Boston Food & History North End Freedom Trail Walking Tour

5 hours
Free cancellation
1 - 12
Mobile ticket


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.


This is a typical itinerary for this product

Pass By: North End, Boston, MA 02109

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. We’ll make our way to the heart of the North End, with views of some of the most historic sites. 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. 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.

Stop At: Old North Church & Historic Site, 193 Salem St, Boston, MA 02113-1123

You’ll hear stories about some of the most influential events that happened in Boston, including Paul Revere’s Midnight Ride. We will make our way to the Old North Church and step inside the hallowed walls.

Duration: 15 minutes

Pass By: Rose Kennedy Greenway, JFK Surface Road, Boston, MA 02111

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.

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.

Pass By: Marriott's Custom House, 3 McKinley Sq, Boston, MA 02109-2609

See State Street and the historic Custom House Tower, the city’s first skyscraper.

Pass By: Faneuil Hall Marketplace, 1 Faneuil Hall Sq Quincy Market, Boston, MA 02109-1604

Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market.

Pass By: Quincy Market, 206 S Market St, Boston, MA 02109-6201

In downtown Boston

Pass By: Old State House, 206 Washington St, Boston, MA 02109-1702

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?

Pass By: Downtown Crossing, Washington Street, Boston, MA 02111

A short trek through Downtown Crossing

Stop At: Old City Hall, 45 School St, Boston, MA 02108-3206

A short trek through Downtown Crossing brings you to Old City Hall. This beautiful building, done in French Revivalist architecture, was the seat of city government for years in Boston. It also happens to be the site of the birth of public education in America. You'll definitely want to have your guide snap your picture with the bronze donkey outside the entrance.

Duration: 15 minutes

Pass By: Massachusetts State House, 24 Beacon St Beacon Hill, Boston, MA 02133-1099

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.

Pass By: Boston Public Garden, 4 Charles St, Boston, MA 02114-4602

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.


  • Friendly Local, English-speaking guide
  • 3 food stops (with a variety of food samples such as fresh bread, pizza, meats, and cheese)
  • 1 food and drink stop (Hot Italian beverage and Pastry)
  • Entrance fee to the historic Old North Church (or equivalent alternative)
  • Enjoy the stunning views from Faneuil Hall and Quincy Market
  • Learn about the Sons of Liberty and see where the Boston Tea Party took place
  • Enjoy a surprise local treat


  • Tips/gratuities for your guide
  • Additional food and drink

Additional information

  • Confirmation will be received at time of booking
  • Wheelchair accessible
  • 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.
  • This is a child-friendly tour. Children under the age of 6 are permitted to join this tour free of charge.
  • We can accommodate vegetarians and other dietary restrictions. Please notify us in advance if you have any dietary requests.
  • Small group of a maximum of 12 people.
  • Local Impact: How you will help the local community by joining this tour: The Food to Freedom Tour is environmentally friendly because unlike many of the tour companies in Boston, you walk as opposed to using buses or other vehicles.
  • Near public transportation
  • Transportation is wheelchair accessible
  • In the morning when you are in the famous North End, all of the food stops are 100% owned and run by locals, ensuring that local people benefit from tourism to their city. So any inclusions on the tour and additional purchases you make will directly benefit the local community.
  • You also stop at one of the world-famous churches which is as much a part of Boston's (and America's) history as you can get. The Old North Church is a non-profit organization that works hard to educate school children and adults on American history and colonial life. By paying an entrance fee, you are helping to maintain the church and their work.
  • We reserve the right to change both the route and places visited within the tour. Food inclusions are subject to change, dependent on availability on the day.
  • Most travelers can participate
  • This tour/activity will have a maximum of 12 travelers
  • Guides required to regularly wash hands
  • All tours follow the latest local health authority advice. Urban Adventures has received the World Travel and Tourism Council’s Safe Travels stamp, which recognises companies that have adopted health and hygiene global standardised protocols.

Ticket delivery

You can present either a paper or an electronic voucher for this activity.


See Availability


For a full refund, cancel at least 24 hours in advance of the start time of the experience.

May 2022

Our guide Tyler was so informative! We saw so many historic sites on the tour. Great pace, not too slow or too fast. I really enjoyed the small group as we only had 4 people on the tour. It’s much easier to hear our guide and ask questions. Each food stop was phenomenal! I’d highly recommend...

May 2022

Excellent tour! Our guide Tyler provided us with so much historical information! The food at each of our stops was phenomenal! I highly recommend this tour!

May 2022

Thank you! We really enjoyed our tour….Tyler was GREAT! He was so knowledgeable and even sent a follow up email with must see suggestions and restaurant recommendations. Again thanks for the wonderful experience!

May 2022

This was my first time taking a tour around the North End, and it was the highlight of our weekend! Kim was enthusiastic, knowledgeable, friendly and definitely had her audience engaged. We stopped at all of the historical sights in the North End and explored delicious restaurants/shops. Kim answ...

May 2022

Sully was a very knowledgeable tour guide. He knew the history of Boston. We thoroughly enjoyed having a cappuccino, cannoli, Italian sub, pizza, and bread at the places we went to. What I loved was learning the rich history of Boston. I would definitely come back. I wish though our food was spre...

May 2022

This small group format is a wonderful way to cover a lot of territory and history in a relaxed way. Our guide, Campbell, was knowledgeable about the facts and had a number of intriguing anecdotes as well. It was evident that he was fascinated by the material himself, and his enthusiasm added to ...

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from US$98.80 / per person