Discover Boston's Cuisine and History on a Yummy Walks Food Tour

When travelers picture Boston, they probably think of U.S. history and clam chowder — and for good reason. The American Revolution began here, and the city’s 2.5-mile Freedom Trail includes 16 historically significant sites.

As for chowder, the cream-based soup is just one of the city’s well-known dishes. Many other foods have ties to Boston, as well — including the one that gave it the nickname “Beantown”: Boston baked beans.

For clients looking for an intimate Boston experience, travel advisors should book the Foods of the Freedom Trail - The Total Boston Experience walking tour from Yummy Walks, says Darlyn Gagnon, manager and co-owner of the local food tour operator. 

“Walk the neighborhoods with an experienced local guide, learn the history, and stop for foods that represent the area and culture,” she said.

The approximately three-hour tour starts at Boston Common — America’s oldest public park — and visits 12 Freedom Trail sites, tracing U.S. history alongside Boston’s culinary history. (The Freedom Trail is a 2.5-mile path through downtown Boston that leads visitors to 16 historically significant U.S. sites.) Stops include some of the city’s oldest spots, such as Durgin-Park, one of Boston’s oldest and continuously operating restaurants; and Union Oyster House, which is housed in a building that dates back to Pre-Revolutionary War days. (Yummy Walks Foods of the Freedom Trail costs $58 for adults and $35 for children under 12.)

However, the tour also includes some of Boston’s modern culinary standouts, such as Mooo, an upscale restaurant that is steps away from the Massachusetts State House; Sweet Bakery, which was awarded “Boston’s Best Cupcakes” three years in a row; and Corner Stalk Farm, a hydroponic farm growing greens in recycled shipping containers.

“The Freedom Trail is a great way to learn about Boston’s history — and our country’s history — because it connects everything,” said Chloe Hill, a tour guide for Yummy Walks. “And all the food on the tour is related to Boston’s history in some way.”

The first food stop was Mooo for lobster bisque. Hill explained to our group that lobster was so overabundant during colonial times that giving it to prisoners more than three times per week was considered cruel and unusual punishment. Thankfully, lobster is now considered a delicacy. 

“We come to Mooo because they’ve gained quite a reputation for their bisque,” Hill said. “Most bisques are very heavy, but here, they use light cream and sherry with chunks of lobster, so it’s a refined and unique bisque.”

After our delicious sampling, we went out Mooo’s back door and found ourselves at the Granary Burying Ground, the third oldest graveyard in Boston. Many famous Revolutionary patriots are buried here, including John Hancock, one of the Founding Fathers of the U.S. and the first to sign the Declaration of Independence; Samuel Adams, who, along with Benjamin Franklin, was an architect of the Revolutionary War; and Paul Revere, who is perhaps the most famous Revolutionary War-era patriot.

As we continued our tour, we passed Omni Parker House, the former site of Parker House Hotel. This is where former president John F. Kennedy proposed to former first lady Jacqueline Kennedy Onassis, and it’s also where Boston cream pie was invented. Incidentally, it’s not pie at all, but rather yellow cake with a custard filling and a chocolate ganache frosting. At Sweet Bakery, we tried what’s considered to be the perfect Boston cream pie cupcake due to its ratio of cake to custard and frosting. 

We headed to Durgin-Park restaurant for turkey with Boston baked beans, cranberry sauce and cornbread, and on the way, we walked past the Old State House, the oldest building in Boston and where the Declaration of Independence was read after the Revolution (and is still read every Fourth of July). 

Hill explained that the foods we were to eat are all tied to Boston’s history through the Native Americans. Corn, a Native American staple when the colonists arrived, was substituted in wheat-based recipes; similarly, Native Americans used cranberries, but Revolutionary War patriot Henry Hall first cultivated them. As for Boston baked beans, colonists adopted them from a Native American recipe, but instead of cooking them with maple syrup and bear or venison fat, they used brown sugar or molasses and bacon.

Our next stop was the relatively new Boston Public Market, an indoor farmers market that features locally made, artisanal foods and fresh produce. One of the market’s vendors is Red Apple Farms, a more than 100-year-old farm northwest of Boston. Here, we tried delicious apple-cider-infused donuts, which have a colonial history because the Puritans brought the art of donut-making to the colonies.

Also in Boston Public Market is Corner Stalk Farm, an urban farm in East Boston known for growing greens in shipping containers. However, we were there to taste shrubs, which are fruit-infused drinking vinegars. Shrubs were common during colonial times to preserve fruit during winter, but the fruit also infused the vinegar, so colonists would use that for cooking, baking and drinking. We sampled shrub flavors such as sour cherry plum, cranberry tangerine and, the most popular, raspberry bergamot.

“People use shrubs for drinking with alcohol or for mocktails,” said Dana, a representative from Corner Stalk Farm. “They’re also great over fresh fruit, in salad dressings or to flavor sparkling water.”

The final stop was Union Oyster House, which is located in the building that once housed “The Massachusetts Spy” (a Pre-Revolutionary War newspaper). Union Oyster House patrons have included former U.S. politician Daniel Webster and JFK, whose regular table upstairs is called the Kennedy table. 

Here, we tried Indian pudding based on British hasty pudding, made of wheat flour, butter, eggs, milk, molasses and spices such as cloves, cinnamon, ginger and nutmeg. When colonists substituted cornmeal — or Indian meal — for wheat flour, it became Indian pudding. I thought the pudding tasted like sweet, spiced Cream of Wheat, but Hill told me it has also been described as liquefied ginger bread or uncooked pumpkin pie filling. 

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