Boston Heritage by Foot

    • 3 - 3.5 hours
    • USDS
    • Total price tool tip
    • *Approx package price

Make the most of being in one of America's most walkable cities on this Boston tour that side steps the well known Freedom Trail to see old jailhouses, watering holes, and other notable urban spots you'd otherwise probably miss.


* Ditch the Freedom Trail and join a local for a tour of Boston's most fascinating neighbourhoods

* Listen to local tales of Boston's rich history and past

* Go back in time and be immersed in the West End’s past, including former local farms, jailhouses, and watering holes

* Discover the stories behind Boston's first synagogue

What's included in this trip

  • Start:

    420 Commercial St, Boston, MA 02109
  • Finish:

    420 Commercial St, Boston, MA 02109
  • Group size:

    Min 1 , Max 12
  • Inclusions:

    Local English-speaking guide, drink and snack, admission fees to sites included on tour.
  • Exclusions:

    Items of a personal nature, tips and gratuities for your guide. 

Additional information

Carbon Offset:Voucher exchange details

Please present your voucher to the local guide at the beginning of the tour.

Confirmation of booking

Please contact Boston Urban Adventures to confirm your tour 24 hours prior to departure.

Dress standard

Casual attire and comfortable footwear.

Child policy

Children must be 6 years of age to 11 years inclusively. Children below the age of 6 are not permitted on this tour.



Tipping Info

If you are happy with the services provided by your local guides a tip - though not compulsory - is appropriate. While it may not be customary to you, it is of great significance to the people who will take care of you during your travels, inspires excellent service, and is an entrenched feature of the tourism industry across many Intrepid Urban Adventures destinations. Please consider this when budgeting for your extra expenses on this tour.


Take a hike on this historical Boston tour that takes your of the beaten Freedom Trail and gives you a local snapshot of this beautiful city. This Boston walking tour begins at our Welcome Centre in the North End, Boston’s oldest neighbourhood. From there, we lead you away from the tourist trail and onto the back roads of Boston’s extensive and fascinating urban history.
We'll kick off this Boston tour with a visit to the West End Museum to enlighten you on the pre-landfill project area, the 'Last Tenement Building', urban renewal, and post-war slums. Continuing your immersion into history, we walk on to the site of the Old Suffolk County Jail, where you’ll grab a small bite, and perhaps a drink, and learn about the seedy underbelly of Boston’s old jailhouses and watering holes. This is the side of Boston history you don’t often see, and with a local guide to give you the inside scoop you'll surely come out of this tour with plenty of local info. 
As we continue this Boston city tour, we visit Boston’s first synagogue, which is also the city’s last remaining immigrant-era synagogue. A tour through this historically significant building will give you yet another local historical perspective on Beacon Hill, a very popular Boston neighbourhood.
Your Boston walking tour ends back at the North End Welcome Centre, where you will return full of local knowledge, local experiences, and stories of local history that you won’t find following a stuffy guide with a flag and a microphone! 

Book this trip