From Food to Freedom Trail

Operated By: Urban Adventures Boston

Activity Description

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.

From Food to Freedom Trail Highlights

  • Take in the beauty of the architecture and quaintness of Beacon Hill
  • Learn the modern impact of Boston's most iconic historic sights
  • Enjoy a beer and some tasty snacks at some of our favorite local haunts
  • Stroll past some of the most historic locations in Boston's oldest neighborhood
  • Join your local guide for a fun-filled journey on and off Boston's famous Freedom Trail


Local English-speaking guide, a variety of food samples such as fresh bread, pizza, and pastries, entrance fee to the historic church, and one beer (or non-alcoholic beverage of your choice).


Additional food and drink, souvenirs, and tips/gratuities for your guide.


Meeting point: The Aquarium "T" Station (Outside, in front of the Long Wharf Entrance - Northeast Corner of State St. and Atlantic Ave.) 222 State Street, Boston, MA 02109. View on Google Maps.

Ending point: Boston Public Garden (or nearby), 4 Charles St., Boston, MA 02116

Starting time: 10.00 AM

Duration: 5 hours

  Full Itinerary

We continue our journey through Beacon Hill, where you 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.

Moving into the heart of Downtown Boston, we 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!

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

Next up, we 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, you have a chance to enjoy your choice of a classic cappuccino, espresso, or tea.

We 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 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.

Closure of sites: In the event of a site closure, we will do our best to replace it with a similar alternative.

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 gives you a comprehensive introduction to our fair city.

On most weekdays, you have a chance to see the government at work (or not) 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.

Confirmation of booking: If you have your voucher, your booking is confirmed. We'll see you at the start point. Get in touch if you have any concerns or require more information via the email address or phone number (business hours only) on your voucher.

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

Inclusions: Local English-speaking guide, a variety of food samples such as fresh bread, pizza, and pastries, entrance fee to the historic church, and one beer (or non-alcoholic beverage of your choice).

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 and step inside the hallowed walls.

Exclusions: Additional food and drink, souvenirs, and tips/gratuities for your guide.

Your Trip: For your Urban Adventure you will be in a small group of a maximum of 12 people.

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 Burial Ground (city's oldest burial ground) and King's Chapel (the first Anglican church in the country). Whenever possible, your guide takes you inside King's Chapel, the first church in the USA to have a pipe organ. If we're lucky, we might just get to hear it being played.

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

Somewhere along the way during this tour, you have a chance to rest your legs and enjoy a refreshing local beer. Your guide chooses among some of the most historic, quirky, and hidden local bars and taverns in the area.

Child Policy: This is a child-friendly tour. Children between the ages of six and 11 inclusively are permitted on this tour at the rate listed above. Please select 'child' above when booking. Children under the age of six are permitted to join this tour free of charge. Please inform us at the time of booking if you'll be bringing a child under the age of six. You can do so in the special request box on the checkout page.

Office phone number: + 1 617 539 8271 Email address:

Additional Information: Entrance to the Massachusetts State House requires a government ID and all guests must pass through metal detectors. The State House is open on weekdays only, we will find alternate sites to visit on weekends.

We can accommodate vegetarians and other dietary restrictions. Please notify us in advance if you have any dietary requests. You can do so in the 'Additional information' box at checkout, or by emailing us at

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 begin the second part of your journey back at the Aquarium "T" Station where we meet more members of the group. From the Harbor, we continue past the Rose Kennedy Greenway, State Street, and the historic Custom House Tower, the city's first skyscraper. Then, your guide leads you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views.

Phone Number: 617-539-8271
Average Time: 5 hours
Difficulty: Beginner

Location - The Aquarium “T” Station



No Comments for this product

Please login to leave a review

Create a New Reservation

Search for availability

Related Products