Chapel stands as a vibrant symbol of Boston's religious and architectural history, offering services, tours, and cultural events while preserving its storied past.

Granary Burying Ground

The Granary Burying Ground, established in 1660, is one of Boston’s oldest and most historically significant cemeteries, situated in the heart of the city. It is renowned for being the final resting place of several notable figures from the American Revolutionary era, including Paul Revere, Samuel Adams, and John Hancock. The cemetery’s headstones, many of which date back to the 17th and 18th centuries, feature distinctive early American grave markers and epitaphs, reflecting the colonial-era traditions and artistry. The site is also notable for its role in the early history of Boston, serving as a burial ground for both prominent citizens and ordinary people.
The Granary Burying Ground is not only significant for its historical figures but also for its role in preserving Boston’s colonial heritage. The cemetery’s layout, with its narrow, winding paths and varied gravestones, offers a poignant glimpse into the past and a connection to the city's early history. Visitors can explore the well-preserved memorials and learn about the lives and legacies of those interred there, making it a key destination for anyone interested in American history. Be sure to look for the man with the binders at the entrance.  This guy creates these binders for visitors' use while exploring the burying ground.  It's got a great map and loads of information on all of the historical figures buried there.  Be sure to leave him a tip for his efforts on creating such a great guide!

Beantown Pub

It's time to take another break and wet our whistle!  Located across the street from the Granary Burying Ground is the Beantown Pub.  There is no real significance historically about the Beantown Pub, however it's conveniently located and has one of my absolute favorites on the menu - Boston Baked Beans served with Brown Bread.  So, there you have it.  Grab a beer, share some carbs, and take a break... we're almost done!

Boston Baked Beans and Brown Bread at Beantown Pub!

Bunnies on the State House lawn

The Massachusetts State House, completed in 1798 and located on Beacon Hill, is a pillar of Boston's political and architectural heritage. The cornerstone was laid by Samuel Adams, and the building stands on land bought from John Hancock. The red brick portion was designed by the legendary architect Charles Bulfinch. The building serves as the seat of the Massachusetts General Court, housing both the state Senate and House of Representatives. It is not only an architectural marvel with its neoclassical design and elegant interior but also a historic landmark where significant legislative and political decisions have shaped the state’s history. The State House is central to Boston’s Freedom Trail and offers guided tours that provide insights into its historical significance, the state’s governance, and its role in American history.

21st Amendment

The 21st Amendment Bar in Boston, established in 2002, holds a unique place in the city’s bar scene due to its tribute to the repeal of Prohibition in the United States. Named after the 21st Amendment, which repealed the 18th Amendment and ended the nationwide alcohol ban in 1933, the bar embodies a spirit of celebration and historical reflection. Situated in the historic South End neighborhood, the space was originally designed as a luxury hotel in 1899, with guests like Luisa May Alcott and Alexander Graham Bell, and was also known as the Bellevue Men's Club, and Golden Dome Club. 

Boston Common

Finally, take a stroll through the Boston Common. Set aside in 1634 as a military training field and grazing pasture, the Common is the oldest public park in America. The park served as quarters for British as well as Colonial troops, and later housed Civil War regiments. The British Army set out for the start of the Revolutionary War from what is now Park Square.

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Post-Trail:  Boston Tea Party

Abigail's Tea Room at the Boston Tea Party Ships & Museum

May we recommend a morning after stroll down to the Boston Tea Party Ships & Museum for a tea and scones breakfast at Abigail's Tea Room.  ​The Boston Tea Party, which took place on December 16, 1773, was a pivotal event in American history that significantly escalated tensions between the American colonies and British authorities. In protest against the Tea Act, which granted the British East India Company a monopoly on tea sales and allowed it to undercut colonial merchants, a group of colonists, disguised as Mohawk Indians, boarded three ships in Boston Harbor and threw 342 chests of British tea into the water. This bold act of defiance was intended to resist what the colonists saw as unjust taxation and infringement on their rights. The Boston Tea Party not only galvanized public sentiment against British rule but also set the stage for the Intolerable Acts, which further fueled the drive toward independence and ultimately led to the outbreak of the American Revolution.  Here at the museum you can visit replicas of the ships, learn more about the history, and have a cuppa tea.