From Food to Freedom Trail

Discover the local side of Boston’s most popular neighborhood, the North End.  Visit Boston’s most revered church and snack your way through the neighborhood, tasting meats, cheeses, fresh bread, pastries, pizza and cappuccino. Continue along the Freedom Trail and beyond and experience modern Boston through the city’s incredible history. From the iconic Boston Harbor, into the heart of beautiful Beacon Hill, join your local guide on an experience that connects you to the Boston of old and new.

Your North End to the Freedom Trail combines our North End Food Tour and our History and Highlights Tour to make up a brilliant half day tour that will give you a comprehensive introduction to our fair city.   

We will begin at the lifeblood of Boston, the Boston Harbor, with a walk through a scenic waterfront park, with views of the harbor, East Boston and historic wharfs lining Atlantic Ave. We’ll make our way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and 1700s. 

Tasty food is never far away in the North End. Your guide will introduce you to a small, hidden Italian bakery serving up fresh bread daily. A proper Italian salumeria is next, where you’ll have a chance to enjoy some Italian meats and cheeses at their finest and freshest. 

Next up, we’ll take in the energy of the North End’s busiest corridor, Hanover Street, where it’s time for a mid-tour break with your guide at a traditional Italian café. Here, if you like, you can purchase and enjoy your choice of a classic cappuccino, espresso or tea or just take a minute off your feet.

As you let the caffeine kick in, your guide goes back in time into North End history. Hear stories about some of the most influential events that happened in Boston, including Paul Revere’s Midnight Ride. We make our way to the Old North Church, where we may get to step inside the hallowed walls.

After church, we’ll dive deeper into the local side of the North End. A taste of pizza awaits at a neighborhood favorite and then we’ll cap off the North End food experience with samples of the best Italian pastries along the back streets of this delicious neighborhood. Hopefully there will be a chance to meet and chat with the area’s best bakers, if we catch them at a quiet moment. 

Continue on with your guide beyond the North End neighborhood for a leisurely stroll through some of Boston’s best markets and green spaces. You’ll begin the second part of your journey back at the Aquarium “T” Station where we’ll meet more members of the group. From the Harbor, we’ll continue past the Rose Kennedy Greenway, State Street and the historic Custom House Tower, the city’s first skyscraper. Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views. 

Moving into the heart of Downtown Boston, we will stop in front of the Old State House and site of the Boston Massacre. Was it really a massacre or maybe just great propaganda for the Revolution? Ask your expert guide about that one! 

A short trek through Downtown Crossing and past the Old City Hall takes you to one of the most historic places in the country - King’s Chapel, the first Anglican church in New England. Whenever possible, your guide takes you inside, to see the first church in the US to have a pipe organ. If we’re lucky, we might just get to hear it being played.

On most weekdays (government hours only!) you have a chance to see the government at work inside the inspiring, historic, and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. Outside the State House, take in the views of modern Boston, including the skyscrapers of Downtown, the Financial District, and the tallest building in New England: The John Hancock Tower.

We continue our journey through Beacon Hill, where you’ll have a chance to take in the quintessential architecture of Boston’s red brick row houses. Get out your cameras — this neighborhood is one of the most photogenic in the city. 

Finally, we’ll arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces, where you’ll see locals walking the dogs, playing with the kids and enjoying lunch in the shade. Your guide will point you in the right direction, and will help with any and all recommendations for great things to do in Boston that evening and beyond.