Boston's Food & History: North End, Freedom Trial, Beacon Hill
Intrepid Urban Adventures - USA
4.9
elli0tt25
3 days ago
Claire was incredibly informative and attentive to our needs. She absolutely fulfilled her mission of sharing local North Boston foodie secrets with us ! For the history portion we covered everything from the big stops on the Freedom Trail to the lovely cobblestoned lanes of Beacon Hill. Highly recommend.
Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza, and a classic Italian deli sandwich. Visit a legendary church, stroll the Freedom Trail, and soak in stunning views from Boston Harbor to charming Beacon Hill. With a local guide leading the way, experience the Boston you’ve always dreamed of—authentic, delicious, and unforgettable.
Departure Point
- Please meet outside the main public entrance of the Boston RMV Service Center, located at 156 Blackstone Street. The RMV is in the same building as the Boston Public Market and sits directly across from the Rose Kennedy Greenway.
Look for the glass-and-metal awning that extends over the sidewalk.
Return Details
- Boston Public Garden (or nearby), 4 Charles St., Boston, MA 02116
Duration
5 hours
Languages Available
- Human tour guide - English
Points of Interest
Stop At: Greenway Carousel
The Tiffany & Co. Foundation Grove, Rose Kennedy Greenway, Boston, Massachusetts
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. Your experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the 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 early 1700s.
Duration: 5 minutes
Stop At: Rose Fitzgerald Kennedy Greenway
Atlantic Ave, , Boston, Massachusetts
We will pass by the Rose Fitzgerald Kennedy Greenway, a linear park located in several Downtown Boston neighborhoods. It consists of landscaped gardens, promenades, plazas, fountains, art, and specialty lighting systems.
Duration: Not Available
Stop At: North End
, , Boston, Massachusetts
Immerse yourself in the heart of Boston’s North End, where history and flavor come together. Start at a hidden Italian bakery, famous for its fresh, crusty bread made daily—a true neighborhood staple. Then, step into a traditional Italian salumeria and indulge in a classic deli sandwich layered with premium cured meats and cheeses, just like locals enjoy. Finally, take a mid-tour break at a bustling Hanover Street café, sipping an authentic Italian coffee while soaking up the lively atmosphere of this iconic corridor. This stop is a delicious journey through the North End’s culinary heritage.
Duration: 1 hour and 20 minutes
Stop At: Old North Church & Historic Site
193 Salem St, , Boston, Massachusetts
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. The Old North Church is closed until the beginning of April. During this time, we will not be able to visit inside the church, but we will stop outside of it.
Duration: 15 minutes
Stop At: Downtown Crossing
Washington Street, , Boston, Massachusetts
A short trek through Downtown Crossing
Duration: Not Available
Stop At: Custom House Tower by Marriott Vacation Club
3 McKinley Square, Boston, MA 02109
From Faneuil Hall, you’ll be able to see Custom House Tower, the first skyscraper built in the city of Boston and originally the location where incoming goods were stored upon arrival to Boston.
Duration: Not Available
Stop At: Old State House
310 Washington Street, , Boston, Massachusetts
Moving into the heart of Downtown Boston, we stop in front of the Old State House. This is where the Declaration of Independence was announced to elated crowds in July 1776 - your guide will paint quite the picture for you of that exciting time in Boston. On the flip side, you’ll also hear about the tragic Boston Massacre that occurred here and what led up to that fateful day.
Duration: 5 minutes
Stop At: Old South Meeting House
310 Washington St, , Boston, Massachusetts
You can’t come to Boston and not mention the Boston Tea Party. While at this stop, which was originally a church, your guide will fill you in on all that led up to the infamous event. Learn who said “No taxation without representation!” and how Bostonians planned their act of rebellion in 1773.
Duration: 5 minutes
Stop At: Old Corner Bookstore
283 Washington St, , Boston, Massachusetts
Next we’ll pass by the site of the first bookstore in Boston, which has housed the publishers of Thoreau’s Walden, Hawthorne’s The Scarlet Letter, and Longfellow - you may have heard of his famous tale: Midnight Ride of Paul Revere.
Duration: Not Available
Stop At: Old City Hall
45 School St, , Boston, Massachusetts
This hall was home to the city council in the 19th and 20th century, as well as the site of the first public school in America. You’ll also marvel at its breathtaking French architecture and be able to snap a photo with the famed Bronze Donkey.
Duration: 10 minutes
Stop At: King's Chapel
58 Tremont St, Boston, Massachusetts
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. Your guide will teach you about its history and its progression through the centuries. If we're lucky, we could hear the organist practicing on the oldest church organ in the US.
Duration: 20 minutes
Stop At: Granary Burying Ground
Tremont Street, Boston, Massachusetts
Originally part of Boston Common, this cemetery dates back to 1660. Along the way, you’ll pass by the final resting spot of famous Revolutionary heroes like John Hancock, Paul Revere, and Sam Adams.
Duration: 10 minutes
Stop At: Boston Common
139 Tremont St, , Boston, Massachusetts
The oldest city park in the United States, Boston Common (not Commons) is a favorite with locals and visitors alike. Walking through the park, you’ll see various memorials, fountains, and recreation areas - which have been enjoyed daily since 1634.
Duration: 15 minutes
Stop At: Beacon Hill
Boston, Massachusetts
One of the most popular and well-known neighborhoods in all of Boston, this area wasn’t always as attractive as it is today. You’ll peek down the cobbled streets as your guide shares the fascinating history of this area - how sailors and British soldiers in the 17th and 18th centuries actually decreased its favor for local residents and how it became the iconic and aspirational neighborhood it is today.
Duration: Not Available
Stop At: Robert Gould Shaw and the 54th Regiment Memorial
Corner of Beacon Street & Park Street, Boston, Massachusetts
A lesser-known memorial, but one of great interest and significance. This memorial commemorates one of the first African American regiments in the Civil War and their colonel Robert Gould Shaw.
Duration: Not Available
Stop At: Massachusetts State House
24 Beacon St, Boston, Massachusetts
You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House. You may have heard of the original landowner for this site, John Hancock, and the man who presided over the cornerstone ceremony for the building in 1795, Paul Revere. Your guide will be sure to fill you in on how this building has lasted over the years and continues to be an integral part of the state’s government.
Duration: 10 minutes
Stop At: Boston Public Garden
4 Charles St, , Boston, Massachusetts
This garden is full of life with residents of modern Boston enjoying it for walks, exercise, fun, or just a peaceful moment. But as you walk through this picturesque park (the first public park in America), you’ll really be able to get a sense of how the land was used by Bostonians (and even British soldiers) throughout the revolution-era and since then as well. Your tour will end here - in the perfect central location for you to continue your day in Boston.
Duration: 15 minutes
Additional Information
- Wheelchair accessible
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- Suitable for all physical fitness levels
- Can this tour accommodate dietary requirements? Absolutely. We can cater for vegetarian, vegan, and gluten-free options. Please notify us at least 24 hours before the tour start time if you have any dietary requests. While we do our best to accommodate these needs, substitutions may not be identical to the original menu items.
- Is this tour environmentally friendly? Unlike many Boston tours that use buses or other vehicles, this experience is entirely on foot—making it a more sustainable choice.
- How does this tour support the local community? In the North End, all food stops are 100% owned and operated by locals, ensuring your visit directly benefits the community. Any inclusions and additional purchases you make help support local businesses.
- Do we visit any historic sites? You’ll stop at the world-famous Old North Church, a non-profit organization dedicated to preserving American history and educating visitors. Your entrance fee helps maintain the church and its educational programs.
- Can the route or inclusions change? We reserve the right to adjust the route and places visited. Food inclusions may vary depending on availability on the day.
- Is the tour suitable for all fitness levels? Yes, but please note the tour involves approximately 8 km (5 miles) of walking.
- Is this tour child-friendly? Yes! This tour is suitable for families. Children under 4 years old can join free of charge. A reduced child price applies for children aged 4 to 11.
- Indulge in one food and drink stop with a hot Italian beverage and pastry in Boston’s North End
- Walk Boston’s famous Freedom Trail and uncover stories of the American Revolution
- Enjoy three food stops featuring fresh North End bread, pizza, and an Italian deli sandwich
- Visit the historic Old North Church, a Freedom Trail icon (entry when available)
- Get tips on what else to see, do and eat during your stay
- Explore Beacon Hill’s charming red-brick streets and classic Boston architecture
- Take in scenic views of Boston Harbor and the Rose Kennedy Greenway
Exclusions
- Tips/gratuities for your guide
- Additional food and drink
Redemption Instructions
Meeting point: Boston RMV Service Center, 156 Blackstone St, Boston, MA.
Meet outside the main public entrance of the Boston RMV Service Center, located in the same building as the Boston Public Market, directly across from the Rose Kennedy Greenway.
Guests should look for the glass-and-metal awning over the sidewalk, directly beside the Surface Rd & Hanover St bus stop. The entrance has a “Massachusetts Department of Transportation” sign above it.
Drop Off Information
Your tour will conclude in a different part of Boston, more than a mile away. We recommend walking, taking public transit, or taking a taxi to get to the meeting point for your tour. If you need to return to the starting location, your guide will be happy to provide general directions.
In the event of a site closure, we will do our best to replace it with a similar alternative.
Dress Code
Comfortable shoes for walking are recommended.
Dietary Information
On this tour we can accommodate vegetarian, vegans, and gluten free options. Please notify us in advance at least 24 h before the tour start time if you have any dietary requests.
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.
Weather
Experience happens rain, shine, or snow unless such weather constitutes a dangerous situation.
Child Policy
Please inform us if you’ll be bringing a child under the age of 6.
Tipping Your Guide
A tip / gratuity for your guide is not included in the price of this tour. If you feel that your guide has done their best to provide a personal and engaging experience, giving a gratuity is encouraged.
Review us
How did we do? Your experience matters! Let us know by leaving a review.
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Intrepid Urban Adventures - USA in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza, and a classic Italian deli sandwich. Visit a legendary church, stroll the Freedom Trail, and soak in stunning views from Boston Harbor to charming Beacon Hill. With a local guide leading the way, experience the Boston you’ve always dreamed of—authentic, delicious, and unforgettable.
Departure Point
- Please meet outside the main public entrance of the Boston RMV Service Center, located at 156 Blackstone Street. The RMV is in the same building as the Boston Public Market and sits directly across from the Rose Kennedy Greenway.
Look for the glass-and-metal awning that extends over the sidewalk.
Return Details
- Boston Public Garden (or nearby), 4 Charles St., Boston, MA 02116
Duration
5 hours
Languages Available
- Human tour guide - English
Points of Interest
Stop At: Greenway Carousel
The Tiffany & Co. Foundation Grove, Rose Kennedy Greenway, Boston, Massachusetts
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. Your experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the 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 early 1700s.
Duration: 5 minutes
Stop At: Rose Fitzgerald Kennedy Greenway
Atlantic Ave, , Boston, Massachusetts
We will pass by the Rose Fitzgerald Kennedy Greenway, a linear park located in several Downtown Boston neighborhoods. It consists of landscaped gardens, promenades, plazas, fountains, art, and specialty lighting systems.
Duration: Not Available
Stop At: North End
, , Boston, Massachusetts
Immerse yourself in the heart of Boston’s North End, where history and flavor come together. Start at a hidden Italian bakery, famous for its fresh, crusty bread made daily—a true neighborhood staple. Then, step into a traditional Italian salumeria and indulge in a classic deli sandwich layered with premium cured meats and cheeses, just like locals enjoy. Finally, take a mid-tour break at a bustling Hanover Street café, sipping an authentic Italian coffee while soaking up the lively atmosphere of this iconic corridor. This stop is a delicious journey through the North End’s culinary heritage.
Duration: 1 hour and 20 minutes
Stop At: Old North Church & Historic Site
193 Salem St, , Boston, Massachusetts
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. The Old North Church is closed until the beginning of April. During this time, we will not be able to visit inside the church, but we will stop outside of it.
Duration: 15 minutes
Stop At: Downtown Crossing
Washington Street, , Boston, Massachusetts
A short trek through Downtown Crossing
Duration: Not Available
Stop At: Custom House Tower by Marriott Vacation Club
3 McKinley Square, Boston, MA 02109
From Faneuil Hall, you’ll be able to see Custom House Tower, the first skyscraper built in the city of Boston and originally the location where incoming goods were stored upon arrival to Boston.
Duration: Not Available
Stop At: Old State House
310 Washington Street, , Boston, Massachusetts
Moving into the heart of Downtown Boston, we stop in front of the Old State House. This is where the Declaration of Independence was announced to elated crowds in July 1776 - your guide will paint quite the picture for you of that exciting time in Boston. On the flip side, you’ll also hear about the tragic Boston Massacre that occurred here and what led up to that fateful day.
Duration: 5 minutes
Stop At: Old South Meeting House
310 Washington St, , Boston, Massachusetts
You can’t come to Boston and not mention the Boston Tea Party. While at this stop, which was originally a church, your guide will fill you in on all that led up to the infamous event. Learn who said “No taxation without representation!” and how Bostonians planned their act of rebellion in 1773.
Duration: 5 minutes
Stop At: Old Corner Bookstore
283 Washington St, , Boston, Massachusetts
Next we’ll pass by the site of the first bookstore in Boston, which has housed the publishers of Thoreau’s Walden, Hawthorne’s The Scarlet Letter, and Longfellow - you may have heard of his famous tale: Midnight Ride of Paul Revere.
Duration: Not Available
Stop At: Old City Hall
45 School St, , Boston, Massachusetts
This hall was home to the city council in the 19th and 20th century, as well as the site of the first public school in America. You’ll also marvel at its breathtaking French architecture and be able to snap a photo with the famed Bronze Donkey.
Duration: 10 minutes
Stop At: King's Chapel
58 Tremont St, Boston, Massachusetts
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. Your guide will teach you about its history and its progression through the centuries. If we're lucky, we could hear the organist practicing on the oldest church organ in the US.
Duration: 20 minutes
Stop At: Granary Burying Ground
Tremont Street, Boston, Massachusetts
Originally part of Boston Common, this cemetery dates back to 1660. Along the way, you’ll pass by the final resting spot of famous Revolutionary heroes like John Hancock, Paul Revere, and Sam Adams.
Duration: 10 minutes
Stop At: Boston Common
139 Tremont St, , Boston, Massachusetts
The oldest city park in the United States, Boston Common (not Commons) is a favorite with locals and visitors alike. Walking through the park, you’ll see various memorials, fountains, and recreation areas - which have been enjoyed daily since 1634.
Duration: 15 minutes
Stop At: Beacon Hill
Boston, Massachusetts
One of the most popular and well-known neighborhoods in all of Boston, this area wasn’t always as attractive as it is today. You’ll peek down the cobbled streets as your guide shares the fascinating history of this area - how sailors and British soldiers in the 17th and 18th centuries actually decreased its favor for local residents and how it became the iconic and aspirational neighborhood it is today.
Duration: Not Available
Stop At: Robert Gould Shaw and the 54th Regiment Memorial
Corner of Beacon Street & Park Street, Boston, Massachusetts
A lesser-known memorial, but one of great interest and significance. This memorial commemorates one of the first African American regiments in the Civil War and their colonel Robert Gould Shaw.
Duration: Not Available
Stop At: Massachusetts State House
24 Beacon St, Boston, Massachusetts
You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House. You may have heard of the original landowner for this site, John Hancock, and the man who presided over the cornerstone ceremony for the building in 1795, Paul Revere. Your guide will be sure to fill you in on how this building has lasted over the years and continues to be an integral part of the state’s government.
Duration: 10 minutes
Stop At: Boston Public Garden
4 Charles St, , Boston, Massachusetts
This garden is full of life with residents of modern Boston enjoying it for walks, exercise, fun, or just a peaceful moment. But as you walk through this picturesque park (the first public park in America), you’ll really be able to get a sense of how the land was used by Bostonians (and even British soldiers) throughout the revolution-era and since then as well. Your tour will end here - in the perfect central location for you to continue your day in Boston.
Duration: 15 minutes
Additional Information
- Wheelchair accessible
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- Suitable for all physical fitness levels
- Can this tour accommodate dietary requirements? Absolutely. We can cater for vegetarian, vegan, and gluten-free options. Please notify us at least 24 hours before the tour start time if you have any dietary requests. While we do our best to accommodate these needs, substitutions may not be identical to the original menu items.
- Is this tour environmentally friendly? Unlike many Boston tours that use buses or other vehicles, this experience is entirely on foot—making it a more sustainable choice.
- How does this tour support the local community? In the North End, all food stops are 100% owned and operated by locals, ensuring your visit directly benefits the community. Any inclusions and additional purchases you make help support local businesses.
- Do we visit any historic sites? You’ll stop at the world-famous Old North Church, a non-profit organization dedicated to preserving American history and educating visitors. Your entrance fee helps maintain the church and its educational programs.
- Can the route or inclusions change? We reserve the right to adjust the route and places visited. Food inclusions may vary depending on availability on the day.
- Is the tour suitable for all fitness levels? Yes, but please note the tour involves approximately 8 km (5 miles) of walking.
- Is this tour child-friendly? Yes! This tour is suitable for families. Children under 4 years old can join free of charge. A reduced child price applies for children aged 4 to 11.
- Indulge in one food and drink stop with a hot Italian beverage and pastry in Boston’s North End
- Walk Boston’s famous Freedom Trail and uncover stories of the American Revolution
- Enjoy three food stops featuring fresh North End bread, pizza, and an Italian deli sandwich
- Visit the historic Old North Church, a Freedom Trail icon (entry when available)
- Get tips on what else to see, do and eat during your stay
- Explore Beacon Hill’s charming red-brick streets and classic Boston architecture
- Take in scenic views of Boston Harbor and the Rose Kennedy Greenway
Exclusions
- Tips/gratuities for your guide
- Additional food and drink
Redemption Instructions
Meeting point: Boston RMV Service Center, 156 Blackstone St, Boston, MA.
Meet outside the main public entrance of the Boston RMV Service Center, located in the same building as the Boston Public Market, directly across from the Rose Kennedy Greenway.
Guests should look for the glass-and-metal awning over the sidewalk, directly beside the Surface Rd & Hanover St bus stop. The entrance has a “Massachusetts Department of Transportation” sign above it.
Drop Off Information
Your tour will conclude in a different part of Boston, more than a mile away. We recommend walking, taking public transit, or taking a taxi to get to the meeting point for your tour. If you need to return to the starting location, your guide will be happy to provide general directions.
In the event of a site closure, we will do our best to replace it with a similar alternative.
Dress Code
Comfortable shoes for walking are recommended.
Dietary Information
On this tour we can accommodate vegetarian, vegans, and gluten free options. Please notify us in advance at least 24 h before the tour start time if you have any dietary requests.
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.
Weather
Experience happens rain, shine, or snow unless such weather constitutes a dangerous situation.
Child Policy
Please inform us if you’ll be bringing a child under the age of 6.
Tipping Your Guide
A tip / gratuity for your guide is not included in the price of this tour. If you feel that your guide has done their best to provide a personal and engaging experience, giving a gratuity is encouraged.
Review us
How did we do? Your experience matters! Let us know by leaving a review.
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Intrepid Urban Adventures - USA in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
Need To Know Info
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and SavingsFrequently Asked Questions
Customer Reviews
4.9
based on Groupon 1,774 reviews
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Reviewed on
elli0tt25
Claire was incredibly informative and attentive to our needs. She absolutely fulfilled her mission of sharing local North Boston foodie secrets with us ! For the history portion we covered everything from the big stops on the Freedom Trail to the lovely cobblestoned lanes of Beacon Hill. Highly recommend.
C7924KTtravisp
Fun and informative tour. The foods were delicious. Bob was very personable and made the experience very memorable!
easanders
My husband and I had a wonderful experience on this tour with Lexie, even on a very rainy day during our visit to Boston (first time). She was incredibly knowledgeable about the city’s history and added thoughtful personal touches by sharing stories from her own upbringing in the area. The food portions were generous and we could barely finish everything.
What truly stood out was Lexie’s kindness. She reached out the morning of the tour, despite the downpour and the fact that all other participants had canceled, and still met us in the rain to make sure we enjoyed our day.
I highly recommend this tour as a fantastic way to experience Boston’s rich history and delicious food in one memorable outing. This was very helpful on a trip with a packed itinerary.
renk942
I had an amazing tour with Bob today! It was very cold and windy, but bundle up and don’t let that deter you!! Bob took me for some delicious treats at beloved local spots in the North End, giving fabulous history lessons of everywhere we stopped. By the end of the food tour I was stuffed. Then we had the history portion of the tour, walking part of the freedom trail. Bob was knowledgeable and compelling. Finally, we stopped for cider and walked through classic Boston stops - Beacon Hill (incl Acorn Street), the Common and the Public Garden. Bob kindly followed up with an email recap of our day and some suggestions for where we could go out to eat for the rest of our stay in Boston - specifically tailored to our preferences. Can’t recommend enough!
deedeec918
Nabil was awesome! He took us to some amazing food places and showed us little hideaways in the city. He explained the history and made it fun! Highly recommend.