Portland True Crime Historical Walking Tour

Step into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journey through Portland’s underworld will leave you with spine-tingling stories you won’t soon forget. Dare to explore the city’s past? Book now—if you’re brave enough.

Meeting Point

Portland Beer Hub

320 Fore St, Portland, ME 04101, USA

Arrive 15 MINUTES before the start time of your tour.
Meet inside of the retail store, Portland Beer Hub (320 Fore Street, Portland, ME 04101), in downtown Portland's Old Port.

What's included:

• Water at Portland Beer Hub
• Engaging tales of Portland’s mobster history
• Guided walking tour with true crime stories

Not included:

• Gratuities for the guide

What to expect:

Duration: 2 hours

Old Port

Old Port, Portland, ME 04101, USA

Beneath the charm of Portland’s Old Port lies a darker story—one paved with cobblestones, secrets, and shadowy deals. This waterfront district once pulsed with illicit trade, backroom bribes, and speakeasies hidden in plain sight. As you stand among 19th-century brick facades and narrow alleys, it’s easy to imagine the bootleggers slipping through the night and the gangsters who ruled with intimidation. This stop peels back the polished surface to reveal the Old Port’s criminal underbelly—gritty, dangerous, and all too real.

2 hours