Pubs of the Freedom Trail The Crawl to Liberty

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2 hours (approximately)
Offered in: English

Explore Boston’s history with a spirited twist on the Freedom Trail. This lively walking tour blends sharp colonial storytelling with a pub crawl through several of Boston’s most iconic bars. Led by a costumed guide with a talent for good‑natured mischief, you’ll enjoy curated half‑pours of beer or cider at each stop, each chosen to match the landmark and the legend right outside. The tour kicks off at Democracy Brewing and wraps up at either its Beer Garden or The Black Rose, depending on the season. With a two hour run time, it’s a relaxed, rowdy way to raise a glass to Boston’s past.
Visit multiple historic pubs along Boston's Freedom Trail
Enjoy curated half‑pints at every stop
Hear engaging stories tied to nearby landmarks
Costumes aren’t required, but they’re absolutely encouraged (and frequently roasted).

What's Included

Each stop features a curated half‑pint of beer or cider, selected to complement the history explored at that location, highlighting each site’s character through taste and tradition.

Meeting and pickup

Meeting point
Democracy Brewing

located at 35 Temple Place in Downtown Boston. It is an easy walk from the Park Street or Downtown Crossing stations. Guests should enter through the main Temple Place entrance. Your guide will be waiting inside the front area in full colonial costume, making us easy to spot.

End point
This activity ends in a different location. You can choose from multiple locations at checkout.

Itinerary

Duration: 2 hours (approximately)
  • Boston Common (Pass by)

    Boston Common is America’s oldest public park, a central landmark in downtown Boston and the sute that begins our story of colonial Boston. Viewed from Democracy Brewing.

    Admission ticket free
  • Massachusetts State House (Pass by)

    The New State House overlooks Beacon Hill and marks a key moment in Boston’s political growth. It is discussed at Emmett’s Pub as we continue our story of colonial Boston and its lasting legacy.

    Admission ticket free
  • Granary Burying Ground (Pass by)

    Granary Burying Ground is the resting place of key figures from Boston’s revolutionary era and a central part of our colonial story. Viewed from Beantown Pub as we continue the tour.

    Admission ticket free
  • Old South Meeting House (Pass by)

    Old South Meeting House and the Old Corner Bookstore are central landmarks in Boston’s colonial and literary history. Both are discussed from Hub Pub as we continue our story of the city’s revolutionary past.

    Admission ticket free
  • Old State House (Pass by)

    The Old State House is one of Boston’s most important colonial landmarks and the site of the Boston Massacre. It is discussed from the Democracy Brewing Beergarden or The Black Rose as we continue our story of the city’s revolutionary past.

    Admission ticket free
  • Boston Massacre Site (Pass by)

    The Boston Massacre marks a turning point in colonial resistance and is central to our story of rising tensions in 1770. It is discussed at the Democracy Brewing Beergarden as we explore the events leading to revolution.

    Admission ticket free

Additional info

  • Wheelchair accessible
  • Service animals allowed
  • Public transportation options are available nearby
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Not recommended for pregnant travelers
Supplied by Boston Bootleggers and Buccaneers
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Tags

Private and Luxury
Beer & Brewery Tours
Historical Tours
Walking Tours
Food & Drink
Short term availability

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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