Private Tour: Discover Boston’s Dark Side in North End
Difficulty
easy
Duration
1.5 hours
Fitness Level
Suitable for most fitness levels since the tour is a moderate-paced walk without strenuous activity.
Overview
Uncover chilling true stories of Boston’s North End with a private 1.5-hour tour. Experience history’s darker events like the Great Influenza and Molasses Flood on this captivating walk.
Private Tour: The Dark Side of Boston
Hear tales of misery, misfortune and murder • 1.5 Hours
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About This Adventure
Embark on a captivating 1.5-hour journey through Boston's North End, where you'll uncover chilling tales of true historical events, including the Great Influenza and the Molasses Flood. This unique tour combines exploration with storytelling, revealing the darker side of Boston's oldest neighborhood. Perfect for groups seeking an unforgettable experience!
From April to mid-November, Private tours are bookable online for groups of up to 20 people with at least 1 week's notice. To request a private tour for groups of more than 20 people, or in the fall/winter, use the Private Tour Request form. Please provide at least 1-2 weeks notice in advance of your preferred tour date for larger groups.
Private tour request form link
Duration, Distance, Terrain
1.5 hours 1 mile at a moderate pace, stopping at various sites along the tour
About
On this tour through the North End’s winding streets and alleyways, you will hear tales of misery, misfortune, and murder. These dark stories are all based on true historical events that have occurred in Boston.
Learn about the Great Influenza of 1918, outbreaks of smallpox, the Molasses Flood, and the infamous Brink's Robbery against the backdrop of Boston's oldest neighborhood.
Exploring the North End is always a delight. It's even better when investigating stories from Boston's checkered past!
Meeting location:
Meet your guide at the corner of Hanover & Cross Streets, Boston (the statue of boxer Tony DeMarco across from the Greenway).
Finding Your Guide: All guides carry an 8×11 sign that says “Boston By Foot Walking Tours.”
Nearest MBTA Station: Haymarket (Orange & Green Lines)
What to bring
Comfortable shoes, dress for the weather, water bottle
Adventure Tips
Wear Comfortable Shoes
The tour involves walking on uneven cobblestone streets, so sturdy, comfortable footwear is important.
Bring a Light Jacket
Boston’s weather can be unpredictable; layering ensures comfort during cooler evenings or sudden temperature drops.
Arrive Early
Plan to arrive 10-15 minutes before the tour starts to check in and settle in comfortably.
Note Accessibility
Some areas have narrow sidewalks and uneven surfaces; check accessibility options if mobility is a concern.
Local Insights
Wildlife
- Sparrows common in the urban landscape
- Occasional sightings of squirrels in nearby parks
History
Boston’s North End is the city’s oldest neighborhood, known for its colonial history and stories tied to significant events like the 1919 Molasses Flood.
Conservation
Boston By Foot practices sustainable tourism by limiting group sizes and encouraging responsible behavior to preserve historic sites and neighborhood charm.
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Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Comfortable Walking Shoes
Supportive shoes help navigate uneven cobblestone streets safely and comfortably.
Light Jacket or Sweater
Keeps you warm during cooler spring evenings and sudden weather changes.
spring specific
Water Bottle
Stay hydrated during warmer months while exploring outdoors.
summer specific
Flashlight or Phone Light
Useful as the tour sometimes extends into twilight when natural light fades.
fall specific