Bootleggers, Bosses & Bloodshed
Difficulty
moderate
Duration
2–2.5 hours
Fitness Level
Suitable for most ages with average fitness; expect light to moderate walking.
Overview
Step back into Portland’s Prohibition era with an inspiring walking tour that uncovers hidden stories of bootlegging, gangsters, and secret speakeasies. Perfect for history lovers and adventurers alike, this experience offers a thrilling journey through the city’s past.
Details
Discover Portland, Maine, in a whole new way with 'Bootleggers, Bosses & Bloodshed,' a captivating walking tour that brings history and local storytelling to life. Perfect for history buffs and adventure seekers alike, this experience takes you through the city's past during Prohibition, exploring notorious bootlegging routes, shadowy speakeasies, and legendary figures who shaped the era. As you walk through historic neighborhoods and hidden alleys, knowledgeable guides share engaging stories filled with intrigue, crime, and community spirit, making it more than just a tour—it's an immersive journey back in time. What sets this adventure apart is its combination of rich storytelling, off-the-beaten-path locations, and the chance to step into a pivotal chapter of Portland’s history. Whether you're a local wanting a deeper appreciation of your city or a visitor eager for authentic experiences, this tour offers a memorable glimpse into Maine’s clandestine past and vibrant culture. Comfortable walking shoes and curiosity are all you need to enjoy this exploration that connects the past with the present, leaving you with stories to share and a new perspective on Portland’s historic streets.
Adventure Tips
Wear comfortable footwear
The tour involves walking through historic neighborhoods; comfortable shoes are recommended for your comfort.
Bring a camera or smartphone
Capture the historic architecture and scenic streets along the tour route.
Arrive early.
Meeting times can be busy, so arriving a few minutes early ensures a smooth start.
Stay hydrated.
Carry water, especially during warmer months, to stay comfortable throughout the walk.
Local Insights
Hidden Gems
- The Old Port’s clandestine alleyways
- Historic vaults beneath the city streets
Wildlife
- Peregrine falcons
- Urban squirrels
History
Portland’s Prohibition-era history is rich, with secret speakeasies hidden in plain sight and legendary gangsters whose stories still fascinate locals.
Conservation
Efforts are ongoing to preserve Portland’s historic architecture and promote sustainable tourism that respects the city’s cultural heritage.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Portland Head Light from Fort Williams Park
- High Street’s historic buildings
What to Photograph
Recommended Gear
Walking shoes
Provide comfort and support for walking on uneven historic streets.
Weather-appropriate clothing
Layered clothing or rain gear depending on the season ensures comfort throughout the tour.
spring|summer|fall|winter specific
Camera or smartphone
Capture memorable moments and scenic spots along the route.
Water bottle
Stay hydrated during the walking adventure, especially on warmer days.
summer specific