• Old Port - Beneath the allure of Portland’s Old Port lies a more sinister tale—one marked by cobblestones, secrets, and clandestine dealings. This waterfront area once thrived on illegal trade, covert bribes, and speakeasies hidden in plain view. As visitors stand among the 19th-century brick buildings and narrow alleys, it’s easy to envision the bootleggers moving stealthily through the night and the gangsters who ruled through fear. This stop uncovers the polished exterior to reveal the Old Port’s criminal underworld—gritty, perilous, and all too real.

• Guided walking tour with true crime stories
• Engaging tales of True Crime in Portland Maine
• Local Guide
• Alcoholic beverages
• Water at Portland Beer Hub

• Gratuities for the guide
• Food

Embark on a journey into the mysterious past of Portland with this captivating true crime tour, where hidden secrets lie behind historic facades and cobblestone streets echo with tales of corruption, violence, and vice. Encounter the world of ruthless mobsters, cunning bootleggers, ambitious bosses, and shocking scandals as this tour reveals the darker side of Maine’s largest city. Stroll along the very streets where speakeasies flourished, clandestine deals were struck under the cover of night, and power struggles led to bloodshed. Guided by knowledgeable experts, this exploration of Portland’s underworld promises spine-chilling stories that will linger in your memory. Are you ready to delve into the city’s past? Book your adventure now—if you dare.

For a full refund, cancel at least 24 hours before the scheduled departure time.