Boston History & Highlights


Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history. From the iconic Boston Harbor, to the famous Freedom Trail, into the heart of beautiful Beacon Hill, join your local guide on an experience that promises to connect you to the Boston of old and new.

History of Boston Walking Tour Highlights

  • Join your local guide for a fun-filled journey on and off Boston’s famous Freedom Trail
  • Learn the modern impact of Boston’s most iconic historic sights
  • Explore the inside of some of the sights overlooked by many Boston visitors (and even locals!)
  • Take in the beauty of the architecture and quaintness of Beacon Hill
  • Enjoy a beer with your guide inside one of their favorite neighborhood watering holes

Inclusions: Local English-speaking guide, and one beer (or non-alcoholic beverage of your choice).

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

Schedule details

  • Duration: 2 hours
  • 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.
  • Starting time: 1.00 PM
  • Ending point: Boston Public Garden (or nearby), 4 Charles St., Boston, MA 02116
  • Chevron down Full Itinerary
  • Your experience begins at the Aquarium “T” Station on the historic Long Wharf, the focus of Boston Harbor, and the economic engine of Boston for most of its history. 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.

    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!

    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 US to have a pipe organ. If we’re lucky, we might just get to hear it being played.

    Somewhere along the way during this Boston walking 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.

    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.

    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.

    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.

    Additional information

    Inclusions: Local English-speaking guide, and one beer (or non-alcoholic beverage of your choice).

    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.

    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.

    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, and we will find alternate sites to visit on weekends.

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

    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.

    Local contact

    Office phone number: + 1 617 539 8271
    Email address: [email protected]

  • Chevron down Reviews
  • Mrs. Mary M. from USA traveled on 13 Jun 2018:

    Bob was a great tour guide. His enthusiasm for Boston and it’s history and culture was great. He knows his stuff. We really liked the restaurants he recommended. Very Good. Even though Urban Adventures is just getting started in this market, Bob’s an expert.