Old Port Historic Walking Tour
Portland, Maine Coast
About This Activity
Maine Day Ventures leads this 2-hour walking tour from Commercial Street through the Old Port, covering Portland's founding in 1632, the great fires that shaped the city's brick architecture, the rum riots of the 1850s, and the waterfront's working life. Guides are local historians with deep knowledge of the region. Small groups ensure a personal experience with time for questions.
Seasonal note: Year-round; check mainedayventures.com for current schedule
See This in an Itinerary
This activity appears in 28 of our curated itineraries.
Best 7 Days in Maine Coast — Without Nature
Portland → Kennebunkport → Midcoast Maine
Best 10 Days in Maine Coast — Without Nature
Portland → Kennebunkport → Midcoast Maine
Best 14 Days in Maine Coast
Portland → Kennebunkport → Midcoast Maine
Best 14 Days in Maine Coast — Walking Tours
Portland → Kennebunkport → Midcoast Maine
Best 14 Days in Maine Coast — History
Portland → Kennebunkport → Midcoast Maine
Best 14 Days in Maine Coast — Relaxed Pace
Portland → Kennebunkport
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