Charlestown Grit to Glory Walking Tour

Charlestown, Boston, Boston



Explore Charlestown on a guided walking tour. Discover the stories of witches, revolutionaries, and bank robbers, and climb the 294 steps of the Bunker Hill Monument for panoramic views.

Highlights

  • Immerse yourself in the rich history of Charlestown on a guided walking tour
  • Discover the stories of witches, revolutionaries, and bank robbers
  • Explore the hidden alleys and historic streets of this iconic neighborhood
  • End your tour at the oldest tavern in Massachusetts, the Warren Tavern

Description

Begin your walking tour at the USS Constitution, also known as 'Old Ironsides.' Learn about the ship's history and its role in the American Revolution. Next, head to City Square Park and travel back in time to uncover the darker, mystical side of the neighborhood. Hear the story of Margaret Jones, a Charlestown midwife who in 1648 became the very first person executed for witchcraft in the Massachusetts Bay Colony. Bridge the narrative to Goody Glover, the Irish Catholic laundry woman hanged in 1688 whose case heavily embroiled the First Church of Charlestown and its minister, Reverend Charles Morton. Continue to the Cordis Mansion and walk through the preserved, stunning Federal-style brownstones away from the tourist crowds. Stop outside this massive estate built for wealthy hardware merchant Thomas Cordis. Learn how, for decades, this grand mansion was converted into the Norris & Son Funeral Home. Hear how long-time 'Townies' still remember attending wakes here, marking a time when Charlestown's grandest real estate served local community functions rather than billionaire investors. Next, head to the Bunker Hill Monument, a 221-foot granite obelisk marking the first major battle of the American Revolution. Learn how the 'Townie' bank robbery crews of the 1980s and 90s didn't just see a monument—they saw a tactical lookout point and a maze of narrow, one-way escape routes. Challenge yourself to the optional 294-step cardio climb to the top for the absolute best panoramic views of the Boston skyline and harbor. Then, dive headfirst into modern neighborhood history, local turf, and the fierce Irish loyalty that defined the 'Bank Robbery Capital of America'. Walk through the actual hidden backleys and neighborhood backdrops featured in Ben Affleck’s The Town and Johnny Depp's Black Mass. Contrast Hollywood's high-octane armor car chases against the real-life 'Code of Silence' and the deep-rooted community fabric of the 02129. Conclude the 250-year journey at the oldest tavern in Massachusetts (operating since 1780). This is the ultimate atmospheric closing note, where the line between colonial revolutionaries and the 20th-century 'old guard' completely blurs.

Includes

Guided walking tour Visit to USS Constitution Visit to City Square Park Visit to Cordis Mansion Visit to Bunker Hill Monument Visit to Warren Tavern Historical Homes

Excludes

Food and drinks

Important Information

  • The tour involves walking and climbing 294 steps at the Bunker Hill Monument ( if you choose) Wear comfortable shoes and bring water. Not suitable for people with mobility impairments, heart problems, or respiratory issues.

Easy cancellation

Cancel up to 24 hours in advance for a full refund

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