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.
Mobsters & Lobsters: True Crime in Portland’s Old Port
🚶 Walking Tour 🧑🧑🧒🧒 All Ages 🕴️ Hidden Portland True Crime ⭐ Old Port Hidden Secrets!
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Adventure Photos
About This Adventure
Discover Portland's intriguing hidden history on a captivating tour that delves into its darker side. Starting at the Portland Beer Hub, you'll stroll through the streets while hearing gripping tales of mobsters and true crime, creating a unique sensory experience that blends local flavors with the city's tumultuous past.
Discover Portland's intriguing hidden history on a captivating tour that delves into its darker side. Starting at the Portland Beer Hub, you'll stroll through the streets while hearing gripping tales of mobsters and true crime, creating a unique sensory experience that blends local flavors with the city's tumultuous past.
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
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.
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Adventure Hotspots in Portland, Maine
Frequently Asked Questions
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