Pubs of the Freedom Trail The Crawl to Liberty

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).

1. 1

   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.

2. 2

   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.

3. 3

   Stop 3

   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.

4. 4

   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.

5. 5

   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.

6. 6

   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.

• 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

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