Boston’s Freedom Trail is filled with stories of revolution, rebellion, and the people who shaped American history—but some of the city’s best stories can also be found on your plate!
On this 3-hour food and history adventure, follow your local guide through Downtown Boston and along the Freedom Trail through the foods, businesses, and unexpected stories that shaped the city. Along the way, enjoy generous tastings of iconic Boston dishes while discovering why they became part of Boston’s culinary identity.
Your journey begins at one of Boston’s historic pubs with a hearty, slow-cooked traditional dish rooted in colonial New England. Learn how this slow-cooked dish traces its roots to Native American traditions, why Puritans embraced it, and how molasses helped give Boston its famous “Beantown” nickname. Then, uncover the darker side of molasses as you hear the unbelievable story of the Great Molasses Flood.
Continue along the Freedom Trail and pass by the Granary Burying Ground, the final resting place of figures including Paul Revere, Samuel Adams, John Hancock, and the victims of the Boston Massacre. As you continue deeper into the heart of Boston, discover why the Freedom Trail was created in the first place and how Boston’s growing skyline once made its historic sites increasingly difficult to navigate. Along the way, your guide will share some of the city’s quirky stories that aren't always shared in the guidebooks, including a legendary alley, a stolen grasshopper-topped time capsule, and where the infamous Ponzi scheme began.
Next, head into Boston’s historic Blackstone Block where you'll be surrounded by some of the oldest continuously operating restaurants in the country. Learn about the traditions born out of Union Oyster House, then enter one of America’s oldest taverns to sample one of our city's most iconic and mouth-watering dishes: A New-England style lobster roll on a toasted bun, served traditionally with a house-made slaw and crispy french fries.
Your final stop is one of Boston’s most famous hotels where you’ll taste the dessert that put the city on the culinary map: Boston Cream Pie. Learn why this cake is called a “pie,” how it was invented here in the 19th century, and why its chocolate topping was such a luxurious addition in its day.
Want to take the experience one step further? Upgrade your tour to include a local craft beer tasting at two of Boston’s most historic taverns, pairing classic Boston foods with the city’s brewing traditions.
Come hungry and curious—you’ll leave with a full stomach, a taste of Boston’s most iconic dishes, and a whole new perspective on the Freedom Trail!
